Chicago

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deep-dish to tavern-cut, the Loop to Pullman

The Loop & Downtown 98 places · area 1 of 9

River North, Streeterville, Gold Coast, South Loop, Museum Campus, West Loop

1 Must see within The Loop & Downtown · Pizza

Lou Malnati's Pizzeria (River North)

The family that helped invent deep dish (Lou worked at Uno before opening his own in 1971); Infatuation calls it the best version of the classic Chicago pie — sauce on top, flaky buttery crust.
439 N Wells St, Chicago, IL 60654

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Photo: Marlene Calderon · CC BY-SA 3.0 · Wikimedia Commons (resized)

2 Must see within The Loop & Downtown

The Rookery

Burnham & Root's 1888 LaSalle Street landmark, whose skylit light court was remodelled by Frank Lloyd Wright in 1905 — the spiral oriel staircase is the money shot.
Look for architecture building frank lloyd wright landmark
209 S LaSalle St, Chicago, IL 60604

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Photo: Sea Cow · CC BY-SA 4.0 · Wikimedia Commons (resized)

3 Must see within The Loop & Downtown

Shedd Aquarium

1930 Beaux-Arts aquarium on Museum Campus — 32,000 animals, beluga whales and Pacific white-sided dolphins in the lake-view Abbott Oceanarium.
Look for aquarium museum family
1200 S Lake Shore Dr, Chicago, IL 60605

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Photo: Alanscottwalker · CC BY-SA 4.0 · Wikimedia Commons (resized)

4 Must see within The Loop & Downtown

Chicago Architecture Center

The city's architecture HQ on the river — supersized skyscraper models, the lit-up downtown model, and the departure dock for its famous 90-minute First Lady river cruise.
Look for museum architecture river cruise
111 E Wacker Dr, Chicago, IL 60601

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Photo: victorgrigas · CC BY-SA 3.0 · Wikimedia Commons (resized)

5 Must see within The Loop & Downtown

Old Town Ale House

Old Town dive by Second City — walls of regulars' portraits, a Bourdain favourite.
219 W North Ave, Chicago, IL 60610

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6 Must see within The Loop & Downtown

Au Cheval

West Loop diner whose cheeseburger Thrillist ranked among America's best — the most hyped burger in Chicago.
800 W Randolph St, Chicago, IL 60607

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7 Must see within The Loop & Downtown

The Publican

Paul Kahan's 2008 Fulton Market beer hall of pork, oysters and beer — the restaurant that helped turn the meatpacking district into a dining destination.
837 W Fulton Market, Chicago, IL 60607

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8 Must see within The Loop & Downtown · Italian

Italian Village

Chicago's oldest Italian restaurant (1927), opened by Lucca-born Alfredo Capitanini and run by the fourth generation — a pre-opera Loop institution.
71 W Monroe St, Chicago, IL 60603

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Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

9 Must see within The Loop & Downtown

Art Institute of Chicago

One of the world's great art museums — 300,000 works including Seurat's La Grande Jatte, Hopper's Nighthawks and Wood's American Gothic.
Look for museum art gallery
111 S Michigan Ave, Chicago, IL 60603

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Photo: Joe Ravi · CC BY-SA 3.0 · Wikimedia Commons (resized)

10 Must see within The Loop & Downtown

Field Museum

The 1893-born natural history museum on the Museum Campus — home of SUE the T. rex and Máximo the titanosaur.
Look for museum family dinosaurs
1400 S DuSable Lake Shore Dr, Chicago, IL 60605

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Photo: Highsmith, Carol M., 1946-, photographer · Public domain · loc.gov

11 Must see within The Loop & Downtown

Willis Tower Skydeck

The 103rd-floor observation deck of the former Sears Tower, with The Ledge glass boxes 1,353 ft over Wacker Drive.
Look for skydeck observation icon skyline
233 S Wacker Dr, Chicago, IL 60606

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12 Must see within The Loop & Downtown

Cloud Gate (The Bean)

Anish Kapoor's mirror-polished 'Bean' in Millennium Park — the requisite Chicago selfie, beside Gehry's Pritzker Pavilion and the Lurie Garden. Free.
Look for public art sculpture icon park free
Millennium Park, 201 E Randolph St, Chicago, IL 60602

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Photo: Hbodine · CC BY-SA 4.0 · Wikimedia Commons (resized)

13 Must see within The Loop & Downtown

Navy Pier

The 1916 pier stretching into Lake Michigan, with the 200-ft Centennial Wheel, the Chicago Children's Museum and boat departures.
Look for pier lake michigan icon family
600 E Grand Ave, Chicago, IL 60611

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Photo: H. Michael Miley from Schaumburg, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

14 Must see within The Loop & Downtown

Buckingham Fountain

Grant Park's 1927 Versailles-inspired fountain, one of the largest in the world, with summer light-and-water shows. Free.
Look for fountain park icon free
301 S Columbus Dr, Chicago, IL 60605

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Photo: Sea Cow · CC BY-SA 4.0 · Wikimedia Commons (resized)

15 Must see within The Loop & Downtown

Adler Planetarium

The first planetarium in the Western Hemisphere (1930), at the tip of Northerly Island's peninsula with a classic skyline view.
Look for planetarium museum family skyline
1300 S DuSable Lake Shore Dr, Chicago, IL 60605

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Photo: ajay_suresh · CC BY 2.0 · Wikimedia Commons (resized)

16 Must see within The Loop & Downtown

Chicago Cultural Center

The 1897 former public library, now the nation's first free municipal cultural center — under the world's largest Tiffany glass dome (38 ft, ~30,000 pieces).
Look for cultural center architecture free tiffany
78 E Washington St, Chicago, IL 60602

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Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

17 Must see within The Loop & Downtown

Tribune Tower

Hood & Howells' 1925 Gothic tower from the 'most beautiful building in the world' competition, its base studded with ~150 fragments of famous buildings (Westminster Abbey, the Great Wall, the Parthenon).
Look for architecture tower gothic landmark
435 N Michigan Ave, Chicago, IL 60611

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18 Must see within The Loop & Downtown

360 Chicago (875 North Michigan Avenue)

The tapering, X-braced former John Hancock Center (1969), with the 94th-floor 360 Chicago observation deck and TILT.
Look for observation skyline tower icon
875 N Michigan Ave, Chicago, IL 60611

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Photo: Diego Delso · CC BY-SA 3.0 · Wikimedia Commons (resized)

19 Must see within The Loop & Downtown

Marina City

Bertrand Goldberg's 1963 'corncob' towers on the river — at opening the tallest residential and tallest concrete buildings in the world.
Look for architecture river tower landmark
300 N State St, Chicago, IL 60654

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Photo: JeremyA · CC BY-SA 2.5 · Wikimedia Commons (resized)

20 Must see within The Loop & Downtown

Museum of Contemporary Art Chicago

One of the largest contemporary art museums in the world, in Streeterville off the Mag Mile; Tuesday summer jazz on the terrace.
Look for museum art gallery
220 E Chicago Ave, Chicago, IL 60611

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21 Must see within The Loop & Downtown

Buddy Guy's Legends

The South Loop blues club owned by Buddy Guy himself — live blues every night and his own January residency.
Look for blues club music
700 S Wabash Ave, Chicago, IL 60605

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Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

22 Must see within The Loop & Downtown

Millennium Park

The 24.5-acre front lawn of Chicago (2004) — Cloud Gate, Crown Fountain, Gehry's Pritzker Pavilion and the hidden Lurie Garden, with free summer concerts.
Look for park public art landmark
N Michigan Ave between Randolph St and Monroe St, Chicago, IL 60602

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23 Must see within The Loop & Downtown

Auditorium Theatre

Adler & Sullivan's 1889 Auditorium Building — a National Historic Landmark with a gold-leafed arched hall and famous acoustics.
Look for theatre architecture sullivan landmark
50 E Ida B. Wells Dr, Chicago, IL 60605

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24 Must see within The Loop & Downtown

Crown Fountain

Jaume Plensa's twin 50-ft glass-block towers in Millennium Park, projecting faces of Chicagoans who spout water into the splash pool. Free.
Look for fountain public art park free family
Millennium Park, 201 E Randolph St, Chicago, IL 60602

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25 Must see within The Loop & Downtown

The Chicago Picasso

Picasso's untitled 50-ft Cor-ten steel sculpture (1967) in Daley Plaza — baboon, woman or dog, he never said. Free.

Look for public art sculpture picasso free

Daley Plaza, 50 W Washington St, Chicago, IL 60602

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26 Must see within The Loop & Downtown

Maggie Daley Park

20 acres east of Millennium Park — the climbing walls, the winter skating ribbon, mini golf and a giant playground. Free.

Look for park playground family free

337 E Randolph St, Chicago, IL 60601

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27 Must see within The Loop & Downtown

Chicago Riverwalk

The 1.25-mile path along the river's main branch — wine bars, kayak rentals and the city's best architecture at water level. Free.

Look for riverwalk river free

Chicago River (main branch), Lake St to Lake Shore Dr, Chicago, IL 60601

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28 Must see within The Loop & Downtown

Wrigley Building

The 1924 white-terracotta twin towers with a Giralda-style clock tower — the first skyscraper on the new Michigan Avenue, floodlit at night.

Look for architecture building landmark icon

400 N Michigan Ave, Chicago, IL 60611

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29 Must see within The Loop & Downtown

Chicago Board of Trade Building

Holabird & Root's 1930 Art Deco tower closing the LaSalle Street canyon, crowned by John Storrs's faceless aluminium Ceres.

Look for architecture building art deco landmark

141 W Jackson Blvd, Chicago, IL 60604

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30 Must see within The Loop & Downtown

Sullivan Center

Louis Sullivan's 1899–1904 Carson Pirie Scott store at State & Madison — the cast-iron prairie-foliage entrance rotunda is the masterpiece.

Look for architecture building sullivan landmark

1 S State St, Chicago, IL 60603

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31 Must see within The Loop & Downtown

Civic Opera House (Lyric Opera)

Samuel Insull's 1929 Art Deco 'throne' on the river, its gilded hall home to the Lyric Opera since 1954.

Look for opera theatre art deco architecture

20 N Upper Wacker Dr, Chicago, IL 60606

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32 Must see within The Loop & Downtown

Symphony Center

Orchestra Hall (1904) on Michigan Avenue, home of the world-famous Chicago Symphony Orchestra.

Look for symphony concert music

220 S Michigan Ave, Chicago, IL 60604

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33 Must see within The Loop & Downtown

The Berghoff

German restaurant and bar in the Loop since 1898 — its bar held Chicago's first post-Prohibition liquor license. A James Beard America's Classics honoree.

17 W Adams St, Chicago, IL 60603

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34 Must see within The Loop & Downtown

Gene & Georgetti

River North steakhouse in its wood-frame building since 1941 — as old-school as Chicago gets (Infatuation), rib eye on Chicago Magazine's Iconic Eats.

500 N Franklin St, Chicago, IL 60654

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35 Must see within The Loop & Downtown

Manny's Cafeteria & Delicatessen

South Loop cafeteria deli since 1942, lunchroom of generations of politicians — reviewed by the Infatuation ('still great after 80 years') and on Chicago Magazine's Iconic Eats for its corned beef.

1141 S Jefferson St, Chicago, IL 60607

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36 Must see within The Loop & Downtown

Billy Goat Tavern

Lower Michigan Avenue newspapermen's tavern since 1934 — 'cheezborger, cheezborger, no Pepsi, Coke' of SNL fame and the Cubs' goat curse.

430 N Michigan Ave (lower level), Chicago, IL 60611

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Gino's East Pizzeria, Chicago, Illinois (11004579043) — Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

37 Must see within The Loop & Downtown · Pizza

Gino's East (Superior St)

Deep-dish institution since 1966 near the Mag Mile, its cornmeal-crust pies served in graffiti-covered booths diners are invited to sign.

162 E Superior St, Chicago, IL 60611

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38 Must see within The Loop & Downtown

Mr. Beef

The River North beef stand (since 1979) that inspired The Bear's Original Beef of Chicagoland — dipped beef with hot giardiniera.

666 N Orleans St, Chicago, IL 60654

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39 Must see within The Loop & Downtown

Girl & the Goat

Stephanie Izard's Randolph Street flagship (2010) that made the West Loop a dining district — the pig-face plate is one of Chicago Magazine's 50 Iconic Eats.

809 W Randolph St, Chicago, IL 60607

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40 Must see within The Loop & Downtown

Avec

Paul Kahan's cedar-lined Mediterranean wine bar (2003) — its chorizo-stuffed, bacon-wrapped dates are one of Chicago Magazine's 50 Iconic Eats.

615 W Randolph St, Chicago, IL 60661

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41 Must see within The Loop & Downtown

Greek Islands

Greektown's taverna since 1971 — flaming saganaki ('Opa!') is one of Chicago Magazine's 50 Iconic Eats.

200 S Halsted St, Chicago, IL 60661

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42 Must see within The Loop & Downtown

Oriole

Noah Sandoval's hidden West Loop tasting room behind a freight elevator — two Michelin stars (2025).

661 W Walnut St, Chicago, IL 60661

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43 Must see within The Loop & Downtown · Mexican

Frontera Grill

Rick Bayless's 1987 River North original that put regional Mexican cooking on America's map — in the Michelin Guide.

445 N Clark St, Chicago, IL 60654

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44 Must see within The Loop & Downtown

Lou Mitchell's

The 1923 diner at the start of Route 66 — free Milk Duds and donut holes while you wait for double-yolk eggs; in the Michelin Guide.

565 W Jackson Blvd, Chicago, IL 60661

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45 Must see within The Loop & Downtown · Japanese

Kumiko

Julia Momosé's Japanese cocktail bar and dining room in the West Loop — in the Michelin Guide.

630 W Lake St, Chicago, IL 60661

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46 Must see within The Loop & Downtown · Pizza

Pizzeria Uno

Where Ike Sewell's 1943 pizzeria is credited with launching Chicago deep dish — the original still stands at Ohio & Wabash.

29 E Ohio St, Chicago, IL 60611

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47 Must see within The Loop & Downtown

Smyth

West Loop tasting-menu restaurant tied to a family farm — Chicago's only three-Michelin-star restaurant in the 2025 guide.

177 N Ada St, Chicago, IL 60607

48 Must see within The Loop & Downtown

Ever

Curtis Duffy's Fulton Market tasting room — two Michelin stars; its GM Amy Cordell won Michelin's 2025 service award.

1340 W Fulton St, Chicago, IL 60607

49 Must see within The Loop & Downtown · Mexican

Topolobampo

Rick Bayless's fine-dining room behind Frontera Grill in River North — one Michelin star.

445 N Clark St, Chicago, IL 60654

50 Worth the detour within The Loop & Downtown

Old St. Patrick's Church

Chicago's oldest public building (1856) and a Great Fire survivor — Celtic-revival windows and Book of Kells-inspired stencils in the West Loop.

Look for church history landmark

700 W Adams St, Chicago, IL 60661

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51 Worth the detour within The Loop & Downtown

Marquette Building

Holabird & Roche's 1895 Chicago School landmark — Tiffany mosaics of Père Marquette's voyage and Edward Kemeys bronzes in the lobby.

Look for architecture skyscraper landmark

S Dearborn St at W Adams St, the Loop, Chicago

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52 Worth the detour within The Loop & Downtown

Clarke House Museum

Chicago's oldest house (1836), the Greek Revival home of Henry & Caroline Clarke, now a city-run museum in the Prairie Avenue district.

Look for museum house history

1827 S Indiana Ave, Chicago, IL 60616

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53 Worth the detour within The Loop & Downtown

Carbide & Carbon Building

The Burnham brothers' 1929 black-granite and gold-leaf Art Deco tower — said to be modelled on a champagne bottle — now the Pendry hotel with a rooftop bar.

Look for architecture art deco landmark

N Michigan Ave, the Loop, Chicago (Pendry Chicago hotel)

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54 Worth the detour within The Loop & Downtown

Goodman Theatre

Chicago's oldest and largest not-for-profit theatre (1925), in the Loop theatre district.

Look for theatre arts

170 N Dearborn St, Chicago, IL 60601

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55 Worth the detour within The Loop & Downtown

Gibsons Bar & Steakhouse

Rush Street power steakhouse since 1989 — consistently among the top-grossing independent restaurants in the US.

1028 N Rush St, Chicago, IL 60611

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56 Worth the detour within The Loop & Downtown · Pizza

Exchequer Restaurant & Pub

Family-run Loop pub since 1969 in a reputed Capone-era speakeasy — a less-crowded deep-dish alternative a block from Miller's Pub.

226 S Wabash Ave, Chicago, IL 60604

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57 Worth the detour within The Loop & Downtown

Chicago Water Tower

The 1869 limestone water tower that survived the Great Chicago Fire, now a free city art gallery on the Mag Mile.

Look for historic landmark gallery free

806 N Michigan Ave, Chicago, IL 60611

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58 Worth the detour within The Loop & Downtown

Chicago Theatre

The 1921 French Baroque movie palace under the six-storey C-H-I-C-A-G-O marquee on State Street.

Look for theatre historic landmark

175 N State St, Chicago, IL 60601

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59 Worth the detour within The Loop & Downtown

Jay Pritzker Pavilion

Frank Gehry's ribbon-steel bandshell in Millennium Park — free summer concerts (Grant Park Music Festival) and movies on the lawn.

Look for music concert park free pavilion

201 E Randolph St, Chicago, IL 60602

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60 Worth the detour within The Loop & Downtown

Andy's Jazz Club

One of the city's best-known jazz rooms, two blocks off the Mag Mile, with nightly sets and jam sessions.

Look for jazz club music

11 E Hubbard St, Chicago, IL 60611

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exterior entrance of the Driehaus Museum — Photo: Lmh9y6 · CC BY-SA 3.0 · Wikimedia Commons (resized)

61 Worth the detour within The Loop & Downtown

Richard H. Driehaus Museum

The 1883 Nickerson 'Marble Palace' — marble floors, grand staircases and Gilded Age decorative arts, a block off Michigan Avenue.

Look for museum house gilded age

E Erie St, River North, Chicago (Nickerson Mansion)

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62 Worth the detour within The Loop & Downtown

Soldier Field

The Bears' colonnaded 1924 lakefront stadium (with its 2003 'spaceship' bowl), also home of the Chicago Fire.

Look for stadium bears sport

1410 Special Olympics Dr, Chicago, IL 60605

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63 Worth the detour within The Loop & Downtown

Glessner House

H. H. Richardson's 1887 Romanesque fortress-house on Prairie Avenue, a museum of the Gilded Age.

Look for house museum architecture historic

1800 S Prairie Ave, Chicago, IL 60616

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64 Worth the detour within The Loop & Downtown

Monadnock Building

Burnham & Root's 1891 load-bearing brick skyscraper — 'the first modern building' — with Holabird & Roche's steel-frame 1893 addition.

Look for architecture building landmark

53 W Jackson Blvd, Chicago, IL 60604

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65 Worth the detour within The Loop & Downtown

Chicago Union Station

The 1925 Beaux-Arts station whose Great Hall rises under a 219-ft barrel-vaulted skylight — the Untouchables staircase.

Look for station architecture movie

225 S Canal St, Chicago, IL 60606

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66 Worth the detour within The Loop & Downtown

Flamingo (Calder)

Alexander Calder's 53-ft red stabile (1974) set against Mies van der Rohe's black Federal Center. Free.

Look for public art sculpture calder free

Federal Plaza, 50 W Adams St, Chicago, IL 60603

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67 Worth the detour within The Loop & Downtown

Four Seasons (Chagall)

Marc Chagall's 70-ft mosaic box (1974) of six Chicago scenes in 250 colours. Free.

Look for public art mosaic chagall free

Chase Tower Plaza, 10 S Dearborn St, Chicago, IL 60603

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68 Worth the detour within The Loop & Downtown

Newberry Library

Independent research library (1887) facing Washington Square — free exhibitions from 1.6 million books and 600,000 maps.

Look for library free historic

60 W Walton St, Chicago, IL 60610

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69 Worth the detour within The Loop & Downtown

Harold Washington Library Center

The world's largest public library building at opening (1991), with owl-topped acroterions and a 9th-floor winter garden. Free.

Look for library architecture free

400 S State St, Chicago, IL 60605

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70 Worth the detour within The Loop & Downtown

Oak Street Beach

The Gold Coast beach at the top of the Mag Mile, tucked under the skyline. Free.

Look for beach lakefront skyline free

1000 N Lake Shore Dr, Chicago, IL 60611

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71 Worth the detour within The Loop & Downtown

12th Street Beach

Small crescent beach on Northerly Island behind the Adler, with panoramic lake views. Free.

Look for beach lakefront free

1200 S Linn White Dr, Chicago, IL 60605

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72 Worth the detour within The Loop & Downtown

Northerly Island

The man-made peninsula (the old Meigs Field) re-wilded with prairie paths, fishing spots and skyline views. Free.

Look for park nature lakefront skyline free

1521 S Linn White Dr, Chicago, IL 60605

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73 Worth the detour within The Loop & Downtown

Holy Name Cathedral

The Archdiocese's 1875 Gothic Revival cathedral by Patrick Keely, with the cardinals' galeros hanging from the ceiling.

Look for cathedral church architecture

735 N State St, Chicago, IL 60611

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74 Worth the detour within The Loop & Downtown

Merchandise Mart

The 1930 Art Deco 'Mart' on the river — once the largest building in the world, with Jules Guérin murals inside and Art on the Mart projections on its facade at night.

Look for architecture building art deco river

222 W Merchandise Mart Plaza, Chicago, IL 60654

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75 Worth the detour within The Loop & Downtown

Reliance Building

Atwood's 1895 terracotta-and-glass tower — a prototype of the glass skyscraper and the Chicago window (now a hotel).

Look for architecture building landmark

1 W Washington St, Chicago, IL 60602

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76 Worth the detour within The Loop & Downtown

Aqua Tower

Jeanne Gang's 2009 tower whose rippling white balconies look like water cascading down its sides.

Look for architecture tower skyline

225 N Columbus Dr, Chicago, IL 60601

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77 Worth the detour within The Loop & Downtown

Palmer House

Chicago's oldest continually operating hotel — the gilded lobby ceiling and Tiffany fittings; birthplace of the brownie.

Look for hotel historic architecture landmark

17 E Monroe St, Chicago, IL 60603

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78 Worth the detour within The Loop & Downtown

Chicago Shakespeare Theater

The Tony-winning Shakespeare company at the end of Navy Pier.

Look for theatre arts pier

800 E Grand Ave (Navy Pier), Chicago, IL 60611

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79 Worth the detour within The Loop & Downtown

Ceres Cafe

The traders' bar in the Board of Trade lobby, notorious for a 'jack and coke' that's a giant cup of whiskey with the can on the side.

141 W Jackson Blvd, Chicago, IL 60604

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80 Worth the detour within The Loop & Downtown · Mexican

Taqueria Chingón

Reopened CDMX-style taqueria from Marcos Ascencio and Oliver Poilevey — Michelin Bib Gourmand 2025.

817 W Fulton Market, Chicago, IL 60607

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81 Worth the detour within The Loop & Downtown

Grant Achatz's Fulton Market restaurant that reinvents its whole menu and theme every few months — in the Michelin Guide.

953 W Fulton Market, Chicago, IL 60607

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82 Worth the detour within The Loop & Downtown

Elske

David and Anna Posey's Danish-inflected West Loop restaurant with an open-air fireplace courtyard — in the Michelin Guide.

1350 W Randolph St, Chicago, IL 60607

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83 Worth the detour within The Loop & Downtown

Sepia

Andrew Zimmerman's West Loop dining room in a 19th-century print shop — one Michelin star (2025).

123 N Jefferson St, Chicago, IL 60661

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84 Worth the detour within The Loop & Downtown · Japanese

Mako

West Loop omakase counter — a Michelin-recognised Japanese tasting menu.

731 W Lake St, Chicago, IL 60661

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85 Worth the detour within The Loop & Downtown

Sifr

River North live-fire Middle Eastern restaurant — Michelin Bib Gourmand.

660 N Orleans St, Chicago, IL 60654

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86 Worth the detour within The Loop & Downtown

Three Dots and a Dash

Below-street River North tiki bar — #27 on the World's 50 Best Bars (2014).

435 N Clark St, Chicago, IL 60654

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87 Worth the detour within The Loop & Downtown · Italian

Monteverde

James Beard-winning chef Sarah Grueneberg's West Loop pasta house (2015), with sheets rolled and hung daily in view of the counter.

1020 W Madison St, Chicago, IL 60607

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88 Worth the detour within The Loop & Downtown

Miller's Pub

Loop pub since 1935 under the Wabash 'L' — signed photos from Sinatra to Monroe and one of the Loop's few late-night kitchens.

134 S Wabash Ave, Chicago, IL 60603

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89 Worth the detour within The Loop & Downtown

Moody Tongue

South Loop brewery whose dining room above the brewhouse holds one Michelin star.

2515 S Wabash Ave, Chicago, IL 60616

90 Worth the detour within The Loop & Downtown · Indian & Pakistani

Indienne

Sujan Sarkar's River North modern-Indian tasting room — one Michelin star.

217 W Huron St, Chicago, IL 60654

91 Worth the detour within The Loop & Downtown

Cabra

Stephanie Izard's Peruvian rooftop in the West Loop — Michelin Bib Gourmand (Chicago 2024).

200 N Green St, Chicago, IL 60607

92 Worth the detour within The Loop & Downtown

Gilt Bar

River North gastropub — Michelin Bib Gourmand (Chicago 2024).

230 W Kinzie St, Chicago, IL 60654

93 Worth the detour within The Loop & Downtown

The Purple Pig

Magnificent Mile Mediterranean small-plates room — Michelin Bib Gourmand (Chicago 2024).

444 N Michigan Ave, Chicago, IL 60611

94 Worth the detour within The Loop & Downtown · Japanese

Momotaro

Boka Group's West Loop Japanese canteen with multiple kitchens (exec. chef Gene Kato) — in the Michelin Guide.

820 W Lake St, Chicago, IL 60607

95 Worth the detour within The Loop & Downtown · Japanese

Omakase Yume

Chef Sangtae Park's intimate West Loop omakase — in the Michelin Guide.

651 W Washington Blvd, Chicago, IL 60661

96 Deep cut within The Loop & Downtown

Second Presbyterian Church

Gothic Revival church re-done inside in Arts & Crafts style by Howard Van Doren Shaw after a 1900 fire — 21 stained-glass windows, nine by Tiffany (NHL).

Look for church arts and crafts landmark

S Michigan Ave, Prairie Avenue district, Chicago

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97 Deep cut within The Loop & Downtown

Chicago Temple (Sky Chapel)

The 1924 First United Methodist 'Chicago Temple' — the world's tallest church building, with a tiny Sky Chapel in its spire 400 ft above the Loop.

Look for church skyscraper landmark

W Washington St, the Loop, Chicago

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98 Deep cut within The Loop & Downtown · Italian

Harry Caray's Italian Steakhouse

River North steakhouse (1987) named for the Cubs broadcaster, in a building once home to Capone enforcer Frank Nitti.

33 W Kinzie St, Chicago, IL 60654

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North Side 70 places · area 2 of 9

Lincoln Park, Lakeview, Lincoln Square, Uptown & Argyle, Andersonville, Rogers Park & Devon

South Pond in Lincoln Park — Photo: Alanscottwalker · CC BY-SA 3.0 · Wikimedia Commons (resized)

1 Must see within North Side

Lincoln Park (lakefront park)

Chicago's largest park (1868) — seven miles of lakefront with the free zoo, conservatory, North Pond, Caldwell Lily Pool, beaches and the Lakefront Trail.

Look for park lakefront nature

Lakefront from North Ave to Ardmore Ave, Chicago (Chicago Park District)

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2 Must see within North Side · Chinese

Sun Wah Bar-B-Q

Uptown Hong Kong barbecue house near Argyle, family-run since 1987; 2018 James Beard America's Classics award.

5039 N Broadway, Chicago, IL 60640

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3 Must see within North Side

Kingston Mines

Chicago's oldest and largest continuously running blues club (1968) — two stages, alternating sets until 4 a.m.

Look for blues club music

2548 N Halsted St, Chicago, IL 60614

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ChicagoNature (6) — Photo: Alanscottwalker · CC BY-SA 3.0 · Wikimedia Commons (resized)

4 Must see within North Side

Peggy Notebaert Nature Museum

The Chicago Academy of Sciences' museum in Lincoln Park, built around the 2,700-sq-ft Judy Istock Butterfly Haven.

Look for museum nature family

2430 N Cannon Dr, Chicago, IL 60614

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beach overview from Hancock — Photo: J. Miers · CC BY-SA 1.0 · Wikimedia Commons (resized)

5 Must see within North Side

North Avenue Beach

Chicago's busiest beach, by Lincoln Park — the ocean-liner beach house, volleyball, paddleboards and the classic skyline-across-the-sand view. Free.

Look for beach lakefront skyline free

1600 N Lake Shore Dr, Chicago, IL 60614

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6 Must see within North Side

Elks National Veterans Memorial

The domed 1926 Beaux-Arts memorial in Lincoln Park — marble rotunda, Eugene Savage murals and heroic friezes; one of WTTW's 'Most Beautiful Places'. Free.

Look for memorial architecture landmark free

2750 N Lakeview Ave, Chicago, IL 60614

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7 Must see within North Side

Alfred Caldwell Lily Pool

Caldwell's 1938 Prairie-style 'hidden garden' in Lincoln Park — stratified stone, a prairie river and a waterfall; a National Historic Landmark, open April–October. Free.

Look for garden park prairie school landmark free

125 W Fullerton Pkwy, Chicago, IL 60614

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8 Must see within North Side

Metro

Wrigleyville's 1927 theatre turned rock club (since 1982) — midsize touring acts upstairs, Smart Bar downstairs.

Look for music club concert

3730 N Clark St, Chicago, IL 60613

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9 Must see within North Side · Pizza

Pequod's Pizza

Lincoln Park's pan-pizza bar whose pies are ringed with blackened, caramelized cheese — the deep dish many Chicagoans name first (Infatuation) and #8 on Time Out's citywide pizza ranking.

2207 N Clybourn Ave, Chicago, IL 60614

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10 Must see within North Side

Svea Restaurant

Andersonville's tiny Swedish breakfast room with Viking art — the last of the neighbourhood's old Swedish diners.

5236 N Clark St, Chicago, IL 60640

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11 Must see within North Side · Mexican

Huaraches Doña Chio

Six-table Edgewater counter where masa is patted and griddled to order — called the best huaraches in Chicago. Cash only.

1547 W Elmdale Ave, Chicago, IL 60660

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12 Must see within North Side · Pizza

Spacca Napoli

Ravenswood's Neapolitan pizzeria with a quiet side-street patio — No. 14 in 50 Top Pizza USA 2023 and on its world top-100.

1769 W Sunnyside Ave, Chicago, IL 60640

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13 Must see within North Side · Indian & Pakistani

Ghareeb Nawaz

Devon Avenue's beloved cheap-eats institution — rich Indian/Pakistani plates at rock-bottom prices, open late.

2032 W Devon Ave, Chicago, IL 60659

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14 Must see within North Side

Wrigley Field

The Cubs' ivy-walled ballpark (1914), the second-oldest in the majors, with its hand-turned scoreboard and Wrigleyville rooftops.

Look for ballpark stadium cubs sport

1060 W Addison St, Chicago, IL 60613

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15 Must see within North Side

Lincoln Park Zoo

One of the country's oldest zoos (1868) and still free, with the Farm-in-the-Zoo and Nature Boardwalk.

Look for zoo park family free

2001 N Clark St, Chicago, IL 60614

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16 Must see within North Side

Green Mill Cocktail Lounge

Uptown's 1907 former Capone-era speakeasy, one of the oldest continuously operating jazz clubs in the country; home of the Uptown Poetry Slam.

Look for jazz club speakeasy cocktail bar music

4802 N Broadway, Chicago, IL 60640

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17 Must see within North Side

The Second City

Old Town's improv theatre (1959) that launched Belushi, Murray, Fey, Colbert and Carell.

Look for comedy theater improv

1616 N Wells St, Chicago, IL 60614

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18 Must see within North Side

Steppenwolf Theatre Company

The ensemble theatre founded in 1974 by Gary Sinise, Terry Kinney and Jeff Perry — Tony-winning home of Malkovich, Metcalf and 'August: Osage County'.

Look for theater theatre

1650 N Halsted St, Chicago, IL

19 Must see within North Side

Lincoln Park Conservatory

The 1890s Victorian glasshouse in Lincoln Park — palms, ferns and orchids, free and open year-round.

Look for conservatory garden park free

2391 N Stockton Dr, Chicago, IL 60614

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20 Must see within North Side

Music Box Theatre

The 1929 Southport movie palace with a starry-sky ceiling and a live organist between shows — Chicago's leading independent cinema.

Look for theatre movie historic

3733 N Southport Ave, Chicago, IL 60613

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21 Must see within North Side

Wolfy's

West Ridge stand famous since 1967 for its sign — a giant hot dog on a fork — and a char dog both the Infatuation and Time Out rank among the city's best.

2734 W Peterson Ave, Chicago, IL 60659

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22 Must see within North Side

Twin Anchors Restaurant & Tavern

Old Town rib tavern open since 1932 (a Sinatra hangout), neon beer signs intact — on the Infatuation's old-school list and Chicago Magazine's Iconic Eats for its baby backs.

1655 N Sedgwick St, Chicago, IL 60614

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23 Must see within North Side

Alinea

Grant Achatz's Lincoln Park landmark of modernist cooking, 20 years old — two Michelin stars in 2025 (down from three).

1723 N Halsted St, Chicago, IL 60614

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24 Must see within North Side

North Pond

An Arts & Crafts warming shelter on a Lincoln Park pond turned seasonal-Midwest tasting room with a skyline view — in the Michelin Guide.

2610 N Cannon Dr, Chicago, IL 60614

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25 Must see within North Side · Mexican

Cariño

Norman Fenton's Uptown Latin American tasting menu and 'taco omakase' — Michelin-starred (Time Out's 2024 star list) and in the 2025 guide.

4662 N Broadway, Chicago, IL 60640

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26 Must see within North Side

Hopleaf

Andersonville Belgian beer bar — Time Out Chicago's Best Beer Bar; a fixture of Chicago craft-beer guides.

5148 N Clark St, Chicago, IL 60640

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27 Must see within North Side

Lost Larson

Andersonville bakery-café honouring the neighbourhood's Swedish roots (chef Bobby Schaffer mills his own flour).

5318 N Clark St, Chicago, IL 60640

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28 Must see within North Side · Korean

Cho Sun Ok

Korean institution since 1988 on the old Lincoln Ave Koreatown strip.

4200 N Lincoln Ave, Chicago, IL 60618

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29 Must see within North Side

Sweet Mandy B's

Lincoln Park's retro-pastel bakery — the city's go-to for old-fashioned buttercream cupcakes and bars.

1208 W Webster Ave, Chicago, IL 60614

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30 Must see within North Side

Galit

Zach Engel's modern Middle Eastern restaurant in Lincoln Park — one Michelin star.

2429 N Lincoln Ave, Chicago, IL 60614

31 Must see within North Side · Mexican

Kie-Gol-Lanee

Uptown restaurant cooking the food of the Zapotec Sierra Norte of Oaxaca — Michelin Bib Gourmand.

5004 N Sheridan Rd, Chicago, IL 60640

32 Worth the detour within North Side

Old Town School of Folk Music

Folk-music school and concert hall (founded 1957) in a restored 1929 library building on Lincoln Square's main street.

Look for music concert

4545 N Lincoln Ave, Chicago, IL 60625

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33 Worth the detour within North Side

Alta Vista Terrace District

'Street of Forty Doors' — a single block of London-style rowhouses (1900–04) mirrored end to end; Chicago's first designated historic district (1971), steps from Wrigley Field.

Look for historic district architecture

Alta Vista Terrace, Lakeview (Wrigleyville), Chicago, IL 60613

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34 Worth the detour within North Side

Andersonville Commercial District

The old Swedish village on Clark Street — indie shops, Swedish bakeries and the flag-painted water tower; Time Out once voted it the coolest neighbourhood in the US (NRHP district).

Look for historic district neighbourhood swedish

N Clark St around Foster & Balmoral Aves, Andersonville, Chicago

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Edgewater Beach, Chicago — Photo: Alanscottwalker · CC BY-SA 3.0 · Wikimedia Commons (resized)

35 Worth the detour within North Side

Edgewater Beach Apartments

The pink 1928 tower at the end of Lake Shore Drive — the surviving sister of the vanished Edgewater Beach Hotel resort (NRHP).

Look for architecture landmark

N Sheridan Rd at the north end of Lake Shore Drive, Edgewater, Chicago

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View east along Argyle Street from Broadway, West Argyle Street Historic District — Photo: JeremyA · CC BY-SA 3.0 · Wikimedia Commons (resized)

36 Worth the detour within North Side

Argyle Street (Asia on Argyle)

Chicago's 'Little Saigon' — a few blocks of pho houses, bakeries and Asian markets around the Argyle 'L' stop (NRHP historic district; Asia on Argyle night market).

Look for neighbourhood historic district food street

W Argyle St between Broadway and Sheridan Rd, Uptown, Chicago

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37 Worth the detour within North Side

Aragon Ballroom

The 1926 Spanish-palace dance hall with a twinkling-star ceiling, now a rock venue.

Look for music concert ballroom historic

1106 W Lawrence Ave, Chicago, IL 60640

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38 Worth the detour within North Side

Emil Bach House

Frank Lloyd Wright's 1915 cubic Prairie house in Rogers Park — tours via the FLW Trust, and you can even stay overnight.

Look for frank lloyd wright prairie school house

7415 N Sheridan Rd, Chicago, IL 60626

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39 Worth the detour within North Side

Riviera Theatre

Rapp & Rapp's 1917 Balaban & Katz movie palace in the Uptown theatre district, now a rock venue.

Look for music concert theatre historic

4746 N Racine Ave, Chicago, IL 60640

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40 Worth the detour within North Side

Rosehill Cemetery

Chicago's largest cemetery (350 acres), entered through William Boyington's castle-like gate — Victorian monuments and mausoleums.

Look for cemetery historic architecture

5800 N Ravenswood Ave, Chicago, IL 60660

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41 Worth the detour within North Side

The Wieners Circle

Lincoln Park's late-night char-dog stand (to 4am weekends), as famous for the staff's good-natured verbal abuse as for its dogs.

2622 N Clark St, Chicago, IL 60614

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42 Worth the detour within North Side

Half Acre Balmoral

The big Balmoral brewery and taproom (2017) of Half Acre, a staple of Chicago craft brewing since 2006.

2050 W Balmoral Ave, Chicago, IL 60625

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43 Worth the detour within North Side

Carol's Pub

Uptown's late-night honky-tonk — one of Chicago's last straight-up country bars, closed in 2016 and revived in 2018.

4659 N Clark St, Chicago, IL 60640

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44 Worth the detour within North Side

L&L Tavern

Lakeview dive at Clark & Belmont since the 1950s — Irish whiskey selection, a dark lore, and a stop on Anthony Bourdain's The Layover.

3207 N Clark St, Chicago, IL 60657

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45 Worth the detour within North Side · Indian & Pakistani

Hema's Kitchen

Hema Potla's homestyle Indian kitchen on Devon — a Check, Please! and Reader favourite for decades.

2439 W Devon Ave, Chicago, IL 60659

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46 Worth the detour within North Side · Indian & Pakistani

Uru-Swati

All-vegetarian Devon Avenue standby spanning North and South India — dosas, chaat, curries and thalis.

2629 W Devon Ave, Chicago, IL 60659

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47 Worth the detour within North Side

Chicago History Museum

The city's history museum at the south end of Lincoln Park — Lincoln's deathbed, the Great Fire, and an exhibit on the Chicago hot dog.

Look for museum history

1601 N Clark St, Chicago, IL 60614

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48 Worth the detour within North Side

Graceland Cemetery

Victorian garden cemetery (1860) of Chicago's builders — Burnham, Sullivan, Mies, Marshall Field, Roger Ebert — with Lorado Taft's 'Eternal Silence'.

Look for cemetery historic architecture

4001 N Clark St, Chicago, IL 60613

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49 Worth the detour within North Side

Biograph Theater

The 1914 Lincoln Avenue movie house outside which John Dillinger was shot by the FBI in 1934; now Victory Gardens' stage.

Look for theatre historic movie

2433 N Lincoln Ave, Chicago, IL 60614

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50 Worth the detour within North Side

Montrose Point Bird Sanctuary

15 lakefront acres where 300+ migratory species stop at 'the Magic Hedge'. Free.

Look for nature preserve lakefront birding free

Montrose Harbor (W Montrose Ave & Lake Shore Dr), Chicago, IL 60640

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51 Worth the detour within North Side

Swedish American Museum

Andersonville's 1976 museum of Swedish immigrant history and art, with a children's immigration museum upstairs.

Look for museum history family

5211 N Clark St, Chicago, IL 60640

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52 Worth the detour within North Side

The Vic Theatre

The 1912 Victoria vaudeville house in Lakeview, now a concert hall that has hosted Bowie, Pearl Jam and Coldplay.

Look for music concert theatre historic

3145 N Sheffield Ave, Chicago, IL 60657

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53 Worth the detour within North Side

St. Michael's Church (Old Town)

The German parish's Romanesque church rebuilt inside its fire-scarred walls after 1871 — Bavarian Baroque interior and Munich glass.

Look for church architecture historic

1633 N Cleveland Ave, Chicago, IL 60614

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54 Worth the detour within North Side · Pizza

George's Deep Dish

Edgewater carryout doing a focaccia-like sourdough deep dish; on both the Infatuation deep-dish ranking and Time Out's top pizza list.

6221 N Clark St, Chicago, IL 60660

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55 Worth the detour within North Side

Byron's Hot Dogs

Classic Wrigleyville hot-dog stand serving the North Side since 1975 — reviewed by the Infatuation and on Time Out's best-hot-dogs list.

1017 W Irving Park Rd, Chicago, IL 60613

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56 Worth the detour within North Side

Atelier

Intimate Lincoln Square tasting-menu room — one Michelin star.

4835 N Western Ave, Chicago, IL 60625

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57 Worth the detour within North Side · Mexican

Taqueria El Asadero

Cash-only North Center taqueria — 'some of the freshest tacos in town' (Time Out); the Infatuation rates its carne asada 8.1.

2213 W Montrose Ave, Chicago, IL 60618

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58 Worth the detour within North Side

Murphy's Bleachers

Wrigleyville's best-known Cubs bar — a 1930s hot-dog stand (Ernie's, then Ray's Bleachers) facing the bleacher entrance at Sheffield & Waveland.

3655 N Sheffield Ave, Chicago, IL 60613

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59 Worth the detour within North Side

Hai Yen

Long-running Argyle Street Vietnamese dining room prized for consistency — shaking beef, tapioca dumplings, bún bò Huế.

1055 W Argyle St, Chicago, IL 60640

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60 Worth the detour within North Side

Boka

Lee Wolen's Lincoln Park flagship by the Steppenwolf — one Michelin star.

1729 N Halsted St, Chicago, IL 60614

61 Worth the detour within North Side

Esmé

Jenner Tomaska and Katrina Bravo's Lincoln Park 'atelier' restaurant — one Michelin star.

2200 N Clark St, Chicago, IL 60614

62 Worth the detour within North Side

Boonie's Filipino Restaurant

Family-style Filipino restaurant — Michelin Bib Gourmand.

4337 N Western Ave, Chicago, IL 60618

63 Worth the detour within North Side

Sochi Saigonese Kitchen

Modern Vietnamese on Belmont — Michelin Bib Gourmand.

1358 W Belmont Ave, Chicago, IL 60657

64 Worth the detour within North Side · Pizza

Munno Pizzeria & Bistro

Uptown pizzeria-bistro on Clark St — Michelin Bib Gourmand (Chicago 2024).

4656 N Clark St, Chicago, IL 60640

65 Deep cut within North Side

Couch Tomb

The last tomb left from the old City Cemetery under Lincoln Park — Ira Couch's 1858 mausoleum, too heavy to move.

Look for cemetery historic oddities

2045 N Lincoln Park West (in Lincoln Park), Chicago, IL

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66 Deep cut within North Side

Essanay Studios

Where Charlie Chaplin made 'His New Job' and Gloria Swanson started out — the 1907 silent-film studio's terracotta-trimmed home, a Chicago Landmark (now St. Augustine College).

Look for film history landmark

W Argyle St, Uptown, Chicago, IL 60640

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67 Deep cut within North Side

Bryn Mawr Avenue Historic District

Three blocks of 1897–1928 apartment hotels and terracotta façades once home to Chicago's elite — Bryn Mawr & Belle Shore hotels; made a Chicago Landmark district in Sept 2026.

Look for historic district architecture

900–1100 blocks of W Bryn Mawr Ave (Sheridan Rd to Broadway), Edgewater, Chicago

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68 Deep cut within North Side

Francis J. Dewes House

Brewer Francis Dewes's 1896 Lincoln Park mansion — exuberant German Baroque, with caryatids holding up the balcony; a Chicago Landmark beside his brother's matching house.

Look for house architecture landmark

503 W Wrightwood Ave, Chicago, IL 60614

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69 Deep cut within North Side · Italian

Amici-Chicago

Small Buena Park Italian spot that invited TikTok critic Keith Lee (16M followers) — his visit produced a documented 'Keith Lee effect' surge (Fox32).

3933 N Broadway, Chicago, IL 60613

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Closed — kept for the record 70

Uptown Theatre — CLOSED

Rapp & Rapp's 1925 'acre of seats in a magic city' — the largest movie palace ever built in Chicago, shuttered since 1981 and awaiting restoration (exterior only).

Look for theatre architecture historic landmark

4816 N Broadway, Chicago, IL 60640

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Northwest Side 63 places · area 3 of 9

Wicker Park, Bucktown, Ukrainian Village, Logan Square, Humboldt Park, Avondale, Albany Park

1 Must see within Northwest Side

Jibaritos y Más

Yelitza Rivera's Logan Square corner (2016) with the widest jibarito menu in town — lines out the door, now with a sit-down room next door.

3400 W Fullerton Ave, Chicago, IL 60647

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boulevard street view — Photo: Thshriver · CC BY-SA 3.0 · Wikimedia Commons (resized)

2 Must see within Northwest Side

Logan Square Boulevards District

The Northwest Side's grandest stretch of Chicago's boulevard system — graystone 'boulevard of the millionaires' mansions around Logan and Palmer squares (NRHP + Chicago Landmark district).

Look for historic district boulevard architecture

Logan Blvd, Kedzie Blvd & Palmer Sq around Logan Square, Chicago, IL 60647

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3 Must see within Northwest Side

Holy Trinity Orthodox Cathedral

Louis Sullivan's only intact house of worship (1903), a Russian-village church in Ukrainian Village, part-funded by Tsar Nicholas II.

Look for cathedral church architecture sullivan landmark

1121 N Leavitt St, Chicago, IL 60622

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4 Must see within Northwest Side

Humboldt Park

Jens Jensen's 207-acre park — the Prairie School boathouse and swan boats on the lagoon, and the 1895 stables now housing the National Museum of Puerto Rican Arts & Culture. Free.

Look for park lagoon boat free

1400 N Sacramento Ave, Chicago, IL 60622

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5 Must see within Northwest Side

Basilica of St. Hyacinth

Avondale's 1917 Polish 'cathedral' — a papal basilica since 2003 and the heart of Chicago's Polish Village.

Look for church basilica architecture

3636 W Wolfram St, Chicago, IL 60618

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6 Must see within Northwest Side

Empty Bottle

Ukrainian Village's storefront indie-rock club — cheap shows, free Mondays, a bar cat and the midwinter Music Frozen Dancing fest.

Look for music club concert

1035 N Western Ave, Chicago, IL 60622

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7 Must see within Northwest Side

The Hideout

A century-old frame house tucked into an industrial corridor (once bootleggers' turf) — beloved for concerts, variety shows and comedy.

Look for music bar concert hidden gem

1354 W Wabansia Ave, Chicago, IL 60642

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8 Must see within Northwest Side

Superdawg Drive-In

The 1948 carhop drive-in under the two giant hot-dog mascots on the roof — on both the Infatuation and Time Out best-hot-dog lists.

6363 N Milwaukee Ave, Chicago, IL 60646

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9 Must see within Northwest Side

Roeser's Bakery

Humboldt Park bakery run by the same family since 1911 — custom cakes, strudel, coffee cake and paczki.

3216 W North Ave, Chicago, IL 60647

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10 Must see within Northwest Side · Italian

Daisies

Joe Frillman's farm-driven Logan Square pasta restaurant (own 30-acre farm) — Michelin Bib Gourmand and Green Star.

2375 N Milwaukee Ave, Chicago, IL 60647

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11 Must see within Northwest Side

Kasia's Deli

Ukrainian Village deli at Chicago Ave & Hoyne opened in 1982 by Polish immigrant Kazimiera 'Kasia' Bober, whose award-winning pierogi reached United flights and presidents.

2101 W Chicago Ave, Chicago, IL 60622

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12 Must see within Northwest Side

Longman & Eagle

The 'Eat Sleep Whisky' gastropub-inn that put Logan Square on the dining map (Condé Nast Traveler); Michelin-listed in 2024.

2657 N Kedzie Ave, Chicago, IL 60647

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13 Must see within Northwest Side

The 606 (Bloomingdale Trail)

The 2.7-mile elevated rail-trail through Logan Square, Humboldt Park, Wicker Park and Bucktown. Free.

Look for trail park free

1805 N Ridgeway Ave, Chicago, IL 60647

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14 Must see within Northwest Side · Pizza

Pizz'amici

Tiny West Town pizzeria in a former barbershop from veteran Chicago pizza makers — #3 on Time Out's citywide ranking, #1 on Chowhound's tavern list and an Esquire Best New Restaurant 2025.

1215 W Grand Ave, Chicago, IL 60642

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15 Must see within Northwest Side

Margie's Candies

Ice-cream parlor and candy shop at Armitage & Western since 1921 — the Infatuation's old-school list and Chicago Magazine's Iconic Eats (hot fudge sundae).

1960 N Western Ave, Chicago, IL 60647

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16 Must see within Northwest Side

Kasama

Ukrainian Village Filipino bakery-by-day, tasting-menu-by-night — raised to two Michelin stars in 2025.

1001 N Winchester Ave, Chicago, IL 60622

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17 Must see within Northwest Side

Lula Cafe

Logan Square's pioneering farm-to-table café (since 1999) — Michelin Bib Gourmand and on Eater Chicago's 38 essential restaurants.

2537 N Kedzie Blvd, Chicago, IL 60647

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18 Must see within Northwest Side · Mexican

Mi Tocaya Antojería

Diana Dávila's Logan Square antojería — Michelin Bib Gourmand and one of Eater Chicago's 38 essential restaurants.

2800 W Logan Blvd, Chicago, IL 60647

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19 Must see within Northwest Side

Smoque BBQ

Old Irving Park's benchmark barbecue — Michelin Bib Gourmand and one of Eater Chicago's 38 essential restaurants.

3800 N Pulaski Rd, Chicago, IL 60641

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20 Must see within Northwest Side · Indian & Pakistani

Superkhana International

Logan Square Indian restaurant — Michelin Bib Gourmand and Eater Chicago 38.

3059 W Diversey Ave, Chicago, IL 60647

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21 Must see within Northwest Side

Rainbo Club

Ukrainian Village dive since 1935 — Nelson Algren's haunt, famous neon sign and photo booth.

1150 N Damen Ave, Chicago, IL 60622

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22 Must see within Northwest Side

Tryzub Ukrainian Kitchen

Ukrainian Village's Old-World Ukrainian kitchen (opened 2016) — the Infatuation's pick for a varenyky-and-vodka night.

2201 W Chicago Ave, Chicago, IL 60622

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23 Must see within Northwest Side · Japanese

Akahoshi Ramen

Logan Square ramen counter from Mike Satinover — Reddit's 'Ramen Lord' of r/ramen — on Bon Appétit's 20 best new restaurants of 2024 and the NYT's 25 best in Chicago.

2340 N California Ave, Unit B, Chicago, IL 60647

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24 Must see within Northwest Side

Café Colao

Puerto Rican-owned bakery-café on Paseo Boricua a block from Humboldt Park — some of the city's best Puerto Rican coffee and pastries.

2638 W Division St, Chicago, IL 60622

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25 Must see within Northwest Side

Giant

Logan Square's tiny, always-full New American — Michelin Bib Gourmand (Chicago 2024).

3209 W Armitage Ave, Chicago, IL 60647

26 Worth the detour within Northwest Side

Bohemian National Cemetery

Freethinkers' cemetery founded 1877 by Czech immigrants — Bohemian-art monuments, Mayor Anton Cermak's grave and the Eastland-disaster victims; CAC-toured.

Look for cemetery history art

5255 N Pulaski Rd, Chicago, IL 60630

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27 Worth the detour within Northwest Side

Copernicus Center (Gateway Theatre)

Rapp & Rapp's 1930 Gateway movie palace, restored as the Polish-American Copernicus cultural centre — concerts and dance most nights; next door to the Taste of Polonia festival.

Look for theatre polish culture landmark

5216 W Lawrence Ave, Chicago, IL 60630

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28 Worth the detour within Northwest Side

Intuit Art Museum

America's leading museum of outsider and self-taught art — home of the recreated Henry Darger Room; reopened in 2025 after a major expansion.

Look for museum art outsider

756 N Milwaukee Ave, Chicago, IL 60642

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29 Worth the detour within Northwest Side

St. Nicholas Ukrainian Catholic Cathedral

1915 Neo-Byzantine cathedral modelled on Kyiv's St. Sophia — its thirteen copper domes crown Ukrainian Village; interior mosaics are among Chicago's finest.

Look for church cathedral landmark

Ukrainian Village, Chicago, IL 60622 (street number pending re-verify)

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30 Worth the detour within Northwest Side

National Museum of Puerto Rican Arts and Culture

The only US national museum devoted to Puerto Rican art, in Humboldt Park's 1895 stables — the park's oldest building.

Look for museum art culture

Humboldt Park (1895 park stables), Chicago, IL 60622

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Northwest Tower Chicago — Photo: Zagalejo · CC BY-SA 3.0 · Wikimedia Commons (resized)

31 Worth the detour within Northwest Side

The Robey (Northwest Tower)

The triangular 1929 Art Deco Northwest Tower — first skyscraper of its size outside downtown — at the six-way Milwaukee/North/Damen crossing, now a hotel with skyline rooftop bars.

Look for architecture art deco hotel rooftop

Milwaukee / North / Damen six-way intersection, Wicker Park, Chicago

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32 Worth the detour within Northwest Side

St. Stanislaus Kostka Church

Mother church of Chicago Polonia (1867–81, Patrick Keely) — by 1897 the largest parish in the US; a 'Polish Cathedral' landmark in Noble Square.

Look for church polish landmark

1327 N Noble St, Chicago, IL 60642

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Wicker Park Historic District 2 — Photo: Thshriver · CC BY-SA 3.0 · Wikimedia Commons (resized)

33 Worth the detour within Northwest Side

Wicker Park District

Victorian mansions of 'Beer Baron Row' (Hoyne) and Pierce Ave lining the 1870 park — one of the city's best post-Fire residential streetscapes (Chicago Landmark district).

Look for historic district architecture mansions

Pierce Ave & Hoyne Ave around Wicker Park, Chicago, IL 60622

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Illinois Centennial Memorial Column — Photo: Loganresident · CC BY 2.5 · Wikimedia Commons (resized)

34 Worth the detour within Northwest Side

Illinois Centennial Monument

The eagle-topped column at the heart of Logan Square (1918), by Henry Bacon of the Lincoln Memorial — the hub of the boulevard system.

Look for monument landmark free

3100 W Logan Blvd (Logan Square), Chicago, IL 60647

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35 Worth the detour within Northwest Side

Chef Darnell Reed's Southern kitchen built on his great-grandmother's recipes — in the Michelin Guide and on Eater Chicago's 38. Left Lincoln Square in Oct 2024; reopened Aug 2025 in Albany Park as a breakfast/brunch spot (Wed–Sun).

4114 N Kedzie Ave, Chicago, IL 60618

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36 Worth the detour within Northwest Side · Mexican

Big Star

Paul Kahan's honky-tonk taco and whiskey bar at the Damen-Milwaukee crossroads of Wicker Park, with its packed summer patio.

1531 N Damen Ave, Chicago, IL 60622

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37 Worth the detour within Northwest Side · Pizza

Paulie Gee's Logan Square

Derrick Tung's Logan Square outpost of the Brooklyn pizzeria — his Detroit-style square won the 2018 U.S. Pizza Cup; a fixture of Time Out's essential-pizza list.

2451 N Milwaukee Ave, Chicago, IL 60647

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38 Worth the detour within Northwest Side

Polish Museum of America

One of the oldest and largest ethnic museums in the US (1935), in the old Polish Downtown.

Look for museum history

984 N Milwaukee Ave, Chicago, IL 60642

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39 Worth the detour within Northwest Side

Ukrainian National Museum

Ukrainian Village museum of folk art, pysanky (Easter eggs) and immigrant history.

Look for museum history

2249 W Superior St, Chicago, IL 60612

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40 Worth the detour within Northwest Side

St. Mary of the Angels

Bucktown's block-long Polish Renaissance church (1920) modelled on St. Peter's, its dome ringed by angels.

Look for church architecture

1850 N Hermitage Ave, Chicago, IL 60622

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41 Worth the detour within Northwest Side · Pizza

Middle Brow Bungalow

Logan Square brewpub-bakery; on Time Out's top-pizza ranking and the only brewpub on Chowhound's tavern-pizza list.

2840 W Armitage Ave, Chicago, IL 60647

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42 Worth the detour within Northwest Side

Redhot Ranch (Bucktown)

Cheap, late Depression-dog stand on Armitage — on both the Infatuation and Time Out hot-dog lists.

2449 W Armitage Ave, Chicago, IL 60647

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43 Worth the detour within Northwest Side

Feld

Chicago's newest one-star in the 2025 Michelin guide, which also gave it a Green Star for sustainable practice.

2018 W Chicago Ave, Chicago, IL 60622

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44 Worth the detour within Northwest Side · Indian & Pakistani

Mirra

Zubair Mohajir and Rishi Kumar's colorful Indian-Mexican Bucktown restaurant — new Michelin Bib Gourmand 2025.

1954 W Armitage Ave, Chicago, IL 60622

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45 Worth the detour within Northwest Side

Irazu

Bucktown's family-run Costa Rican restaurant — casados, gallo pinto, oatmeal shakes; 'extremely affordable and incredibly good' (Infatuation).

1865 N Milwaukee Ave, Chicago, IL 60647

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46 Worth the detour within Northwest Side

Taxim

Wicker Park's modern Greek — no Greektown kitsch, refined regional cooking.

1558 N Milwaukee Ave, Chicago, IL 60622

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47 Worth the detour within Northwest Side

The Map Room

Bucktown's 'travelers' tavern' since 1992 — maps on the walls, a beer list you can't fit another bottle on.

1949 N Hoyne Ave, Chicago, IL 60647

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48 Worth the detour within Northwest Side

Schwa

Wicker Park's punk tasting counter — no servers, loud rap, wild cooking; one Michelin star.

1466 N Ashland Ave, Chicago, IL 60622

49 Worth the detour within Northwest Side

Cellar Door Provisions

Logan Square bakery-restaurant — Michelin Bib Gourmand.

3025 W Diversey Ave, Chicago, IL 60647

50 Worth the detour within Northwest Side · Italian

Tortello Pastificio

Pasta shop and restaurant — Michelin Bib Gourmand in 2024 and 2025.

1746 W Division St, Chicago, IL 60622

51 Worth the detour within Northwest Side · Mexican

Bloom Plant Based Kitchen

All-plant kitchen named a Michelin Bib Gourmand (Chicago 2024).

1559 N Milwaukee Ave, Chicago, IL 60622

52 Worth the detour within Northwest Side

Lardon

Logan Square salumeria/café — Michelin Bib Gourmand (Chicago 2024).

2200 N California Ave, Chicago, IL 60647

53 Worth the detour within Northwest Side

Mama Delia

Spanish restaurant on Michelin's 2024 Chicago Bib Gourmand list.

1721 W Division St, Chicago, IL 60622

54 Worth the detour within Northwest Side · Korean

Mott St

Wicker Park/Noble Square Asian-American small-plates spot — Michelin Bib Gourmand (Chicago 2024).

1401 N Ashland Ave, Chicago, IL 60622

55 Worth the detour within Northwest Side · Korean

Perilla

River West Korean-American restaurant (401 N Milwaukee) on Michelin's 2024 Chicago Bib Gourmand list.

401 N Milwaukee Ave, Chicago, IL 60654

56 Worth the detour within Northwest Side

Pompette

French café-bar — Michelin Bib Gourmand (Chicago 2024).

1960 N Damen Ave, Chicago, IL 60647

57 Worth the detour within Northwest Side

Andros Taverna

Greek taverna just off Logan Square Park — in the Michelin Guide.

2542 N Milwaukee Ave, Chicago, IL 60647

58 Worth the detour within Northwest Side · Mexican

Dove's Luncheonette

Wicker Park retro luncheonette (One Off Hospitality) — in the Michelin Guide.

1545 N Damen Ave, Chicago, IL 60622

59 Worth the detour within Northwest Side · Chinese

Chef's Special Cocktail Bar

Bucktown Chinese-American cocktail bar with a Michelin Bib Gourmand.

2165 N Western Ave, Chicago, IL 60647

60 Deep cut within Northwest Side

Villa District

Seven boulevard blocks of 126 Prairie & Craftsman bungalows (1907–25) with double lots and deep setbacks — a hidden NRHP + Chicago Landmark district.

Look for historic district bungalows architecture

Irving Park — blocks around Avers & Hamlin Aves north of Addison St, Chicago

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61 Deep cut within Northwest Side

Ukrainian Village District

Chicago Landmark district of worker cottages and two-flats around the onion-domed churches — the heart of the city's Ukrainian community (CAC walking tour).

Look for historic district neighbourhood

Ukrainian Village, Chicago (Chicago Landmark district)

By , ,

62 Deep cut within Northwest Side

Polish Triangle (Polonia Triangle)

The plaza at the heart of old 'Polish Downtown', where nearly every major Polish-American organisation once had its headquarters — summer 'Tuesdays at the Triangle' events.

Look for plaza history polish

Division St / Milwaukee Ave / Ashland Ave, Wicker Park–Noble Square, Chicago

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Closed — kept for the record 63

Parachute — CLOSED

Beverly Kim and Johnny Clark's highly personal Korean-American restaurant in Avondale — one of the most creative rooms in town — CLOSED 23 Mar 2024 after 10 years (Michelin star 2014–21, James Beard 2019); the space is now the chefs' casual Parachute HiFi music bar.

3500 N Elston Ave, Chicago, IL 60618

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West Side 40 places · area 4 of 9

Pilsen, Little Village, Little Italy & Taylor St, Garfield Park, Austin

1 Must see within West Side

Al's #1 Italian Beef

The Taylor Street original (1938) where the family claims the Italian beef was invented; the beef for every Al's is still roasted here. #1 on the Infatuation's Italian-beef ranking and a fixture of every Chicago beef list.

1079 W Taylor St, Chicago, IL 60607

By , , +1,

2 Must see within West Side

MacArthur's Restaurant

Austin's soul-food cafeteria (1997) of Mississippi-born MacArthur Alexander — a West Side institution whose regulars included Barack Obama.

5412 W Madison St, Chicago, IL 60644

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3 Must see within West Side

Site of the Great Chicago Fire (Pillar of Fire)

Where the 1871 fire began in the O'Leary barn — now, fittingly, the CFD's Quinn Fire Academy, with Egon Weiner's bronze 'Pillar of Fire' and a plaque marking the spot (Chicago Landmark).

Look for history landmark sculpture

558 W DeKoven St, Chicago, IL 60607

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Hull House building — Photo: Yvphotos · CC BY-SA 3.0 · Wikimedia Commons (resized)

4 Must see within West Side

Jane Addams Hull-House Museum

The two surviving buildings of Jane Addams's 1889 settlement house on the UIC campus — the birthplace of American social work. Free (suggested donation).

Look for museum historic house free

800 S Halsted St, Chicago, IL 60607

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Our Lady of Sorrows 080202 — Photo: JeremyA · CC BY-SA 3.0 · Wikimedia Commons (resized)

5 Must see within West Side

Our Lady of Sorrows Basilica

Garfield Park's 1902 Renaissance Revival basilica with a gold-leafed barrel vault — one of three papal basilicas in Chicago (WTTW's 'Most Beautiful Places').

Look for church basilica architecture

3121 W Jackson Blvd, Chicago, IL 60612

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6 Must see within West Side

United Center

Home of the Bulls and Blackhawks; the 'Spirit' Michael Jordan statue stands in the atrium by Gate 4.

Look for arena sport bulls

1901 W Madison St, Chicago, IL 60612

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7 Must see within West Side

Goose Island Fulton Street Taproom

The taproom attached to Goose Island's production brewery (brewing here since 1995) — test batches and Bourbon County Stout rarities.

1800 W Fulton St, Chicago, IL 60612

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8 Must see within West Side · Mexican

Carnitas Uruapan

The Carbajal family's Pilsen carnitas house since 1975, 'arguably the most famous taqueria in Chicago'; the original is a carry-out counter.

1725 W 18th St, Chicago, IL 60608

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9 Must see within West Side · Mexican

Don Pedro Carnitas

Pilsen carnitas house opened by Pedro Duarte in 1981 — pork cooked in its own fat, sold by weight; weekend lines out the door.

1113 W 18th St, Chicago, IL 60608

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10 Must see within West Side · Pizza

Home Run Inn (original, 31st Street)

The 1923 Little Village tavern (named for baseballs through its window) where Home Run Inn pizza began in 1947 — the brand that founded National Tavern-Style Pizza Day.

4254 W 31st St, Chicago, IL 60623

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11 Must see within West Side · Mexican

Asian Cuisine Express

Little Village's unlikely al pastor champion — a Chinese-Thai takeout counter whose trompo makes some of the best al pastor in Chicago.

3823 W 31st St, Chicago, IL 60623

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12 Must see within West Side

Carm's Beef and Italian Ice

University Village corner stand (since 1929) — the Infatuation calls its jus the best in Chicago; cash-only ice counter next door.

1057 W Polk St, Chicago, IL 60607

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13 Must see within West Side · Coffee & cafés

Cafe Jumping Bean

One of Pilsen's first coffeehouse-galleries (1994), opened by Eleazar Delgado in an old barber shop at 18th & Bishop — a neighbourhood living room for artists.

1439 W 18th St, Chicago, IL 60608

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14 Must see within West Side

Garfield Park Conservatory

Jens Jensen's 1908 'landscape art under glass' — one of the largest conservatories in the US, with free admission.

Look for conservatory garden free

300 N Central Park Ave, Chicago, IL 60624

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15 Must see within West Side

National Museum of Mexican Art

Pilsen's free museum of Mexican art — one of the largest Latinx cultural institutions in the US (10,000+ works); its Día de Muertos show is a city ritual.

Look for museum art free

1852 W 19th St, Chicago, IL 60608

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16 Must see within West Side

Thalia Hall

Pilsen's 1892 hall modelled on the Prague opera house, now one of the city's favourite music venues (with Dusek's downstairs).

Look for music concert theatre historic

1807 S Allport St, Chicago, IL 60608

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park waterfall landscape — Photo: MrHarman · CC BY-SA 3.0 · Wikimedia Commons (resized)

17 Must see within West Side

Columbus Park

Jens Jensen's own favourite work (1915–20) in Austin — a prairie river, council rings and stone waterfalls interpreting the Illinois landscape. Free.

Look for park landscape free

500 S Central Ave, Chicago, IL 60644

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18 Must see within West Side · Mexican

La Chaparrita

Little Village grocery-counter taquería widely ranked among Chicago's very best tacos.

2500 S Whipple St, Chicago, IL 60623

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19 Must see within West Side

Mario's Italian Lemonade

Taylor Street summer-only Italian-ice stand since 1954 — one of Chicago Magazine's 50 Iconic Eats.

1068 W Taylor St, Chicago, IL 60607

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20 Must see within West Side · Italian

Tufano's Vernon Park Tap

Little Italy tavern founded 1930 by Joseph and Teresa DiBuono — James Beard America's Classics Award (2008).

1073 W Vernon Park Pl, Chicago, IL 60607

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21 Must see within West Side · Mexican

Mariscos San Pedro

Mexican seafood house tucked into Thalia Hall from the Obelix / Taqueria Chingón team — whole fish from a wood-burning oven with tortillas and salsas.

1227 W 18th St, Chicago, IL 60608

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22 Must see within West Side

Pleasant House Pub

Pilsen pub famous for its royal pies — Michelin Bib Gourmand (Chicago 2024).

2119 S Halsted St, Chicago, IL 60608

23 Worth the detour within West Side

Garfield Park Fieldhouse (Gold Dome)

The 1928 Spanish Baroque 'Gold Dome' fieldhouse, a gold-leafed Chicago Landmark towering over Garfield Park — under a $9M restoration.

Look for landmark building park

300 N Central Park Ave, Chicago, IL

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24 Worth the detour within West Side

Austin Town Hall

1929 town hall at the heart of Austin — now a Chicago Park District cultural centre and fieldhouse with a historic auditorium.

Look for landmark park cultural center

5610 W Lake St, Chicago, IL 60644

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25 Worth the detour within West Side

Simone's

Pilsen's Green-Restaurant-certified bar and cultural space — solar panels, salvaged fittings, a bar made from a bowling lane.

960 W 18th St, Chicago, IL 60608

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26 Worth the detour within West Side

HaiSous Vietnamese Kitchen

Chef Thai Dang's 'unapologetically authentic' Vietnamese dining room in Pilsen — a James Beard-semifinalist kitchen and neighbourhood mainstay.

1800 S Carpenter St, Chicago, IL 60608

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27 Worth the detour within West Side · Mexican

Panadería Nuevo León

Pilsen's beloved ~50-year-old panadería — trays of conchas, cookies and fruit empanadas; its Three Kings roscas made the Sun-Times in 2026.

1634 W 18th St, Chicago, IL 60608

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28 Worth the detour within West Side

Chez Joël Bistro

French bistro hidden off the Taylor Street bustle — a locals' and critics' favourite with the neighbourhood's best patio and a deep wine list.

1119 W Taylor St, Chicago, IL 60607

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29 Worth the detour within West Side

Soulé (North Lawndale)

Chef Bridgette Flagg's soul-food restaurant — North Lawndale's first full-service sit-down restaurant in 50 years.

3615 W Roosevelt Rd, Chicago, IL 60624

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30 Worth the detour within West Side

Pilsen Historic District

National Register district of 1870s–1910s Bohemian worker cottages, storefronts and churches — now the heart of Mexican Pilsen and its murals along 16th and 18th Streets.

Look for historic district mural

Lower West Side (Pilsen), around 18th St, Chicago (per Wikipedia / City of Chicago landmark district)

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31 Worth the detour within West Side

Maxwell Street Market

The Sunday open-air flea market descended from the 1880s Maxwell Street bazaar — tools, tires, produce and some of the city's best street tacos.

Look for market street food

800 S Desplaines St, Chicago, IL 60607

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32 Worth the detour within West Side

Notre Dame de Chicago

The domed 1892 French-Romanesque church of the city's old French parish, in Little Italy/University Village.

Look for church architecture historic

1335 W Harrison St, Chicago, IL 60607

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33 Worth the detour within West Side

Holy Family Church

The 1860 Gothic Revival church that survived the Great Fire (the O'Learys were parishioners) — the second-oldest Catholic church in Chicago.

Look for church architecture historic

1080 W Roosevelt Rd, Chicago, IL 60608

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34 Worth the detour within West Side

EL Ideas

Phillip Foss's freewheeling Douglas Park tasting menu where diners wander into the open kitchen — in the Michelin Guide.

2419 W 14th St, Chicago, IL 60608

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35 Worth the detour within West Side · Mexican

5 Rabanitos

Casual, affordable Pilsen BYOB from chef Alfonso Sotelo (ex-Bayless) — Michelin-listed regional Mexican cooking.

1758 W 18th St, Chicago, IL 60608

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36 Worth the detour within West Side · Mexican

Birrieria Reyes de Ocotlan

Pilsen birrieria with a half-dozen-item menu — Time Out: 'one visit to this one before you stop caring about the rest.'

1322 W 18th St, Chicago, IL 60608

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37 Worth the detour within West Side · Mexican

Lucido's Tacos

Little Village taqueria that grew from Adan Lucido's home pop-up — al pastor carved to order off the spit with pineapple and salsa.

4147 W 26th St, Chicago, IL

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38 Worth the detour within West Side · Italian

Ferrara Bakery

Little Italy bakery founded 1908 on Taylor St by Salvatore Ferrara (of the candy family), now run by the third generation.

2210 W Taylor St, Chicago, IL 60612

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39 Worth the detour within West Side

Ghin Khao

Low-key Pilsen restaurant for Northern Thai fare — Michelin Bib Gourmand.

2128 W Cermak Rd, Chicago, IL 60608

40 Deep cut within West Side

Jackson Boulevard District

A block of 1880s Victorian rowhouses and mansions that survived the West Side's decline — a Chicago Landmark district and NRHP listing.

Look for historic district architecture

W Jackson Blvd between Laflin St and Ashland Ave, Near West Side, Chicago

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South Side 51 places · area 5 of 9

Chinatown, Bridgeport, Bronzeville, Hyde Park, Woodlawn, South Shore

park landscape, quarry pond — Photo: Warren LeMay from Chicago, IL, United States · CC BY-SA 4.0 · Wikimedia Commons (resized)

1 Must see within South Side

Palmisano Park

A 1830s limestone quarry turned 27-acre park — a fishing pond in the pit, terraced wetlands and the city's best skyline hill.

Look for park

2700 S Halsted St area (former Stearns Quarry), Bridgeport, Chicago (per Wikipedia)

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2 Must see within South Side

Obama Presidential Center

The presidential museum, library branch and tower in Jackson Park, opened Juneteenth (June 19) 2026 — timed tickets sold out months ahead.

Look for museum library landmark

1401 E 60th St (Jackson Park), Chicago, IL 60637

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3 Must see within South Side

Valois Restaurant

Hyde Park cafeteria since 1921, one of the oldest in the US — Barack Obama's regular, his orders still on the board. Cash only.

1518 E 53rd St, Chicago, IL 60615

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4 Must see within South Side

Pearl's Place

Bronzeville soul-food dining room since 1993 — Roadfood rates it 'Excellent / Worth a Detour'.

3901 S Michigan Ave, Chicago, IL 60653

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5 Must see within South Side · Korean

Maria's Packaged Goods & Community Bar (Kimski)

Bridgeport's community bar run by the Marszewski family (Maria, from Busan) — with Kimski, the Korean-Polish kitchen added in 2016.

960 W 31st St, Chicago, IL 60608

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6 Must see within South Side

Cleo's Southern Cuisine

Chef Kristen Harper's Creole-leaning Bronzeville soul-food counter — some of Chicago's best wings and fried chicken; Keith Lee's only 10/10 on his 2023 Chicago tour.

4248 S Cottage Grove Ave, Chicago, IL

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7 Must see within South Side

Roberts Temple Church of God in Christ

Bronzeville church where Mamie Till-Mobley held her son Emmett Till's open-casket funeral in 1955 — part of the Emmett Till and Mamie Till-Mobley National Monument (2023).

Look for church historic memorial

4021 S State St, Chicago, IL

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8 Must see within South Side

S. R. Crown Hall

Mies van der Rohe's 1956 glass-and-steel architecture school at IIT — widely held to be his finest work; a National Historic Landmark.

Look for architecture building landmark

3360 S State St, Chicago, IL 60616

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9 Must see within South Side

Rate Field

The White Sox's 1991 ballpark across 35th Street from old Comiskey, with the exploding scoreboard and fireworks after every Sox homer.

Look for ballpark stadium white sox sport

333 W 35th St, Chicago, IL 60616

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Aquarium-Style Smoker — Photo: Southern Foodways Alliance · CC BY 2.0 · Wikimedia Commons (resized)

10 Must see within South Side

Lem's Bar-B-Q

Founded 1954 by the Lemons brothers and still family-run; South Side aquarium-smoker rib tips. 2025 James Beard America's Classics award. James Beard America's Classics Award, 2025.

311 E 75th St, Chicago, IL 60619

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11 Must see within South Side · Italian

Ricobene's

Bridgeport Italian institution since 1946 whose 1976 breaded steak sandwich Bourdain featured on Parts Unknown.

252 W 26th St, Chicago, IL 60616

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12 Must see within South Side · Pizza

Phil's Pizza

Bridgeport's tavern-style institution since 1960 — greasy, generously topped thin pies cut in squares, counter service, cash only.

1102 W 35th St, Chicago, IL 60609

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13 Must see within South Side · African & Ethiopian

Yassa African Restaurant

Senegalese family restaurant (2004, Bronzeville since 2015) — called one of the city's best African restaurants; South Side Weekly's 'Best Resurrection' after a fire.

3511 S King Dr, Chicago, IL 60653

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14 Must see within South Side

Honey 1 BBQ

Chicago-style aquarium-smoker barbecue, in Bronzeville since 2015 — a Choose Chicago South Side pick. Cash only.

746 E 43rd St, Chicago, IL 60653

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15 Must see within South Side

Daley's Restaurant

Chicago's oldest restaurant — a Woodlawn lunch counter opened in 1892 for World's Fair builders; Muhammad Ali ate here between workouts. Moved across 63rd to Woodlawn Station in 2019.

6257 S Cottage Grove Ave, Chicago, IL 60637

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16 Must see within South Side

Daisy's Po'Boy & Tavern

James Beard winner Erick Williams' Louisiana tavern (2022) a block from his Virtue — live New Orleans jazz on first Wednesdays.

5215 S Harper Ave, Chicago, IL 60615

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17 Must see within South Side

Museum of Science and Industry

The largest science centre in the Western Hemisphere, in the 1893 World's Fair Palace of Fine Arts — U-505 submarine, coal mine, Pioneer Zephyr.

Look for museum science family

5700 S DuSable Lake Shore Dr, Chicago, IL 60637

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18 Must see within South Side

Frederick C. Robie House

Frank Lloyd Wright's 1910 Prairie School masterpiece in Hyde Park, inscribed by UNESCO in The 20th-Century Architecture of Frank Lloyd Wright. Tours by the FLW Trust.

Look for frank lloyd wright prairie school house

5757 S Woodlawn Ave, Chicago, IL 60637

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19 Must see within South Side

DuSable Black History Museum

Founded 1961 in Washington Park — the oldest independent African American museum in the country.

Look for museum history

740 E 56th Pl, Chicago, IL 60637

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20 Must see within South Side

Garden of the Phoenix

The Japanese garden on Jackson Park's Wooded Island, rooted in Japan's 1893 World's Fair pavilion; 160 cherry trees in spring. Free.

Look for garden park free

6401 S Stony Island Ave (Wooded Island, Jackson Park), Chicago, IL 60637

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museum building exterior — Photo: Warren LeMay from Chicago, IL, United States · CC BY-SA 2.0 · Wikimedia Commons (resized)

21 Must see within South Side

Institute for the Study of Ancient Cultures Museum

The University of Chicago's free museum of the ancient Near East (ex-Oriental Institute) — the 40-ton Khorsabad lamassu, Egypt, Persia, Mesopotamia.

Look for museum free

1155 E 58th St, Chicago, IL 60637

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22 Must see within South Side

Promontory Point

Alfred Caldwell's limestone-stepped peninsula with a castle-like field house — a downtown-skyline view, swimming off the rocks and fire pits. Free.

Look for park lakefront skyline view free

5491 S DuSable Lake Shore Dr, Chicago, IL 60615

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23 Must see within South Side

Stony Island Arts Bank

Theaster Gates's restored 1923 bank — the Johnson Publishing library, Frankie Knuckles' records, galleries and free events.

Look for gallery arts library house music free

6760 S Stony Island Ave, Chicago, IL 60649

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24 Must see within South Side

The Duck Inn

Bridgeport gastropub — a Michelin Bib Gourmand in both the 2024 and 2025 Chicago lists.

2701 S Eleanor St, Chicago, IL 60608

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25 Must see within South Side

Virtue

Chef Erick Williams's Hyde Park Southern restaurant within view of the University of Chicago — Michelin Bib Gourmand 2025; Eater Chicago 38.

1462 E 53rd St, Chicago, IL 60615

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26 Must see within South Side · Chinese

Qing Xiang Yuan Dumplings

Chinatown's dumpling specialist, risen from a Richland Center basement stand — ~40 fillings in three cooking styles, more varieties than anywhere in Chicago.

2002 S Wentworth Ave, Chicago, IL 60616

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27 Must see within South Side · Chinese

JM Seafood

Bridgeport Cantonese seafood house from the Wing Yip family — live-tank shellfish and wok-fried lobster over lap-cheong sticky rice.

3312 S Halsted St, Chicago, IL 60608

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28 Worth the detour within South Side

Quinn Chapel A.M.E. Church

Home of Chicago's oldest Black congregation (1844), an Underground Railroad station; its 1892 sanctuary still stands at Bronzeville's northern edge (Chicago Landmark).

Look for church black history landmark

S Wabash Ave, Bronzeville (Near South Side), Chicago

By , , +1,

29 Worth the detour within South Side

Ebenezer Missionary Baptist Church

Birthplace of gospel music — Thomas A. Dorsey's 1931 choir here launched Mahalia Jackson and a new American sound (Chicago Landmark 2011).

Look for church music history landmark

Bronzeville, Chicago, IL 60653

By , , +1,

30 Worth the detour within South Side

Bronzeville Winery

Black-owned wine bar-restaurant from the Silver Room's owner — art-hung room, DJs and live music, a list that champions minority-owned producers.

S Cottage Grove Ave at E 44th St, Bronzeville, Chicago, IL 60653

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31 Worth the detour within South Side

Pui Tak Center

The 1928 On Leong Merchants Association building — pagoda towers, green tile roofs and terracotta, Chinatown's signature landmark (Chicago Landmark 1993).

Look for architecture landmark chinatown

S Wentworth Ave, Chinatown, Chicago, IL 60616

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32 Worth the detour within South Side

Rockefeller Memorial Chapel

The University of Chicago's soaring Gothic chapel, with a 72-bell carillon among the largest instruments ever built.

Look for church chapel architecture

5850 S Woodlawn Ave, Chicago, IL 60637

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33 Worth the detour within South Side

Ida B. Wells-Barnett House

The 1889 Romanesque house where Ida B. Wells lived 1919–30 — a National Historic Landmark (private; view from the street).

Look for house historic landmark

3624 S Dr Martin Luther King Jr Dr, Chicago, IL 60653

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34 Worth the detour within South Side

Pilgrim Baptist Church (ruins)

Adler & Sullivan's 1890 synagogue turned the church where Thomas Dorsey's choir gave birth to gospel music; burned in 2006, its stone walls still stand (a gospel museum is planned).

Look for church historic ruins music sullivan

3301 S Indiana Ave, Chicago, IL 60616

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35 Worth the detour within South Side

Washington Park

Olmsted & Vaux's 372-acre South Side park, home of Lorado Taft's 'Fountain of Time' and the DuSable museum.

Look for park

Washington Park community area, Chicago (per Wikipedia)

By ,

36 Worth the detour within South Side

South Shore Cultural Center

The 1906 South Shore Country Club, now a Park District cultural center with a beach, nature sanctuary and golf — the Obamas held their wedding reception here.

Look for cultural center park beach

7059 S South Shore Dr, Chicago, IL 60649

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37 Worth the detour within South Side

Fountain of Time

Lorado Taft's 1922 concrete procession of 100 figures passing before Father Time, at the west end of the Midway. Free.

Look for sculpture public art park free

Washington Park, 5900 S Cottage Grove Ave, Chicago, IL 60637

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38 Worth the detour within South Side

Victory Monument

Bronzeville's 1928 memorial to the Black 8th Illinois regiment (370th Infantry) of WWI, won by a Chicago Defender campaign.

Look for monument memorial historic free

3500 S Dr Martin Luther King Jr Dr, Chicago, IL 60653

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39 Worth the detour within South Side

Ping Tom Memorial Park

Chinatown's riverside park on an old rail yard — pagoda pavilion, kayak launch and the water-taxi stop. Free.

Look for park river free

1700 S Wentworth Ave, Chicago, IL 60616

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40 Worth the detour within South Side

Chinese American Museum of Chicago

Small Chinatown museum on the Chinese journey to the Midwest, in the old Quong Yick warehouse.

Look for museum history

238 W 23rd St, Chicago, IL 60616

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41 Worth the detour within South Side

Chicago Bee Building

Anthony Overton's 1929–31 Art Deco terracotta newspaper building in Bronzeville, now the Chicago Bee branch library.

Look for architecture art deco library historic

3647 S State St, Chicago, IL 60609

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42 Worth the detour within South Side

Smart Museum of Art

The University of Chicago's always-free art museum in Edward Larrabee Barnes's limestone buildings.

Look for museum art free

5550 S Greenwood Ave, Chicago, IL 60637

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43 Worth the detour within South Side

Heller House

Frank Lloyd Wright's 1897 Isidore Heller house in Hyde Park, a step toward the Prairie style (private; view from the street).

Look for frank lloyd wright prairie school house

5132 S Woodlawn Ave, Chicago, IL 60615

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44 Worth the detour within South Side · Chinese

Lao Sze Chuan

Tony Hu's original Chinatown Sichuan house, through a side gate off Archer.

2172 S Archer Ave, Chicago, IL 60616

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45 Worth the detour within South Side · Chinese

Chi Cafe

Chinatown's Hong Kong-style café for the late-night crowd — open till 4am most nights, 24 hours on weekends.

2160 S Archer Ave, Chicago, IL 60616

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46 Worth the detour within South Side · Chinese

Hing Kee Restaurant

Chinatown's soup-dumpling specialist — xiaolongbao made fresh daily in full view of the dining room.

2140 S Archer Ave, Chicago, IL 60616

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47 Worth the detour within South Side · Chinese

Han 202

Bridgeport's bargain Chinese tasting menu — four inventive courses for well under $40.

605 W 31st St, Chicago, IL 60616

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48 Worth the detour within South Side · Pizza

Nella Pizza e Pasta

Hyde Park Neapolitan pizzeria on 55th St — Michelin Bib Gourmand (Chicago 2024).

1125 E 55th St, Chicago, IL 60615

49 Worth the detour within South Side · Chinese

Yao Yao

Sichuan restaurant — Michelin Bib Gourmand 2024 and 2025.

230 W Cermak Rd, Chicago, IL 60616

50 Worth the detour within South Side · Chinese

Dolo

Sleek Chinatown restaurant with a full bar — Michelin-listed; 'diners would do well to try the impressive specialty menu'.

2222 S Archer Ave, Chicago, IL 60616

51 Deep cut within South Side

Medici on 57th

The 'Med' — UChicago's hangout since 1963, booths carved with students' poetry and political rants; a breakfast-to-late menu.

1327 E 57th St, Chicago, IL 60637

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Southwest Side 19 places · area 6 of 9

Back of the Yards, McKinley Park, Brighton Park, Archer Heights, Marquette Park, Midway

1 Must see within Southwest Side · Pizza

Vito & Nick's Pizzeria

Ashburn's tavern-pizza shrine since the 1940s — #1 on Time Out's citywide pizza ranking ('the king of tavern-style') and the spot with the most 'best' nods in Chowhound's tavern-pizza research.

8433 S Pulaski Rd, Chicago, IL 60652

By , , +2, ,

2 Must see within Southwest Side · Mexican

Xocome Antojeria

Family-run Archer Heights counter where scratch masa is the star — tlacoyos, picaditas, sopes and giant quesadillas (Infatuation 9.4).

5200 S Archer Ave, Unit 8, Chicago, IL 60632

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3 Must see within Southwest Side

Marz Community Brewing Co.

McKinley Park warehouse taproom from the Maria's/Kimski family — wraparound bar, brewhouse views, arcade, karaoke and comedy nights.

3630 S Iron St, Chicago, IL 60609

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4 Must see within Southwest Side · Mexican

La Internacional (Back of the Yards taqueria)

The early-'80s supermercado whose back-of-store taco stand became a destination — the original Paco's Tacos operation.

4556 S Ashland Ave, Chicago, IL 60609

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stone stockyard gate, 2008 — Photo: Zol87 from Chicago, Illinois, USA · CC BY-SA 2.0 · Wikimedia Commons (resized)

5 Must see within Southwest Side

Union Stock Yard Gate

The 1879 Burnham & Root limestone gate — all that remains of the 475-acre Union Stock Yards that made Chicago 'hog butcher for the world'. A National Historic Landmark; free.

Look for landmark monument historic free

850 W Exchange Ave, Chicago, IL 60609

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6 Must see within Southwest Side

Marquette Park & MLK Living Memorial

Where Martin Luther King Jr. marched for open housing in 1966 (and was struck by a rock); the Living Memorial's three pillars at Marquette Rd & Kedzie tell the Fair Housing story. Free.

Look for park memorial historic free

6700 S Kedzie Ave, Chicago, IL 60629

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7 Must see within Southwest Side · Mexican

Birrieria Zaragoza

Family-run Archer Heights birrieria devoted to Jalisco-style roasted goat. Michelin Bib Gourmand; birria on Chicago Magazine's Iconic Eats. (TEMPORARILY CLOSED as of Oct 2026 per Michelin/Apple listings — check before going.)

4852 S Pulaski Rd, Chicago, IL 60632

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8 Must see within Southwest Side

Tony's Italian Beef

South Siders' pick for the city's best beef — one of the biggest sandwiches in town, thicker slices that stay tender (Infatuation 8.0).

7007 S Pulaski Rd, Chicago, IL 60629

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9 Must see within Southwest Side

Weber's Bakery

Family bakery since 1930 (founded at 45th & Kedzie) — the Garfield Ridge institution of German/Polish/Scandinavian-rooted sweets; named Illinois' best bakery.

7055 W Archer Ave, Chicago, IL 60638

By ,

10 Must see within Southwest Side · Mexican

Paco's Tacos (Archer original)

Brighton Park taqueria spun out of Paco Francisco's La Internacional taco stand — about 3,000 tacos a day, voted among the city's best.

4311 S Archer Ave, Chicago, IL 60632

By ,

11 Worth the detour within Southwest Side

Holy Cross Church (Back of the Yards)

National Register Lithuanian church (1915) whose twin towers rise over Back of the Yards, the old stockyards neighbourhood.

Look for church historic

1740 W 46th St, Chicago, IL

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12 Worth the detour within Southwest Side

Balzekas Museum of Lithuanian Culture

The only museum in North America devoted to Lithuanian history and culture — in the city with the most Lithuanians outside Lithuania.

Look for museum history

6500 S Pulaski Rd, Chicago, IL 60629

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13 Worth the detour within Southwest Side

McKinley Park

The 71-acre 1901 park named for the assassinated president — lagoon, trails and an outdoor ice rink. Free.

Look for park lagoon free

2210 W Pershing Rd, Chicago, IL 60609

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14 Worth the detour within Southwest Side

Huck Finn Donuts

Archer Avenue's 24-hour donut-and-diner counter, on Time Out's list of old-school Chicago doughnut shops.

3414 S Archer Ave, Chicago, IL 60608

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15 Worth the detour within Southwest Side

Sherman Park

Olmsted Brothers & Burnham 'neighbourhood park' (1905) ringed by a lagoon, with a Burnham-designed fieldhouse — a landmark of the South Parks reform movement.

Look for park lagoon

New City / Back of the Yards, Chicago (per Wikipedia)

By ,

16 Worth the detour within Southwest Side

Pticek & Son Bakery

Family-run European bakery founded 1943, one of the Garfield Ridge Polish bakeries that survived — a Paczki Day pilgrimage.

5523 S Narragansett Ave, Chicago, IL 60638

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17 Worth the detour within Southwest Side · Mexican

Taquerías Atotonilco (Gage Park)

One of the city's oldest taquerias (founded 1972 by Don Jesús from Arandas, Jalisco), cash-only and open till 3–4am on weekends.

5656 S Kedzie Ave, Chicago, IL 60629

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18 Deep cut within Southwest Side

Davis Square Park

One of the first 1905 South Parks small parks, built to give stockyards families a fieldhouse, baths and playgrounds.

Look for park historic

Back of the Yards, Chicago (per Wikipedia)

By , ,

19 Deep cut within Southwest Side

Bubbly Creek

The stockyards' notorious waste channel — Upton Sinclair's 'Bubbly Creek' still burps methane from century-old sediment, now ringed by new trails.

Look for river oddities

South Fork of the South Branch, Chicago River (headwaters, per Wikipedia)

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Far South 16 places · area 7 of 9

Pullman, Beverly & Morgan Park, Chatham, Roseland, the Calumet

1 Must see within Far South

Calumet Fisheries

Smokehouse shack by the 95th Street bridge on the Calumet River since 1948, wood-smoking fish on site. A James Beard America's Classics honoree.

3259 E 95th St, Chicago, IL 60617

By , ,

2 Must see within Far South

Top-Notch Beefburger

Beverly's wood-panelled burger shop since 1942 — fresh-ground round on a feather-light bun, fries cooked in beef tallow.

2116 W 95th St, Chicago, IL 60643

By , ,

3 Must see within Far South

Horse Thief Hollow

Beverly's award-winning brewpub (2013) — a 6,000 sq ft Western Avenue taproom with house beer and Southern-leaning food.

10426 S Western Ave, Chicago, IL 60643

By , ,

4 Must see within Far South

Lexington Betty Smokehouse

Pullman smokehouse of Dominique Leach, 2023 'Master of 'Cue' on Food Network's BBQ Brawl — one of the city's best barbecue spots.

756 E 111th St, Chicago, IL 60628

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5 Must see within Far South

Sanders BBQ Supply Co.

Beverly's Texas-style smokehouse — on the New York Times' 2025 list of the 50 best US restaurants and Jean Banchet Best Counter Service 2026.

1742 W 99th St, Chicago, IL 60643

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Pullman Administration Building & clock tower (park centrepiece) — Photo: Historic American Buildings Survey, creator · Public domain · loc.gov · Documentation compiled after 1933 · Library of Congress

6 Must see within Far South

Pullman National Historical Park

George Pullman's 1880s company town — the clock-tower factory, Hotel Florence and rowhouses; site of the 1894 strike and the Pullman porters' story. NPS unit since 2015.

Look for national park historic district pullman

11141 S Cottage Grove Ave, Chicago, IL 60628

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7 Must see within Far South

National A. Philip Randolph Pullman Porter Museum

Museum of the Pullman porters and the Brotherhood of Sleeping Car Porters — the birthplace of Black labor history, within Pullman National Historical Park.

Look for museum historic

10406 S Maryland Ave, Chicago, IL

By ,

8 Must see within Far South

Ridge Historic District (Beverly)

One of the largest urban districts on the National Register — 3,000+ homes on the glacial ridge of Beverly and Morgan Park by Wright, Maher, Griffin, Burnham and Shaw; walk Longwood Drive past the Givins 'Irish castle'. Free.

Look for historic district architecture house frank lloyd wright prairie school free

Longwood Dr & W 103rd St (Beverly), Chicago, IL 60643

By ,

9 Must see within Far South

The Original Rainbow Cone

Beverly's pink stand serving its five-flavour sliced cone since 1926 — a South Side institution (Choose Chicago) and one of Chicago Magazine's 50 Iconic Eats.

9233 S Western Ave, Chicago, IL 60643

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10 Must see within Far South

Dat Donut

Chatham's round-the-clock donut shop — its glazed made the Daily Meal's America's 25 best; often called the best donuts on the South Side.

8249 S Cottage Grove Ave, Chicago, IL 60619

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Calumet Park fieldhouse, Chicago — Photo: Zol87 from Chicago, IL, USA · CC BY-SA 4.0 · Wikimedia Commons (resized)

11 Worth the detour within Far South

Calumet Park & Beach

181-acre East Side lakefront park with a sandy beach, a 1924 Classical Revival fieldhouse (Chicago Landmark) and a model-train exhibit; views to the Indiana steel shore.

Look for park beach landmark

9801 S Avenue G, Chicago, IL 60617

By , , +1,

12 Worth the detour within Far South

Walter Burley Griffin Place District

A street of Prairie School houses (1909–14), seven by Walter Burley Griffin — later the designer of Canberra — a Chicago Landmark district.

Look for prairie school historic district house

1600–1800 blocks of W 104th Pl (Griffin Place), Beverly, Chicago

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13 Worth the detour within Far South

Givins Beverly Castle (Beverly Unitarian Church)

An 1886 limestone 'Irish castle' on the Beverly ridge, built by developer Robert Givins for his bride — home of Beverly Unitarian Church since 1941.

Look for architecture landmark castle

10244 S Longwood Dr, Chicago, IL 60643

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14 Worth the detour within Far South

Janson's Drive-In

Beverly's neon-trimmed 1960 drive-in, revived in 2014 with its classic décor and menu intact — featured on Chicago's Best.

9900 S Western Ave, Chicago, IL 60643

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15 Worth the detour within Far South

Wolf Lake (William W. Powers State Recreation Area)

The 800-acre lake straddling the Illinois–Indiana line in Hegewisch — otters, beavers, swans and fishing amid the old steel landscape. Free.

Look for nature lake state park free

12949 S Avenue O, Chicago, IL 60633

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16 Deep cut within Far South

Greenstone Church (Pullman)

Pullman's 1882 serpentine-greenstone church, designed by Solon S. Beman as part of the model town.

Look for church historic

11211 S St Lawrence Ave, Chicago, IL

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Suburbs & North Shore 38 places · area 8 of 9

Evanston, Oak Park, Skokie, Wilmette, Glencoe, Berwyn, the western suburbs

1 Must see within Suburbs & North Shore

Riverside (Olmsted planned village)

Olmsted & Vaux's 1869 curving-street suburb along the Des Plaines River — one of America's first planned communities, a National Historic Landmark (expanded 2023).

Look for historic district landscape olmsted

Village of Riverside, IL 60546

By , , +1,

2 Must see within Suburbs & North Shore

Frank Lloyd Wright Historic District (Oak Park)

The world's largest concentration of Wright buildings — two dozen Prairie houses within walking distance of his Home & Studio; FLW Trust guided walks April–November.

Look for frank lloyd wright architecture historic district

Oak Park, IL 60302 (historic district)

By , , +1,

3 Must see within Suburbs & North Shore · Italian

Freddy's Pizza

Cicero corner grocery turned Italian deli-pizzeria, run by Neapolitan immigrant Joe Quercia since 1973 — hot-table Italian, pizza and some of the area's best gelato.

1600 S 61st Ave, Cicero, IL 60804

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4 Must see within Suburbs & North Shore

Hecky's Barbecue

Evanston barbecue institution of the late Hecky Powell — the North Shore's rib-tip and sauce benchmark (Axios rib-tip Food Fight).

1902 Green Bay Rd, Evanston, IL

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5 Must see within Suburbs & North Shore

Walker Bros. Original Pancake House (Wilmette)

The 1960 Wilmette original of the North Shore pancake family (in Ordinary People) — Zagat's 'best breakfast, bar none'.

153 Green Bay Rd, Wilmette, IL 60091

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6 Must see within Suburbs & North Shore

FitzGerald's Nightclub

Berwyn roots-music club and tavern (FitzGerald family since 1980, a music hall since the 1930s) — in 2025 the first Illinois music venue on the National Register.

6615 Roosevelt Rd, Berwyn, IL 60402

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7 Must see within Suburbs & North Shore

Unity Temple

Frank Lloyd Wright's 1908 poured-concrete temple in Oak Park — part of UNESCO's 20th-Century Architecture of Frank Lloyd Wright inscription.

Look for frank lloyd wright temple architecture

875 Lake St, Oak Park, IL 60301

By ,

8 Must see within Suburbs & North Shore

Frank Lloyd Wright Home and Studio

Where Wright lived and worked 1889–1909 and developed the Prairie style; a National Historic Landmark, toured by the Frank Lloyd Wright Trust.

Look for frank lloyd wright prairie school house

951 Chicago Ave, Oak Park, IL 60302

By ,

9 Must see within Suburbs & North Shore

Baháʼí House of Worship

The lace-domed 1953 Baháʼí temple on the Wilmette lakefront — the oldest surviving Baháʼí House of Worship in the world, with formal gardens.

Look for temple architecture gardens free

100 Linden Ave, Wilmette, IL 60091

By ,

10 Must see within Suburbs & North Shore

Chicago Botanic Garden

385 acres on nine islands in the Cook County Forest Preserves at Glencoe — 24 gardens, prairies and greenhouses; the winter Orchid Show.

Look for botanic garden park

1000 Lake Cook Rd, Glencoe, IL 60022

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11 Must see within Suburbs & North Shore

Brookfield Zoo

The 216-acre Chicago Zoological Park in Brookfield — polar bears, the Seven Seas dolphins, Tropic World.

Look for zoo family

8400 31st St, Brookfield, IL 60513

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12 Must see within Suburbs & North Shore

Ravinia Festival

North America's oldest outdoor music festival — the Chicago Symphony's summer home; picnic on the lawn.

Look for music festival concert park pavilion

418 Sheridan Rd, Highland Park, IL 60035

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arboretum landscape in winter — Photo: Patrick Pelletier · CC BY-SA 3.0 · Wikimedia Commons (resized)

13 Must see within Suburbs & North Shore

Morton Arboretum

1,700 acres of trees in Lisle with 16 miles of trails and a children's garden; Illumination in winter.

Look for arboretum garden park trail

4100 IL-53, Lisle, IL 60532

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14 Must see within Suburbs & North Shore

Illinois Holocaust Museum and Education Center

Stanley Tigerman's Skokie museum founded by survivors, with its pioneering interactive survivor-hologram theatre.

Look for museum history

9603 Woods Dr, Skokie, IL 60077

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15 Must see within Suburbs & North Shore

Johnnie's Beef

Elmwood Park walk-up open since 1961 — Steve Dolinsky's (ABC7 Hungry Hound) #1 Italian beef in the suburbs, with an 'ambrosial' jus, and the lemon ice that closes every order.

7500 W North Ave, Elmwood Park, IL 60707

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Gene and Judes Hot Dog — Photo: ErikTheRedder · CC BY 3.0 · Wikimedia Commons (resized)

16 Must see within Suburbs & North Shore

Gene & Jude's

River Grove stand (1946; here since 1950) — no seats, no ketchup; the gold standard of the Depression dog on both the Infatuation and Time Out hot-dog lists.

2720 N River Rd, River Grove, IL 60171

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17 Must see within Suburbs & North Shore · Pizza

Lou Malnati's Pizzeria (Lincolnwood)

The 1971 original of Lou Malnati's — where the family's buttercrust deep dish began, before it became Chicago's best-known deep-dish name.

6649 N Lincoln Ave, Lincolnwood, IL 60712

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18 Worth the detour within Suburbs & North Shore

Autre Monde Café & Spirits

Berwyn's Mediterranean café from fine-dining alumni — a past Michelin Bib Gourmand and on the Tribune critic's top-50 Chicago restaurants (2018).

6727 Roosevelt Rd, Berwyn, IL 60402

By , , +1,

19 Worth the detour within Suburbs & North Shore

Charles Gates Dawes House

Château-style 1894 lakefront mansion of Nobel laureate and US Vice President Charles G. Dawes — a National Historic Landmark run by the Evanston History Center.

Look for house historic landmark

Evanston lakefront, IL (per NPS NHL record)

By , ,

20 Worth the detour within Suburbs & North Shore

Avery Coonley House (Frank Lloyd Wright)

Wright's own 'most successful of my houses' (1906–09) — a long, low U-shaped Prairie complex set into Olmsted's Riverside; National Historic Landmark (private, exterior view).

Look for frank lloyd wright architecture house

Riverside, IL 60546 (private residence)

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exterior of the Ward W. Willits House — Photo: James Steakley · CC BY-SA 3.0 · Wikimedia Commons (resized)

21 Worth the detour within Suburbs & North Shore

Ward W. Willits House (Frank Lloyd Wright)

Widely considered Wright's first mature Prairie-style house (1901–02), on Highland Park's Sheridan Road — a National Historic Landmark (private, exterior view).

Look for frank lloyd wright architecture house

1445 Sheridan Rd, Highland Park, IL 60035

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22 Worth the detour within Suburbs & North Shore

Block Museum of Art (Northwestern)

Northwestern's free art museum on the lakefill campus — prints, photography, film and ambitious exhibitions.

Look for museum art free

40 Arts Circle Dr, Evanston, IL 60208

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23 Worth the detour within Suburbs & North Shore

Grosse Point Lighthouse

Evanston's 1873 lighthouse on the lake bluff, a National Historic Landmark; summer weekend tours.

Look for lighthouse lakefront historic landmark

2601 Sheridan Rd, Evanston, IL 60201

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24 Worth the detour within Suburbs & North Shore

Arthur Heurtley House

Frank Lloyd Wright's 1902 Prairie-style house on Forest Avenue — low roman-brick walls and a raised main floor, a National Historic Landmark.

Look for frank lloyd wright prairie school house

Forest Ave, Oak Park, IL (per Wikipedia)

By ,

25 Worth the detour within Suburbs & North Shore

Burr Oak Cemetery

Historic African American cemetery — resting place of Emmett Till, Dinah Washington and Willie Dixon.

Look for cemetery historic memorial

Alsip, IL (per Wikipedia)

By ,

26 Worth the detour within Suburbs & North Shore

Cantigny Park

Col. Robert McCormick's 500-acre Wheaton estate — gardens, his mansion, and the First Division tank museum.

Look for park garden museum

1S151 Winfield Rd, Wheaton, IL 60189

By ,

Hemingway Birthplace (Queen Anne house, 1890), Oak Park — Photo: MauraWen · CC BY-SA 4.0 · Wikimedia Commons (resized)

27 Worth the detour within Suburbs & North Shore

Ernest Hemingway Birthplace

The Queen Anne house where Hemingway was born in 1899, restored as a museum.

Look for house museum historic

339 N Oak Park Ave, Oak Park, IL 60302

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Haymarket Martyr's Memorial — Photo: Zol87 from Chicago, IL, USA · CC BY-SA 3.0 · Wikimedia Commons (resized)

28 Worth the detour within Suburbs & North Shore

Haymarket Martyrs' Monument

The 1893 monument over the graves of the executed Haymarket anarchists — a pilgrimage site for May Day; surrounded by 'Radical Row'. National Historic Landmark.

Look for monument cemetery memorial historic

Forest Home Cemetery, 863 S Des Plaines Ave, Forest Park, IL 60130

By ,

29 Worth the detour within Suburbs & North Shore

Fermilab

The national particle-physics lab on the prairie — a bison herd since 1967, Wilson Hall and mathematical sculptures; grounds free with photo ID.

Look for science prairie free oddity

Kirk Rd & Pine St, Batavia, IL 60510

By ,

30 Worth the detour within Suburbs & North Shore

Pleasant Home

George W. Maher's 1897 John Farson House — an early Prairie-style mansion and National Historic Landmark, open for tours.

Look for house prairie school museum landmark

217 S Home Ave, Oak Park, IL 60302

By ,

31 Worth the detour within Suburbs & North Shore

Naper Settlement

Living-history village of 30 historic buildings and costumed interpreters telling a 19th-century Illinois town's story.

Look for museum historic village family

523 S Webster St, Naperville, IL 60540

By ,

32 Worth the detour within Suburbs & North Shore

Kaufman's Bagel & Delicatessen

Skokie deli opened in the 1960s as a hub for Holocaust survivors — one of Chicagoland's oldest Jewish delis; bagel and lox on Chicago Magazine's 50 Iconic Eats.

4905 Dempster St, Skokie, IL 60077

By ,

33 Worth the detour within Suburbs & North Shore

Russell's Barbecue

Opened 1930 — the oldest continuously operating barbecue restaurant in the Chicago area, on Thatcher Avenue since the 1940s.

1621 N Thatcher Ave, Elmwood Park, IL 60707

By ,

34 Worth the detour within Suburbs & North Shore

Hackney's on Harms

The 1939 original of the North Shore burger tavern — burgers on house dark rye from a 1920s back-porch recipe.

1241 Harms Rd, Glenview, IL 60025

By ,

35 Worth the detour within Suburbs & North Shore

Bennison's Bakery

Evanston's European-style bakery since 1938 — ~700 customers a day for strudel, Danish and Fat Tuesday pączki.

1000 Davis St, Evanston, IL

By ,

Oak Park Il Conservatory1 — Photo: IvoShandor · CC BY 2.5 · Wikimedia Commons (resized)

36 Deep cut within Suburbs & North Shore

Oak Park Conservatory

1929 glasshouse with 20,000 plants in Mediterranean, tropical and desert rooms — a free hidden gem south of downtown Oak Park.

Look for conservatory garden

615 Garfield St, Oak Park, IL 60304

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37 Deep cut within Suburbs & North Shore

One Lake Brewing

Brewpub in the 1920 First National Bank of Oak Park — original dentil mouldings, award-winning pilsner and stouts.

1 Lake St, Oak Park, IL 60302

By ,

38 Deep cut within Suburbs & North Shore

Joy Yee Noodles (Evanston)

The Joy Yee mini-empire's 1993 original — a sunny downtown corner of pan-Asian noodles and Evanston's favourite bubble tea.

533 Davis St, Evanston, IL 60201

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Day Trips 17 places · area 9 of 9

Indiana Dunes, Starved Rock, Milwaukee, the Lake Michigan shore

1 Must see within Day Trips

SC Johnson Administration Building

Frank Lloyd Wright's 1939 'dendriform'-columned Great Workroom and Research Tower in Racine — free tours by reservation.

Look for frank lloyd wright architecture building

1525 Howe St, Racine, WI 53403

By , ,

2 Must see within Day Trips

Kopp's Frozen Custard (Greenfield)

Milwaukee-area custard stand since 1950 — one of the city's 'big three' with Gilles and Leon's; the Greenfield store is the original HQ.

7631 W Layton Ave, Greenfield, WI 53220

By , ,

3 Must see within Day Trips

Frank's Diner (Kenosha)

One of America's oldest continuously operating lunch-car diners (1926), hauled to Kenosha by six horses — on the National Register.

downtown Kenosha, WI (per Wikipedia)

By , ,

4 Must see within Day Trips

Solly's Grille

Glendale diner (1936) thought to have created the Wisconsin butter burger.

4629 N Port Washington Rd, Glendale, WI 53212

By , ,

5 Must see within Day Trips

Indiana Dunes National Park

15 miles of Lake Michigan beaches and towering dunes an hour from the Loop by the South Shore Line — Mount Baldy, the West Beach dune trails.

Look for national park dunes beach trail

1215 N State Road 49, Porter, IN 46304

By ,

6 Must see within Day Trips

Starved Rock State Park

Sandstone canyons and seasonal waterfalls on the Illinois River, 90 minutes south-west of Chicago — Illinois's most-visited state park.

Look for state park canyons trail waterfalls

2668 E 875th Rd, Oglesby, IL 61348

By ,

Quadracci Pavilion exterior — Photo: Bmzuckerman · CC BY 4.0 · Wikimedia Commons (resized)

7 Must see within Day Trips

Milwaukee Art Museum

Calatrava's lakefront Quadracci Pavilion whose Burke Brise Soleil 'wings' open and close daily — 90 minutes north of Chicago.

Look for museum art architecture lakefront

700 N Art Museum Dr, Milwaukee, WI 53202

By ,

8 Must see within Day Trips

Milwaukee Public Market

Third Ward food hall of ~20 vendors — brats, squeaky cheese curds, seafood, Thai — named one of America's best public markets by Frommer's.

Look for market food hall

400 N Water St, Milwaukee, WI 53202

By ,

dune / view from summit — Photo: Indianadunes · CC BY-SA 4.0 · Wikimedia Commons (resized)

9 Must see within Day Trips

Mount Baldy

The 120-ft living dune at the east end of Indiana Dunes National Park — the largest moving dune on Indiana's shore (summit by ranger-led hike).

Look for dunes beach national park trail

Mt. Baldy Beach, US-12, Michigan City, IN 46360

By ,

10 Must see within Day Trips

Leon's Frozen Custard

Milwaukee's neon-lit custard stand since the 1940s — said to have inspired Arnold's on Happy Days.

3131 S 27th St, Milwaukee, WI 53215

By ,

11 Worth the detour within Day Trips

Yerkes Observatory

The 1897 'birthplace of modern astrophysics' on Geneva Lake — home of the world's largest refracting telescope; tours.

Look for observatory historic

373 W Geneva St, Williams Bay, WI 53191

By , ,

12 Worth the detour within Day Trips

Harley-Davidson Museum

The only Harley-Davidson Museum in the world — 450+ motorcycles on a 20-acre Menomonee Valley campus.

Look for museum

400 W Canal St, Milwaukee, WI 53201

By ,

13 Worth the detour within Day Trips

Lakefront Brewery

Riverside craft brewery (1987) that helped revive Milwaukee brewing — its comic tour and Friday fish fry are city rituals.

Look for brewery tour

1872 N Commerce St, Milwaukee, WI 53212

By ,

14 Worth the detour within Day Trips

Pabst Mansion

Captain Frederick Pabst's 1892 Flemish Renaissance Revival mansion, restored and open for tours.

Look for mansion house museum historic

2000 W Wisconsin Ave, Milwaukee, WI 53233

By ,

15 Worth the detour within Day Trips

Discovery World

Lakeshore science-and-technology museum with the Reiman Aquarium and a tall ship.

Look for museum science aquarium family lakefront

500 N Harbor Dr, Milwaukee, WI 53202

By ,

16 Worth the detour within Day Trips

Old Lighthouse Museum

The 1858 Michigan City lighthouse, now a museum in Washington Park by the beach and harbour.

Look for lighthouse museum lakefront historic

1 Heisman Harbor Rd (Washington Park), Michigan City, IN 46360

By ,

17 Worth the detour within Day Trips

Matthiessen State Park

Starved Rock's quieter neighbour — canyon dells and waterfalls about two hours from Chicago.

Look for state park canyons trail waterfalls

2500 IL-178, Oglesby, IL 61348

By ,

How we choose

Named sources recommend every place; review sites never do. Each is pinned to its door and status-checked. Closed places stay, marked closed.

Must see: The places to plan a visit around, graded within each area.
Worth the detour: Strong picks, worth going out of your way for.
Deep cut: For the curious: smaller, odder, more local.

Within each area: by tier, then by named sources, never by popularity. We don’t add ratings, prices or opening hours of our own.

Follow changes — an RSS feed of every closure and status check in this guide.

About this guide

412 places in 9 areas, each recommended by at least two independent sources (89 in all) or one institution such as Michelin.

Every place was checked open and pinned between 3 Oct and 3 Oct 2026. Closed places stay, marked closed.

Photos for 164 places; the rest show a designed cover.

How we choose → Insights →

208 sights and 204 places to eat from the Loop out through the North, West and South Sides to the suburbs and the Indiana Dunes, each traceable to the source that named it. The architecture — the Rookery, Robie House, the river and the lakefront — anchors the map; the food runs on what Chicago does that nowhere else does: deep-dish and tavern-cut thin crust, Italian beef, the dragged-through-the-garden hot dog and the Maxwell Street Polish, the jibarito, mild-sauce chicken, the Rainbow Cone, and the immigrant corridors of Pilsen, Chinatown, Devon Avenue, Argyle and Little Village.

The Loop & Downtown 98 places · area 1 of 9

North Side 70 places · area 2 of 9

Northwest Side 63 places · area 3 of 9

West Side 40 places · area 4 of 9

South Side 51 places · area 5 of 9

Southwest Side 19 places · area 6 of 9

Far South 16 places · area 7 of 9

Suburbs & North Shore 38 places · area 8 of 9

Day Trips 17 places · area 9 of 9

How we choose

Keep Chicago offline

How this guide was made

How the cuisine filters were policed

Web-searched, merit-measured and fact-checked