Chicago

Best Things to Do in Chicago — The Windy City's Greatest Attractions

Chicago rewards exploration with world-class architecture, deep-dish pizza, blues and jazz clubs, stunning lakefront parks, and some of America's finest museums and cultural institutions.

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01
Chicago Riverwalk and Architecture Boat Tour

Chicago Riverwalk and Architecture Boat Tour

Chicago Architecture Center boat tours narrated by architectural docents along the Chicago River reveal America's greatest collection of 20th century buildings — an essential 90-minute exploration of architectural history.

Rising·Score +25
02
Wrigley Field (Cubs Baseball)

Wrigley Field (Cubs Baseball)

Built in 1914, Wrigley Field is America's second-oldest baseball park — watching a Cubs game in this ivy-covered brick outfield landmark under afternoon sunshine is a quintessentially American sporting experience.

Steady·Score +13
03
Chicago's Magnificent Mile

Chicago's Magnificent Mile

Michigan Avenue's luxury shopping corridor between the Chicago River and Oak Street Beach features flagship stores, the Tribune Tower, Water Tower Place, and some of America's most impressive urban streetscapes.

Steady·Score +12
04
Second City Comedy Club

Second City Comedy Club

The legendary improv comedy institution that launched Bill Murray, Tina Fey, Stephen Colbert, Amy Poehler, and dozens of SNL legends — live shows at the original Wells Street location remain essential Chicago culture.

Steady·Score +9
05
Millennium Park and Cloud Gate (The Bean)

Millennium Park and Cloud Gate (The Bean)

Anish Kapoor's Cloud Gate sculpture reflecting the Chicago skyline in its distorted surface has become America's most photographed public artwork — Millennium Park surrounds it with gardens, concerts, and the Pritzker Pavilion.

Steady·Score +8
06
Deep-Dish Pizza at Lou Malnati's

Deep-Dish Pizza at Lou Malnati's

Chicago's defining culinary contribution — the deep-dish pizza with a buttery crust, chunky tomato sauce applied on top of cheese and toppings is polarizing but undeniably iconic. Giordano's and Pequod's are also essential.

Steady·Score +8
07
The Chicago Blues Scene

The Chicago Blues Scene

Visit Buddy Guy's Legends, Kingston Mines, or Rosa's Lounge to experience authentic Chicago electric blues — the music genre born in Mississippi but electrified and urbanized in Chicago's South and West Side clubs.

Steady·Score +8
08
Navy Pier and Lake Michigan Shoreline

Navy Pier and Lake Michigan Shoreline

Chicago's famous lakefront offers 18 miles of accessible waterfront — Navy Pier's Ferris wheel and festival grounds, North Avenue Beach volleyball, and the Chicago Riverwalk create a summer city playground.

Steady·Score +6
09
Chicago's Diverse Neighborhood Food Tour

Chicago's Diverse Neighborhood Food Tour

Pilsen's Mexican murals and tacos, Chinatown's dim sum, Devon Avenue's Indian restaurants, and Andersonville's Swedish bakeries show Chicago as America's most diverse and delicious city for neighborhood food exploration.

Steady·Score +5
10
The Art Institute of Chicago

The Art Institute of Chicago

One of the world's great art museums with Seurat's Sunday on La Grande Jatte, Grant Wood's American Gothic, Edward Hopper's Nighthawks, and thousands of masterworks across all periods and cultures.

Steady·Score +4
11
Museum of Science and Industry

Museum of Science and Industry

America's largest science museum in Jackson Park features the only German U-boat submarine captured in WWII, a full-size coal mine, IMAX films, and hundreds of interactive exhibits for all ages.

Steady·Score +3
12
The Skydeck at Willis Tower (Sears Tower)

The Skydeck at Willis Tower (Sears Tower)

Chicago's tallest building at 1,451 feet features glass-floor Ledge pods extending beyond the building's facade — 103 floors up, you stand over thin air with panoramic views extending across four states.

Steady·Score +3
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Chicago Riverwalk and Architecture Boat Tour

Currently ranked #1. Where will it be in 7 days?