101 Things to Do in Chicago

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Chicago dazzles with soaring architecture, a spectacular lakefront, world-class museums and legendary deep-dish pizza and blues. Browse and book top-rated tours below, or request free quotes from a Chicago travel specialist.

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Welcome to 101 Things to Do in Chicago. Click any activity below to search and book every tour, attraction and experience in Chicago.

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Popular Attractions & Tourist Sites in Chicago

1. Millennium Park — A downtown park home to Anish Kapoor's mirror-polished 'Cloud Gate' sculpture, nicknamed 'The Bean.'

2. Willis Tower Skydeck — The 103rd-floor observation deck with glass-floored 'Ledge' boxes projecting out over the city 1,353 feet below.

3. Navy Pier — A 3,300-foot lakefront pier with the Centennial Ferris Wheel, boat cruises, restaurants and fireworks in summer.

4. Art Institute of Chicago — One of America's oldest and largest art museums, holding Grant Wood's 'American Gothic' and a superb Impressionist collection.

5. Field Museum — A landmark natural history museum whose star exhibit is 'Sue,' the largest and most complete T. rex ever found.

6. Shedd Aquarium — A lakefront aquarium with more than 32,000 animals, from beluga whales to sharks in the Wild Reef.

7. Magnificent Mile — A prestigious stretch of Michigan Avenue lined with flagship stores, hotels and the historic Water Tower.

8. Wrigley Field — The ivy-walled 1914 ballpark of the Chicago Cubs, one of the oldest stadiums in Major League Baseball.

9. Museum of Science and Industry — The largest science museum in the Western Hemisphere, featuring a U-505 German submarine and a walk-through heart.

10. 360 Chicago — An observation deck atop the former John Hancock Center with 'TILT,' a platform that leans you out over the street.

Unique Chicago Experiences

Glide past skyscrapers on an architecture river cruise
Snap a selfie in the reflection of Cloud Gate
Devour a deep-dish pizza in the Loop
Catch live blues on a Chicago club crawl
Bike or stroll the 18-mile Lakefront Trail
Step onto the glass Ledge at the Willis Tower Skydeck
Explore the murals and taquerias of Pilsen
Ride the elevated 'L' train around the downtown Loop
Kayak the Chicago River for skyline views
Cheer the Cubs at ivy-clad Wrigley Field

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Chicago Travel — Frequently Asked Questions

What are the top things to do in Chicago?

Top experiences include Millennium Park, Willis Tower Skydeck, Navy Pier. You can browse and book hundreds more Chicago tours, attractions and activities — many at up to 50% off — right on this page.

How much can I save on Chicago tours and attractions?

Smart Traveler travelers save up to 50% on Chicago attractions, tours and activities through exclusive industry rates and long-standing partnerships.

When is the best time to visit Chicago?

Late spring through early fall (May–October) offers warm weather, lakefront festivals and outdoor patios. Summer is the liveliest season, while fall brings crisp air and fewer crowds; winters are cold but sparkle with holiday markets.

Can a travel specialist plan my whole Chicago trip?

Yes. Beyond activities, our Chicago travel specialists arrange flights, hotels, cruises and complete packages. Request up to 5 free, no-obligation quotes and compare.