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The Best Things to Do in Chicago | Updated March 2026

Chicago

Discover Chicago’s legendary skyline on a 75-minute architecture river cruise with live narration and views of 40+ iconic landmarks.

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Discover a world of mind-bending fun at the Museum of Illusions Chicago with 80+ interactive rooms and all-new visual experiences.

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Explore Chicago's iconic sites aboard the Big Bus enjoying stunning views and comfortable seating as you hop on and off at top attractions throughout the city. Create your adventure!

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Explore Frank Lloyd Wright’s Prairie Style masterpiece at the UNESCO-listed Frederick C. Robie House in Chicago.

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Explore dinosaurs, gems, and 40 million artifacts with entry to Chicago’s iconic Field Museum of Natural History.

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Skip the lines at The Art Institute of Chicago and explore world-famous masterpieces by Picasso, Monet, van Gogh, Dalí, Warhol, and more.

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Soar above the Magnificent Mile at 360 Chicago and enjoy stunning 360° skyline and lake views from the 94th floor of the John Hancock Center.

Soaring high above Chicago's skyline the 360 CHICAGO Observation Deck reveals stunning views of Lake Michigan and the city allowing for unforgettable photo opportunities and a serene escape from the bustling streets below.

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The Best Things to Do in
Chicago

Chicago: Architecture River Cruise from Navy Pier

Chicago C3® CityPASS®: 3 Attractions of your choice

Museum of Illusions Chicago Tickets

Chicago Bike & Classic Food Tour: Bikes, Bites & Views - Adults

Chicago City Minibus Tour

Big Bus Chicago: Hop-On Hop-Off Sightseeing Tour, 24/48/72hr Pass

Frank Lloyd Wright Robie House Tickets

Chicago Foods Tour with The Loop, Skyline, Millennium Park

Private Transfer from Newport Cruise Port to Boston city hotels

Chicago Walking Tour: A Walk Through Time

LEGOLAND® Discovery Center Chicago Tickets

Lakefront Segway Tour in Chicago

Lake Michigan: Premier Brunch or Lunch Cruise

The Field Museum of Natural History Tickets

Medieval Torture Museum: Entry Ticket

Flyover Experience in Chicago

Walkin' with Colin: Chicago History-Mystery-Comedy-Tragedy Tour

The Art Institute of Chicago: Fast Pass

American Writers Museum: Entry Ticket

360 Chicago Observation Deck Tickets