Best Experiences in Central Chicago

Local Recommendations from our My Guide Chicago team

Discover the best experiences in Chicago curated by local experts. Explore the hidden gems and must-see attractions of the Windy City.

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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Best Seller

Chicago: 45-Minute Family-Friendly Architecture River Cruise

1177 Reviews

Chicago: 45-Minute Family-Friendly Architecture River Cruise

Cruise down the Chicago River and see the city’s most spectacular landmarks on a boat cruise with live, family-friendly commentary and a full-service bar on board.

$28.00

From

Best Seller

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

842 Reviews

Chicago: Hop-on Hop-off Sightseeing Tour by Open-top Bus

Explore Chicago at your own pace with a Big Bus hop-on hop-off tour or sunset tour. See Chicago's landmarks including Willis Tower, Navy Pier, and Magnificent Mile from an open-top double-decker bus.

$49.50

From

Best Seller

Chicago: All-Inclusive Pass with 30+ Attractions

346 Reviews

Chicago: All-Inclusive Pass with 30+ Attractions

Save up to 50% on admission to over 30 attractions in Chicago. Visit sites like 360 Chicago, Skydeck Chicago and the Ledge, Architectural River Cruise, Shedd Aquarium, Museum of Science, and more.

$129.00

From

Best Seller

Chicago: Bikes, Bites, and Brews Biking Tour

112 Reviews

Chicago: Bikes, Bites, and Brews Biking Tour

Sample Chicago’s four favorite food groups – pizza, hot dogs, brownies, and beer – on this city bike tour. Tour Chicago's famous neighborhoods and top attractions, day and night tour routes.

$89.99

From

Best Seller

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

1512 Reviews

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Soar to heights of nearly 200 feet over Navy Pier, with unparalleled, 360-degree views of Chicago and Lake Michigan. Choose between pre-purchasing a Regular or a Fastpass Express ticket to experience this iconic part of the Chicago skyline.

$21.30

From

Best Seller

Chicago: Museum of Ice Cream Entry Ticket

115 Reviews

Chicago: Museum of Ice Cream Entry Ticket

Enjoy a fully immersive experience at the Museum of Ice Cream, delivering joy and entertainment for the whole family. Savor signature ice cream flavors and sweet treats as you explore the museum.

$31.97

From

Best Seller

Chicago River: 1.5-Hour Guided Architecture Cruise

4624 Reviews

Chicago River: 1.5-Hour Guided Architecture Cruise

Experience Chicago’s legendary architecture from the best seat in the house: the river. Enjoy a comprehensive tour with a live fun guide as you navigate through the heart of the city covering all 3 branches of the Chicago River.

$44.00

From

Best Seller

Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise

42 Reviews

Chicago: Small-Group Night Tour w/ Skydeck & Skyline Cruise

Experience Chicago's most prominent sights on this night tour with hotel transfers. Enjoy a skyline cruise of the Windy City, and head to the top of the Skydeck observation deck at Willis Tower.

$204.00

From

Best Seller

Chicago: 360 Chicago Observation Deck General Admission

1894 Reviews

Chicago: 360 Chicago Observation Deck General Admission

Skip the ticket purchase desk to enjoy the best panoramic views of Chicago, 94 stories above the Windy City. Enjoy stunning lake views and close-up vistas of Chicago’s amazing skyscrapers.

$30.00

From

Best Seller

Chicago: Mob and Crime Bus Tour

626 Reviews

Chicago: Mob and Crime Bus Tour

Experience the dark side of the Windy City on a Crime and Mob Bus Tour that introduces you to Chicago’s history of crime. Escape into the city's underworld and learn about characters like Al Capone and John Dillinger.

$46.00

From

Best Seller

Chicago: Gangsters and Ghosts Guided Walking Tour

1041 Reviews

Chicago: Gangsters and Ghosts Guided Walking Tour

Embark on a history-based guided walking tour and discover the stories of Chicago’s gangsters and ghosts. Learn about the city’s darker side and creepy past as you explore the Chicago Loop district.

$35.00

From

Best Seller

Chicago: Explorer Pass with Choice of 2-7 Attractions

340 Reviews

Chicago: Explorer Pass with Choice of 2-7 Attractions

Save up to 50%* on admission to 2, 3, 4, 5, 6, or 7 Chicago attraction including 360 Chicago, Architecture River Cruise, Skydeck Chicago, and much more.

$84.00

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