Top Picks for Chicago Experiences

Q: How many Experiences are available in Chicago on Trip.com?

Trip.com offers 39 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago River 45-min architecture cruise Big Bus Chicago Hop-on Hop-off Bus Tour The Chicago Theatre Tour Experience

Q: What are the top-rated Experiences in Chicago?

Skyline lake boat tour from Navy Pier Bite into Chicago: Discover the City’s Most Iconic Food Chicago River 45-min architecture cruise

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Discover 39 Experiences in Chicago on Trip.com, updated November 22, 2025, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

With 76 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Bite into Chicago: Discover the City’s Most Iconic Food", with 75 reviews and a 4.7 rating.

The next available day tour departs on November 23, 2025. Book now to secure your spot!

Chicago Experiences usually take about 1 hours — perfect for a relaxed, immersive experience!

November is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Bite into Chicago: Discover the City’s Most Iconic Food.

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39 Results for Chicago Experiences

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󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromVND 371,726
󱩳See the best of Chicago from the convenience and comfort of an open-top, double-decker bus. Hop on and hop off at any designated bus stop to explore major attractions at your own pace. Learn about the city's rich history from the informative commentary of a multilingual audio guide.
Big Bus Chicago Hop-on Hop-off Bus Tour
English
FromVND 962,406
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromVND 796,466
Chicago Seadog: Extreme Thrill Ride
Duration: 30 mins
FromVND 1,360,434
Chicago Lakefront Fireworks Cruise
Duration: 1 hr
FromVND 1,645,219
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromVND 1,137,274
󱩳Global language translation allows you to communicate without worries no matter where you are, and start your health journey with peace of mind.
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
FromVND 20,128,825
󱩳Admire the skyline of Chicago
Spirit of Chicago dinner cruise
English
FromVND 3,100,460
󱩳Learn about Chicago's world-famous skyline cityscape and the history of Navy Pier
Skyline lake boat tour from Navy Pier
Duration: 45 mins
English
5.0/5
Excellent· 1 review
FromVND 483,510
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromVND 2,752,365
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 75 reviews
FromVND 2,030,686
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
FromVND 5,190,888
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromVND 769,208
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromVND 1,196,410
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromVND 2,259,608
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromVND 1,196,410
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromVND 2,631,852
Chicago: Canine Cruise
Duration: 90 mins
English
FromVND 1,115,176
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromVND 2,126,708
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
FromVND 2,631,852