Top Picks for Chicago Experiences

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

Trip.com offers 44 Experiences in Chicago

Q: What are the best Experiences in Chicago?

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

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

Big Bus Chicago Hop-on Hop-off Bus Tour Skyline lake boat tour from Navy Pier Bite into Chicago: Discover the City’s Most Iconic Food

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Discover 44 Experiences in Chicago on Trip.com, updated November 4, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From SAR 52.51 per person, with an average total of SAR 311.28. Choose the option that suits your plan.

With 83 verified reviews, Experiences Chicago boast an average rating of 4.9.

This week's most popular Experiences: "Bite into Chicago: Discover the City’s Most Iconic Food", with 81 reviews and a 4.7 rating.

Now on Trip.com: "Bite into Chicago: Discover the City’s Most Iconic Food", a 2-hour adventure in Chicago!

The next available day tour departs on November 5, 2025. Book now to secure your spot!

Chicago Experiences usually take about 2 hours — perfect for a relaxed, immersive experience!

70% of Chicago Experiences now offer English-speaking guides

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.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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44 Results for Chicago Experiences

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Big Bus Chicago Hop-on Hop-off Bus Tour
󱩳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.
English
5.0/5
Excellent· 1 review· 34 booked
FromSAR 135.90
Chicago River 45-min architecture cruise
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Duration: 45–60 mins
English
FromSAR 52.51
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromSAR 111.85
Chicago Premier Lake Michigan brunch cruise
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Duration: 120 mins
English
FromSAR 388.79
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromSAR 159.47
Skyline lake boat tour from Navy Pier
󱩳Learn about Chicago's world-famous skyline cityscape and the history of Navy Pier
Duration: 45 mins
English
5.0/5
Excellent· 1 review
FromSAR 68.30
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 81 reviews
FromSAR 286.85
Chicago Odyssey dinner cruise
󱩳Enjoy delicious and sophisticated lakefront dining
English
FromSAR 747.53
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
󱩳Global language translation allows you to communicate without worries no matter where you are, and start your health journey with peace of mind.
FromSAR 58.40
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
FromSAR 657.22
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromSAR 167.75
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromSAR 369.05
Chicago: Canine Cruise
Duration: 90 mins
English
FromSAR 156.58
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromSAR 402.48
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromSAR 298.17
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
FromSAR 369.05
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromSAR 316.83
Chicago: Family & Food Guided Bike Tour
Duration: 4 hrs
English
FromSAR 298.17
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
FromSAR 406.86
Chicago: Premier Dinner Cruise on the Chicago River
Duration: 150 mins
FromSAR 773.89