Top Picks for Chicago Experiences

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

Trip.com offers 45 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Big Bus Chicago Hop-on Hop-off Bus Tour Chicago: 90-Minute Architecture Tour on the Lake & River Chicago River 45-min architecture cruise

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 Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

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Discover 45 Experiences in Chicago on Trip.com, updated November 3, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From USD 14.00 per person, with an average total of USD 74.51. Choose the option that suits your plan.

With 403 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Chicago Loop District Food Tour with Deep Dish & Beef Sandwich", with 313 reviews and a 4.9 rating.

Now on Trip.com: "Big Bus Chicago: Hop-on Hop-off Bus Tour", a 2-hour adventure in Chicago!

The next available day tour departs on November 4, 2025. Book now to secure your spot!

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

65% of Chicago Experiences now offer English-speaking guides

November is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits like Chicago Loop District Food Tour with Deep Dish & Beef Sandwich.

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

Search attractions or local attractions & tours

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45 Results for Chicago Experiences

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󱩳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
5.0/5
Excellent· 1 review· 39 booked
FromUS$36.32
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromUS$45.02
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromUS$14.00
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
FromUS$42.80
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromUS$45.07
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromUS$99.15
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromUS$80.12
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
FromUS$99.15
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromUS$85.03
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 82 reviews
FromUS$76.48
󱩳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
FromUS$18.21
Chicago: Skyline Lake Tour
Duration: 45 mins
English
FromUS$37.59
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromUS$30.02
󱩳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
FromUS$15.61
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
FromUS$199.31
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromUS$89.00
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.3/5
Good· 6 reviews
FromUS$29.99
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromUS$135.36
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
FromUS$203.96
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
FromUS$108.03