Top Picks for Chicago Experiences

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

Trip.com offers 23 Experiences in Chicago

Q: What are the best Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier The Chicago Theatre Tour Experience

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

BIG BUS Chicago hop-on hop-off bus tour Chicago Full Day Bike Rental Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier

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Discover 23 Experiences in Chicago on Trip.com, updated December 4, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From EUR 6.60 per person, with an average total of EUR 59.38. Choose the option that suits your plan.

With 10 verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Full Day Bike Rental", with 7 reviews and a 4.4 rating.

Now on Trip.com: "Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier", a 1-hour adventure in Chicago!

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

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

80% of Chicago Experiences now offer English-speaking guides

December is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Chicago Full Day Bike Rental.

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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23 Results for Chicago Experiences

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BIG BUS Chicago hop-on hop-off bus tour
󱩳Enjoy the beautiful scenery of Chicago on a convenient open-top double-decker bus.
English
5.0/5
Excellent· 3 reviews· 61 booked
From€31.04
Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier
󱩳Board the Chicago Architecture River Cruise and admire the stunning skyline
Duration: 1.5 hrs
English
From€50.14
The Chicago Theatre Tour Experience
Duration: 1 hr
English
From€25.84
Chicago River 45-min architecture cruise
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Duration: 45–60 mins
English
From€12.01
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
From€39.08
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
From€39.08
Architecture cruise on the Chicago River from Michigan Ave
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Duration: 75 mins
English
From€24.84
Chicago Odyssey Lake Michigan dinner cruise
󱩳Admire the skyline of Chicago
English
From€111.37
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
From€38.76
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
From€73.71
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
From€77.28
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
From€69.82
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
From€6.60
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
From€6.60
Chicago: Premier Dinner Cruise on the Chicago River
Duration: 150 mins
From€153.11
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
From€95.08
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
From€25.72
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
From€81.90
Book after inquiry/Route 66 Willis Tower Robie House Lincoln Park Airport in Chicago, USA/Point-to-point car service/Tour guide and driver/Private car service
󱩳Chinese-speaking driver at a fixed price (services available in Chinese and English)
English
From€80.48
Chicago Odyssey dinner cruise
󱩳Enjoy delicious and sophisticated lakefront dining
English
From€145.12