Top Picks for Chicago Experiences

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

Trip.com offers 24 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 Chicago River 45-min architecture cruise

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

From PHP 449.53 per person, with an average total of PHP 3,792.12. 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 4, 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 perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits 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.

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24 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
FromPHP 2,121.58
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
FromPHP 3,416.41
Chicago River 45-min architecture cruise
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Duration: 45–60 mins
English
FromPHP 818.99
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromPHP 1,757.81
Architecture cruise on the Chicago River from Michigan Ave
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Duration: 75 mins
English
FromPHP 1,694.71
Chicago Odyssey Lake Michigan dinner cruise
󱩳Admire the skyline of Chicago
English
FromPHP 7,598.99
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromPHP 2,658.48
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromPHP 449.53
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromPHP 449.53
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
FromPHP 2,636.71
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromPHP 2,658.48
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
FromPHP 5,014.24
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromPHP 5,257.09
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
FromPHP 4,749.61
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromPHP 6,467.96
Chicago: Premier Dinner Cruise on the Chicago River
Duration: 150 mins
FromPHP 10,415.54
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
󱩳Exquisite flavors with consistently high quality
English
FromPHP 449.53
Chicago Odyssey dinner cruise
󱩳Enjoy delicious and sophisticated lakefront dining
English
FromPHP 9,901.50
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromPHP 1,754.38
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromPHP 5,571.37