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Top Picks for Chicago Experiences

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

Trip.com offers 38 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 Chicago in a Day: Food, History & Architecture Walking Tour

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

BIG BUS Chicago hop-on hop-off bus tour Chicago in a Day: Food, History & Architecture Walking Tour Chicago Full Day Bike Rental

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Discover 38 Experiences in Chicago on Trip.com, updated November 26, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From RUB 602.53 per person, with an average total of RUB 4,967.08. Choose the option that suits your plan.

With 34 verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago in a Day: Food, History & Architecture Walking Tour", with 24 reviews and a 4.8 rating.

Now on Trip.com: "Chicago in a Day: Food, History & Architecture Walking Tour", a 4-hour adventure in Chicago!

The next available day tour departs on November 27, 2025. Book now to secure your spot!

Chicago Experiences usually take about 4 hours — perfect for a relaxed, immersive experience!

75% 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 in a Day: Food, History & Architecture Walking Tour.

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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38 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
FromRUB 2,842.29
Chicago River 45-min architecture cruise
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Duration: 45–60 mins
English
FromRUB 1,099.67
Chicago in a Day: Food, History & Architecture Walking Tour
󱩳Explore Chicago's iconic architecture on foot,
Duration: 4.5 hrs
4.8/5
Great· 24 reviews
5% off
Limited-time sale
FromRUB 7,419.88RUB 7,810.4
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
FromRUB 4,579.20
Architecture cruise on the Chicago River from Michigan Ave
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Duration: 75 mins
English
FromRUB 2,275.53
Chicago Odyssey Lake Michigan dinner cruise
󱩳Admire the skyline of Chicago
English
FromRUB 10,203.35
The Chicago Theatre Tour Experience
Duration: 1 hr
English
FromRUB 2,366.30
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
FromRUB 6,698.14
Festive Chicago food and walking tour
󱩳Wander through Millennium Park, State Street and The Loop
English
FromRUB 784.70
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromRUB 602.53
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
󱩳Exquisite flavors with consistently high quality
English
FromRUB 602.53
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromRUB 3,551.26
Architecture cruise on the Chicago River from Navy Pier
󱩳Enjoy panoramic skyline views from along the Chicago River
Duration: 75 mins
English
FromRUB 2,296.74
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromRUB 3,551.26
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromRUB 8,640.06
Chicago Odyssey dinner cruise
󱩳Enjoy delicious and sophisticated lakefront dining
English
FromRUB 15,356.07
Chicago: Premier Dinner Cruise on the Chicago River
Duration: 150 mins
FromRUB 16,071.52
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
󱩳Exquisite flavors with consistently high quality
English
FromRUB 602.53
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromRUB 2,355.65
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromRUB 7,442.37

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Frequently asked questions about Chicago Experiences

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Reviews/Trip Moments

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Reviews: BIG BUS Chicago hop-on hop-off bus tour

Guest User2025-11-06

It’s a nice experience for those who have a short visit to Chicago. One can see the main attractions and city highlights in 24 hrs ticket. 48 hrs ticket only recommended if wishing to use the cruise, otherwise 24 hrs are enough to see the city

★

Reviews: Chicago in a Day: Food, History & Architecture Walking Tour

Guest User2025-10-22

Dave was an excellent guide! He was informative, professional and a lot of fun. He shared many interesting facts and was very entertaining. We certainly saw and covered a lot of ground but it didn't feel that way. Our food stops were perfect - don't eat before you go! This is such a great way to get to know the city and I would recommend doing it at the beginning of your trip for all of the amazing tips to use during your stay.