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Top Picks for Chicago Experiences

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

Trip.com offers 41 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 All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

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

BIG BUS Chicago hop-on hop-off bus tour Chicago Loop District Food Tour with Deep Dish & Beef Sandwich Bite into Chicago: Discover the City’s Most Iconic Food

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Q: Can I change or cancel my booking?

Change and cancellation policies vary by attractions and tours. Please check the product details page for more information.

Q: How can I get discounted prices?

Ticket prices may vary between weekdays and weekends, as well as during peak and off-peak seasons. When booking with Trip.com, you can also use Trip Coins to get extra savings. For more tips on booking discounted tickets, please visit Trip.com for the latest information.

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Discover 41 Experiences in Chicago on Trip.com, updated November 15, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From GBP 10.64 per person, with an average total of GBP 48.71. Choose the option that suits your plan.

With 409 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: "Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier", a 1-hour adventure in Chicago!

The next available day tour departs on November 16, 2025. Book now to secure your spot!

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

65% 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 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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41 Results for Chicago Experiences

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󱩳Enjoy the beautiful scenery of Chicago on a convenient open-top double-decker bus.
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Excellent· 3 reviews· 60 booked
From£27.50
󱩳Board the Chicago Architecture River Cruise and admire the stunning skyline
Chicago Architecture Cruise Experience from Michigan Avenue|Depart from Navy Pier
Duration: 1.5 hrs
English
From£44.04
󱩳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
From£11.85
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
From£22.78
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
From£34.18
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
From£83.20
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
From£102.75
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
From£34.18
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
From£67.71
Chicago: Skyline Lake Tour
Duration: 45 mins
English
From£25.69
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
From£73.80
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
From£71.62
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
From£67.59
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
From£54.67
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
From£64.54
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
From£74.60
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 86 reviews
From£58.08
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
From£10.64
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
From£22.00
The Chicago Theatre Tour Experience
Duration: 1 hr
English
From£22.78

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Frequently asked questions about Chicago Experiences

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

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What are the best Experiences in Chicago?



What are the top-rated Experiences in Chicago?

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Can I change or cancel my booking?

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How can I get discounted prices?

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Trip.com Picks

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Best 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 Full Day Bike Rental

Guest User2025-10-18

Easy process, great communication, rode the 7 speed city comfort bikes to Evanston and back. A very enjoyable ride. Appreciated the locks included in the rental.