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.

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Discover 41 Experiences in Chicago on Trip.com, updated November 9, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From AED 51.42 per person, with an average total of AED 246.96. Choose the option that suits your plan.

With 408 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 10, 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· 2 reviews· 53 booked
FromAED 132.88
󱩳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
FromAED 212.76
󱩳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
FromAED 57.24
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromAED 110.15
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
FromAED 165.30
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
FromAED 447.34
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
FromAED 497.02
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
FromAED 165.30
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
FromAED 327.30
Chicago: Skyline Lake Tour
Duration: 45 mins
English
FromAED 124.19
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
FromAED 356.97
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
FromAED 346.42
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromAED 326.87
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
FromAED 264.45
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
FromAED 312.19
Chicago: Family & Food Guided Bike Tour
Duration: 4 hrs
English
FromAED 293.83
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
FromAED 360.31
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 86 reviews
FromAED 280.89
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromAED 51.42
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromAED 106.40