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Top picks for Chicago Experiences

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

Trip.com offers 9 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago Downtown + Millennium Park Day Tour in the US Chicago: Magnificent Mile Tour With Optional 360 Chicago Chicago Highlights Walking Tour with Skydeck & Cruise

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

Chicago: Magnificent Mile Tour With Optional 360 Chicago Chicago Highlights Walking Tour with Skydeck & Cruise BIG BUS Chicago hop-on hop-off bus tour

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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 9 Experiences in Chicago on Trip.com, updated April 28, 2026, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From MXN 138.33 per person, with an average total of MXN 1,385.73. Choose the option that suits your plan.

With 3.324k verified reviews, Experiences Chicago boast an average rating of 4.7.

This week's most popular Experiences: "Chicago Favorites Ultimate Food and Walking Tour", with 1.96k reviews and a 4.8 rating.

Now on Trip.com: "Chicago Downtown + Millennium Park Day Tour in the US", a 5-hour adventure in Chicago!

The next available day tour departs on April 29, 2026. Book now to secure your spot!

Chicago Experiences usually take about 5 hours — perfect for a relaxed, immersive experience!

67% of Chicago Experiences now offer English-speaking guides

April is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Chicago Favorites Ultimate Food and 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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9 results for Chicago Experiences

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Recommended

Chicago Downtown + Millennium Park Day Tour in the US
Duration: 5.7 hrs
English
4.5/5
Excellent· 4 reviews
FromMXN$2,606.58
Chicago: Magnificent Mile Tour With Optional 360 Chicago
Duration: 2–3 hrs
English
5.0/5
Perfect· 2 reviews
5% off

Limited-time sale
FromMXN$693.88MXN$730.4
Chicago Highlights Walking Tour with Skydeck & Cruise
Duration: 4 hrs
English
5.0/5
Perfect· 3 reviews
5% off

Limited-time sale
FromMXN$3,106.67MXN$3,270.18
Alinea, the popular restaurant in Chicago, USA - Restaurant Reservation Service
English
FromMXN$138.33
Restaurant Reservation Service for the Trendy Addison Restaurant in Chicago, USA
English
FromMXN$138.33
Reservation service for the popular Eleven Madison Park restaurant in Chicago, USA
English
FromMXN$138.33
Small Group Max 12: Chicago Architecture and Aesthetics Tour
Duration: 1.8 hrs
English
FromMXN$834.11
From Chicago: 1-Day Tour on Galena
Duration: 1 day
English
5% off

Limited-time sale
FromMXN$2,180.6MXN$2,295.37
Chicago: Mimosa n' Bloody Mary Cruise
Duration: 1.5 hrs
English
4.0/5
Very good· 1 review
5% off

Limited-time sale
FromMXN$627.65MXN$660.69
Chicago: Moonlight Paddle Tour on the Chicago River
Duration: 1.5 hrs
English
4.2/5
Very good· 5 reviews
5% off

Limited-time sale
FromMXN$937.88MXN$987.25
Chicago: Sunset Kayak Tour on the Chicago River
Duration: 1.5 hrs
English
4.0/5
Very good· 3 reviews
5% off

Limited-time sale
FromMXN$949.89MXN$999.89
Chicago round-trip|Dubuque Town + Galena Town + Grant Park
Duration: 9 hrs
English
FromMXN$1,795.65
Chicago: Architecture River Cruise Skip-the-Ticket Line
Duration: 1–1.5 hrs
4.9/5
Perfect· 89 reviews· 32 booked
FromMXN$678.22
BIG BUS Chicago hop-on hop-off bus tour
English
5.0/5
Perfect· 6 reviews· 73 booked
FromMXN$701.11
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
FromMXN$1,721.73
Chicago to Milwaukee Landmarks Day Trip w/optional Miller Brewery & Harley Davidson Museum
Duration: 8 hrs
English
FromMXN$3,284.29
Chicago: Craft Brewery Barrel Bus Tour
Duration: 225 mins
English
FromMXN$1,731.92
iFLY Chicago Lincoln Park: First Time Flyer Experience
Duration: 1.5 hrs
English
5.0/5
Perfect· 3 reviews
5% off

Limited-time sale
FromMXN$2,250.7MXN$2,369.16
Studio W.I.P. - Uptown Chicago: Spray Paint & Sip Urban Art Workshop
Duration: 90 mins
English
FromMXN$782.59
Chicago: Signature Dishes Bike Tour
Duration: 4 hrs
English
FromMXN$1,564.76
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Very good· 7 reviews
FromMXN$521.15
Chicago Favorites Ultimate Food and Walking Tour
Duration: 3 hrs
4.8/5
Outstanding· 2k reviews
FromMXN$1,476.89
Delicious Donuts & City Sights: Chicago's Original Donut Tour
Duration: 2 hrs
4.9/5
Perfect· 895 reviews
FromMXN$1,216.41
Chicago: Classic Food & Walking Tour with Free Bike or Kayak
Duration: 3 hrs
4.9/5
Perfect· 8 reviews
5% off

Limited-time sale
FromMXN$1,404.02MXN$1,477.92
Chicago: Taste of Chinatown Food and Cultural Walking Tour
Duration: 3 hrs
5.0/5
Perfect· 24 reviews
5% off

Limited-time sale
FromMXN$1,404.02MXN$1,477.92
Chicago: Tapas & Flamenco Dinner in Ukrainian Village
Duration: 2 hrs
5.0/5
Perfect· 1 review
5% off

Limited-time sale
FromMXN$2,802.43MXN$2,949.93
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Perfect· 313 reviews
FromMXN$1,476.89
Chicago: Westside Food Tasting Bike Tour with Guide
Duration: 4 hrs
5% off

Limited-time sale
FromMXN$1,635.45MXN$1,721.53

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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?

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What are the top-rated Experiences in Chicago?



What are the recommended itineraries in Chicago?

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How can I contact Trip.com customer support?

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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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Reviews/Trip Moments

★

Reviews: Chicago Downtown + Millennium Park Day Tour in the US

Guest User2024-07-02

The driver was super nice, punctual, and friendly. A great experience overall, excellent service, and great value for money.

★

Reviews: Chicago: Magnificent Mile Tour With Optional 360 Chicago

Guest User2025-06-18

Our Mag Mile Tour was great. We learned about the architecture of buildings, design details and history of the area. Our guide Ben was knowledgeable, friendly, full of facts and anecdotes. It was a perfect distance - enough to see the major sites without being too long. We followed with the 360 Chicago at the Hancock. Great tour would highly recommend.

★

Reviews: Chicago Highlights Walking Tour with Skydeck & Cruise

Guest User2025-04-14

The tour was excellent Andrew did a wonderful job. He was very knowledgeable about Chicago history the buildings. Both experiences the sky deck, and the boat were great too. Highly recommend the tour just make sure to wear warm coat and comfortable shoes.