Top Picks for Chicago Experiences

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

Trip.com offers 42 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Chicago River 45-min architecture cruise Big Bus Chicago Hop-on Hop-off Bus Tour The Chicago Theatre Tour Experience

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

Skyline lake boat tour from Navy Pier Bite into Chicago: Discover the City’s Most Iconic Food Chicago River 45-min architecture cruise

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Discover 42 Experiences in Chicago on Trip.com, updated September 18, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From AED 51.43 per person, with an average total of AED 274.01. Choose the option that suits your plan.

With 80 verified reviews, Experiences Chicago boast an average rating of 4.8.

This week's most popular Experiences: "Bite into Chicago: Discover the City’s Most Iconic Food", with 79 reviews and a 4.7 rating.

Now on Trip.com: "Bite into Chicago: Discover the City’s Most Iconic Food", a 2-hour adventure in Chicago!

The next available day tour departs on September 19, 2025. Book now to secure your spot!

Chicago Experiences usually take about 2 hours — perfect for a relaxed, immersive experience!

75% of Chicago Experiences now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Experiences available day tours, including seasonal favorites like Bite into Chicago: Discover the City’s Most Iconic Food.

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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󱩳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 51.43

󱩳See the best of Chicago from the convenience and comfort of an open-top, double-decker bus. Hop on and hop off at any designated bus stop to explore major attractions at your own pace. Learn about the city's rich history from the informative commentary of a multilingual audio guide.