Top Picks for Chicago Experiences

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

Trip.com offers 25 Experiences in Chicago

Q: What are the best Experiences in Chicago?

BIG BUS Chicago hop-on hop-off bus tour Chicago in a Day: Food, History & Architecture Walking Tour Chicago River 45-min architecture cruise

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

BIG BUS Chicago hop-on hop-off bus tour Chicago: Classic Food and Walking Tour with Free Bike/Kayak Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

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Discover 25 Experiences in Chicago on Trip.com, updated November 22, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From NZD 17.81 per person, with an average total of NZD 130.73. Choose the option that suits your plan.

With 465 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 in a Day: Food, History & Architecture Walking Tour", a 4-hour adventure in Chicago!

The next available day tour departs on November 23, 2025. Book now to secure your spot!

Chicago Experiences usually take about 4 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.

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25 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· 61 booked
FromNZD 64.55
󱩳Explore Chicago's iconic architecture on foot,
Chicago in a Day: Food, History & Architecture Walking Tour
Duration: 4.5 hrs
4.8/5
Great· 24 reviews
5% off
Limited-time sale
FromNZD 166.97NZD 175.76
󱩳Navigate all three branches of the Chicago River in a fully equipped vessel
Chicago River 45-min architecture cruise
Duration: 45–60 mins
English
FromNZD 24.95
󱩳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
FromNZD 103.48
󱩳Wander through Millennium Park, State Street and The Loop
Festive Chicago food and walking tour
English
FromNZD 17.81
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
FromNZD 51.63
󱩳Admire the skyline of Chicago
Chicago Odyssey Lake Michigan dinner cruise
English
FromNZD 231.48
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
FromNZD 348.38
󱩳Enjoy panoramic skyline views from along the Chicago River
Architecture cruise on the Chicago River from Navy Pier
Duration: 75 mins
English
FromNZD 51.63
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
FromNZD 53.45
󱩳Chinese-speaking driver at a fixed price (services available in Chinese and English)
Book after inquiry/Route 66 Willis Tower Robie House Lincoln Park Airport in Chicago, USA/Point-to-point car service/Tour guide and driver/Private car service
English
FromNZD 166.10
󱩳Get a taste of Chicago's most famous food in one of the city's most historic neighborhoods
Chicago ultimate food experience
Duration: 120 mins
English
FromNZD 133.65
󱩳Tease your taste buds and join this tour in the River North and Wicker Park neighborhoods
River North food tour
English
FromNZD 140.78
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
FromNZD 208.09
󱩳Enjoy a classic Chicago Italian Beef sandwich and original recipe brownie
Chicago: Classic Food and Walking Tour with Free Bike/Kayak
Duration: 3 hrs
5.0/5
Excellent· 5 reviews
5% off
Limited-time sale
FromNZD 134.90NZD 142.01
󱩳Enjoy a VIP Christmas adult beverage sampling package (for an additional fee)
Chicago: Guided Holiday Walking Tour and Food Sampling
Duration: 3 hrs
4.6/5
Satisfactory· 5 reviews
5% off
Limited-time sale
FromNZD 135.41NZD 142.54
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 87 reviews
FromNZD 136.29
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
FromNZD 158.60
󱩳Learn about the vibrant history of Chicago's Chinatown
Chicago: Taste of Chinatown Food Walking Tour
Duration: 2.5 hrs
4.8/5
Great· 21 reviews
5% off
Limited-time sale
FromNZD 143.99NZD 151.57
󱩳Taste your way through the Windy City's finger-licking food scene
Chicago favorites food walking tour
Duration: 180 mins
FromNZD 142.55