Top Picks for Chicago Experiences

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

Trip.com offers 26 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 Chicago: Taste of Chinatown Food Walking Tour

Q: How can I contact Trip.com customer support?

Get help anytime, anywhere within 30 seconds Contact customer support

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.



Discover 26 Experiences in Chicago on Trip.com, updated November 26, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From GBP 7.59 per person, with an average total of GBP 53.82. Choose the option that suits your plan.

With 430 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 27, 2025. Book now to secure your spot!

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

75% 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



Trip.comChicago

Experiences

Experiences

Top Picks

Available Today

Available Tomorrow

26 Results for Chicago Experiences

Sort by

Recommended

󱩳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£27.48
󱩳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£44.20
󱩳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£11.89
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.4/5
Good· 7 reviews
From£22.79
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
From£67.62
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 86 reviews
From£58.11
󱩳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£22.01
󱩳Take an exciting speedboat ride
Chicago's River and Lake architecture speedboat cruise
Duration: 75 mins
English
From£41.16
󱩳Taste your way through the Windy City's finger-licking food scene
Chicago favorites food walking tour
Duration: 180 mins
From£60.78
󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts
Chicago Premier Lake Michigan brunch cruise
Duration: 120 mins
English
From£88.72
󱩳Enjoy delicious and sophisticated lakefront dining
Chicago Odyssey dinner cruise
English
From£148.54
󱩳Tease your taste buds and join this tour in the River North and Wicker Park neighborhoods
River North food tour
English
From£60.02
󱩳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
From£56.99
󱩳Admire Chicago's amazing urban architecture from the Chicago River
Architecture cruise on the Chicago River from Michigan Ave
Duration: 75 mins
English
From£22.01
󱩳Wander through Millennium Park, State Street and The Loop
Festive Chicago food and walking tour
English
From£7.59
󱩳Admire the skyline of Chicago
Chicago Odyssey Lake Michigan dinner cruise
English
From£98.70
󱩳Immerse yourself in the world of motorcycles at the Harley-Davidson Museum
Chicago:Milwaukee City Highlights Day Trip with Brewery Tour
Duration: 8 hrs
English
From£94.97
󱩳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
From£70.95
󱩳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
From£61.33£64.56