App

Customer support

AUD

Find bookings

Top Picks for Chicago Experiences

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

Trip.com offers 44 Experiences in Chicago

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

Skyline lake boat tour from Navy Pier Big Bus Chicago Hop-on Hop-off Bus Tour Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

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

Get help anytime, anywhere within 30 seconds Contact customer support



Discover 44 Experiences in Chicago on Trip.com, updated September 28, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From AUD 21.38 per person, with an average total of AUD 118.15. Choose the option that suits your plan.

With 396 verified reviews, Experiences Chicago boast an average rating of 4.9.

This week's most popular Experiences: "Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More", with 313 reviews and a 4.9 rating.

Now on Trip.com: "Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier", a 1-hour adventure in Chicago!

The next available day tour departs on September 29, 2025. Book now to secure your spot!

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

70% of Chicago Experiences now offer English-speaking guides

September is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits like Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More.

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

Transport

Travel essentials

Experiences

Day tours

Date

Top Picks

Available Today

Available Tomorrow

44 Results for Chicago Experiences

Sort by

Recommended

Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier

󱩳Climb aboard a Chicago Architecture River Cruise and admire the stunning skyline

Duration: 1.5 hrs

English

FromAU$74.42

The Chicago Theatre Tour Experience

Duration: 1 hr

English

FromAU$45.80

Chicago: Food Tour + Bike or Kayak Rental

Duration: 5 hrs

English

FromAU$166.64

Skyline lake boat tour from Navy Pier

󱩳Learn about Chicago's world-famous skyline cityscape and the history of Navy Pier

Duration: 45 mins

English

5.0/5

Excellent· 1 review

FromAU$27.80

Chicago favorites food walking tour

󱩳Taste your way through the Windy City's finger-licking food scene

Duration: 180 mins

FromAU$122.11

Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

Duration: 3 hrs

4.9/5

Excellent· 313 reviews

FromAU$135.86

Chicago: 90-Minute Architecture Tour on the Lake & River

Duration: 90 mins

FromAU$68.71

Architecture cruise on the Chicago River from Michigan Ave

󱩳Admire Chicago's amazing urban architecture from the Chicago River

Duration: 75 mins

English

FromAU$44.23

Chicago River 45-min architecture cruise

󱩳Navigate all three branches of the Chicago River in a fully equipped vessel

Duration: 45–60 mins

English

FromAU$21.38

Chicago: Chinatown Food & Culture Walking Tour

Duration: 3 hrs

English

FromAU$122.13

Chicago Odyssey dinner cruise

󱩳Enjoy delicious and sophisticated lakefront dining

English

FromAU$304.25

Big Bus Chicago Hop-on Hop-off Bus Tour

󱩳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.

English

5.0/5

Excellent· 1 review· 34 booked

FromAU$55.28

Chicago Premier Lake Michigan brunch cruise

󱩳Enjoy a buffet-style brunch with freshly prepared entrees, salads and desserts

Duration: 120 mins

English

FromAU$158.24

Chicago Seadog: Lakefront Speedboat Tour

Duration: 30 mins

FromAU$65.32

Bite into Chicago: Discover the City’s Most Iconic Food

Duration: 2 hrs

4.7/5

Great· 81 reviews

FromAU$116.75

Chicago: Premier Dinner Cruise on Lake Michigan

Duration: 150 mins

FromAU$269.17

Big Bus Chicago: Hop-on Hop-off Bus Tour

Duration: 2 hrs

English

FromAU$68.71

Chicago: Food and Prohibition Architecture Guided Tour

Duration: 5 hrs

English

FromAU$151.15

Chicago: Canine Cruise

Duration: 90 mins

English

FromAU$64.12

Lake Michigan & Chicago River: 75 Minute Speedboat Cruise

Duration: 75 mins

English

FromAU$206.59

Lake Michigan: Premier Brunch or Lunch Cruise

Duration: 2 hrs

FromAU$144.00

Chicago: Guided Food Tasting + Bike Tour

Duration: 4 hrs

English

FromAU$151.15

Chicago: Guided Food Tour + Bike or Kayak Rental

Duration: 150 mins

English

FromAU$129.76

Chicago: Family & Food Guided Bike Tour

Duration: 4 hrs

English

FromAU$122.13





Frequently asked questions about Chicago Experiences

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



What are the best Experiences in Chicago?



What are the top-rated Experiences in Chicago?



How can I contact Trip.com customer support?



Reviews/Trip Moments

★

Reviews: Skyline lake boat tour from Navy Pier

Guest User2025-06-25

When booking on line and getting tickets emailed, information about which doc the boat is on would be great. We live out of state and had no idea which boat it was, where the doc is located we missed our time for departure. Luckily my tickets were honored for a later time.

★

Reviews: Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

Guest User2024-07-19

Sue was an excellent guide and host…highly recommend. In addition to the food knowledge, Sue showed us some great architectural and unique information about the great city of Chicago.

Contact us

About

Other services

Payment methods

Our partners

Contact Center
of the year 2024

Trip.com is part of Trip.com Group Limited, one of the world's leading providers of travel services.