App

Customer support

PHP

Find bookings

Top Picks for Chicago Experiences

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

Trip.com offers 45 Experiences in Chicago

Q: What are the best Experiences in Chicago?

Big Bus Chicago Hop-on Hop-off Bus Tour Chicago Architecture Sightseeing Cruise Experience [Departing 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 Bite into Chicago: Discover the City’s Most Iconic Food

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

Get help anytime, anywhere within 30 seconds Contact customer support



Discover 45 Experiences in Chicago on Trip.com, updated October 23, 2025, with experiences lasting from 1 to 24 hours. Find the perfect adventure for your day!

From PHP 907.04 per person, with an average total of PHP 4,584.05. Choose the option that suits your plan.

With 403 verified reviews, Experiences Chicago boast an average rating of 4.7.

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 Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier", a 1-hour adventure in Chicago!

The next available day tour departs on October 24, 2025. Book now to secure your spot!

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

60% of Chicago Experiences now offer English-speaking guides

October is perfect for visiting Chicago! Choose from Experiences available day tours, including seasonal hits 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

Available Today

Available Tomorrow

45 Results for Chicago Experiences

Sort by

Recommended

Big Bus Chicago Hop-on Hop-off Bus Tour
English
5.0/5
Excellent· 1 review· 40 booked
From
Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier
Duration: 1.5 hrs
English
From
All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States
From
Chicago Full Day Bike Rental
Duration: 24 hrs
English
4.3/5
Good· 6 reviews
From
Chicago: 90-Minute Architecture Tour on the Lake & River
Duration: 90 mins
From
Chicago Seadog: Lakefront Speedboat Tour
Duration: 30 mins
From
Lake Michigan & Chicago River: 75 Minute Speedboat Cruise
Duration: 75 mins
English
From
Chicago: Premier Dinner Cruise on Lake Michigan
Duration: 150 mins
From
Big Bus Chicago: Hop-on Hop-off Bus Tour
Duration: 2 hrs
English
From
Chicago: Food and Prohibition Architecture Guided Tour
Duration: 5 hrs
English
From
Chicago: Skyline Lake Tour
Duration: 45 mins
English
From
Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch
Duration: 2 hrs
From
Lake Michigan: Premier Brunch or Lunch Cruise
Duration: 2 hrs
From
Chicago Loop District Food Tour with Deep Dish & Beef Sandwich
Duration: 3 hrs
4.9/5
Excellent· 313 reviews
From
Chicago: Chinatown Food & Culture Walking Tour
Duration: 3 hrs
English
From
Chicago: Guided Food Tasting + Bike Tour
Duration: 4 hrs
English
From
Chicago: Guided Food Tour + Bike or Kayak Rental
Duration: 150 mins
English
From
Chicago: Family & Food Guided Bike Tour
Duration: 4 hrs
English
From
Chicago: Food Tour + Bike or Kayak Rental
Duration: 5 hrs
English
From
Bite into Chicago: Discover the City’s Most Iconic Food
Duration: 2 hrs
4.7/5
Great· 83 reviews
From





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?



Trip.com Picks

Popular Chicago Tours

Best Chicago Experiences

Recommended Events

Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters Millennium Park self-guided walking audio tour in Chicago Chicago Pizza Bus Tour Ticket Chicago Lake and River Architecture Tour Scenic Chicago Night Tour

Chicago Local Tour Guides Chicago City Pass Chicago Day Tours Chicago Connectivity Solutions Chicago Group Tours Chicago River 90-Minute Architecture Tour Chicago River 45-Minute Architecture Tour from Magnificent Mile Chicago Night Crimes Bus Tour: Criminals, Mobsters and Gangsters Scenic Chicago Night Tour Millennium Park self-guided walking audio tour in Chicago Guangzhou Spa & Massage Singapore Travel Essentials Japan SIM Card Shanghai Pocket Wifi Router Zhangjiajie Spa & Massage Mutianyu Great Wall Bus Tour with Activity Options Tiananmen Square, Forbidden City & Treasure Museum Small Group Tour Mutianyu Great Wall Round-trip by ZANBUS with Tickets, Daily Departure 8/9/10 AM Mutianyu Great Wall + Summer Palace 1-day tour Return ends at Bird's Nest Zhangjiajie National Forest Park One-Day Tour

Reviews/Trip Moments

★

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

Guest User2025-09-21

The app was very convenient as it told me where the bus was. It said the bus was every 30 minutes, but it seemed to come a little earlier.

★

Reviews: Chicago Full Day Bike Rental

Guest User2024-09-02

Very well organized! Well located for access to Lakefront Trail! We took the Confort Hybrid bikes and 4 very happy adults! I recommend without hesitation:-)