App
Customer support
EUR
Find bookings
ChicagoExperiences
ChicagoExperiences

Top Picks for Chicago Experiences

Discover 44 Experiences in Chicago on Trip.com, updated September 24, 2025, with experiences lasting from 1 to 5 hours. Find the perfect adventure for your day!

From EUR 8.47 per person, with an average total of EUR 59.84. 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 25, 2025. Book now to secure your spot!

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

66% 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 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.comChicago
Experiences
Top Picks
Available Today
Available Tomorrow

44 Results for Chicago Experiences

  • The Chicago Theatre Tour Experience

    The Chicago Theatre Tour Experience

    Duration: 1 hr
    English
    From€ 25,41
  • Chicago Architecture Sightseeing Cruise Experience [Departing from Michigan Avenue]|Depart from Navy Pier

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

    Duration: 1.5 hrs
    English
    From€ 41,43
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    From€ 92,45
  • Festive Chicago food and walking tour

    Festive Chicago food and walking tour

    English
    From€ 8,47
  • Chicago favorites food walking tour

    Chicago favorites food walking tour

    Duration: 180 mins
    From€ 67,78
  • Downtown Classics Food Tour: Deep Dish, Beef Sandwich & More

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

    Duration: 3 hrs
    4.9/5
    Excellent· 313 reviews
    From€ 75,41
  • Chicago: 90-Minute Architecture Tour on the Lake & River

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

    Duration: 90 mins
    From€ 38,12
  • Architecture cruise on the Chicago River from Michigan Ave

    Architecture cruise on the Chicago River from Michigan Ave

    Duration: 75 mins
    English
    From€ 24,55
  • Chicago River 45-min architecture cruise

    Chicago River 45-min architecture cruise

    Duration: 45–60 mins
    English
    From€ 11,87
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    From€ 67,76
  • Chicago Odyssey dinner cruise

    Chicago Odyssey dinner cruise

    English
    From€ 168,88
  • Big Bus Chicago Hop-on Hop-off Bus Tour

    Big Bus Chicago Hop-on Hop-off Bus Tour

    English
    5.0/5
    Excellent· 1 review· 34 booked
    From€ 30,68
  • Chicago Premier Lake Michigan brunch cruise

    Chicago Premier Lake Michigan brunch cruise

    Duration: 120 mins
    English
    From€ 87,84
  • Chicago Seadog: Lakefront Speedboat Tour

    Chicago Seadog: Lakefront Speedboat Tour

    Duration: 30 mins
    From€ 36,24
  • Skyline lake boat tour from Navy Pier

    Skyline lake boat tour from Navy Pier

    Duration: 45 mins
    English
    5.0/5
    Excellent· 1 review
    From€ 15,43
  • Bite into Chicago: Discover the City’s Most Iconic Food

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

    Duration: 2 hrs
    4.7/5
    Great· 81 reviews
    From€ 64,81
  • All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

    All kinds of translators, Guide , chartered private charter, photographers, business escorts, medical accompaniment, travel guides, customization throughout the United States

    From€ 13,24
  • Chicago: Premier Dinner Cruise on Lake Michigan

    Chicago: Premier Dinner Cruise on Lake Michigan

    Duration: 150 mins
    From€ 149,34
  • Big Bus Chicago: Hop-on Hop-off Bus Tour

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

    Duration: 2 hrs
    English
    From€ 38,12
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    From€ 83,86
  • Chicago: Canine Cruise

    Chicago: Canine Cruise

    Duration: 90 mins
    English
    From€ 35,58
  • Lake Michigan: Premier Brunch or Lunch Cruise

    Lake Michigan: Premier Brunch or Lunch Cruise

    Duration: 2 hrs
    From€ 103,03
  • Chicago: Guided Food Tasting + Bike Tour

    Chicago: Guided Food Tasting + Bike Tour

    Duration: 4 hrs
    English
    From€ 83,86
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    From€ 71,99
1
2
3

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: 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
UNIONPAYMCVISAAMEXJCBDINERSDISCOVERAPPLECOINSEGIFT
Our partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.