ChicagoExperiences
ChicagoExperiences

Top Picks for Chicago Experiences

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.

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45 Results for Chicago Experiences

  • 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· 40 booked
    From
  • 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
  • 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
  • Chicago Full Day Bike Rental

    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

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

    Duration: 90 mins
    From
  • Chicago Seadog: Lakefront Speedboat Tour

    Chicago Seadog: Lakefront Speedboat Tour

    Duration: 30 mins
    From
  • Lake Michigan & Chicago River: 75 Minute Speedboat Cruise

    Lake Michigan & Chicago River: 75 Minute Speedboat Cruise

    Duration: 75 mins
    English
    From
  • Chicago: Premier Dinner Cruise on Lake Michigan

    Chicago: Premier Dinner Cruise on Lake Michigan

    Duration: 150 mins
    From
  • Big Bus Chicago: Hop-on Hop-off Bus Tour

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

    Duration: 2 hrs
    English
    From
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    From
  • Chicago: Skyline Lake Tour

    Chicago: Skyline Lake Tour

    Duration: 45 mins
    English
    From
  • Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch

    Lake Michigan Chicago: 2-Hr Sightseeing Cruise with Lunch

    Duration: 2 hrs
    From
  • Lake Michigan: Premier Brunch or Lunch Cruise

    Lake Michigan: Premier Brunch or Lunch Cruise

    Duration: 2 hrs
    From
  • Chicago Loop District Food Tour with Deep Dish & Beef Sandwich

    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

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    From
  • Chicago: Guided Food Tasting + Bike Tour

    Chicago: Guided Food Tasting + Bike Tour

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

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    From
  • Chicago: Family & Food Guided Bike Tour

    Chicago: Family & Food Guided Bike Tour

    Duration: 4 hrs
    English
    From
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    From
  • 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· 83 reviews
    From
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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:-)
Contact Center <br>of the year 2024
Contact Center
of the year 2024
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