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Top Picks for Chicago Tours

Discover 94 Tours in Chicago on Trip.com, updated September 18, 2025, with experiences lasting from 1 to 9 hours. Find the perfect adventure for your day!

From GBP 7.32 per person, with an average total of GBP 47.00. Choose the option that suits your plan.

Now on Trip.com: "Chicago: Food and Prohibition Architecture Guided Tour", a 5-hour adventure in Chicago!

The next available day tour departs on September 19, 2025. Book now to secure your spot!

Chicago Tours usually take about 5 hours — perfect for a relaxed, immersive experience!

100% of Chicago Tours now offer English-speaking guides

September is the perfect time to visit Chicago! Choose from Tours available day tours, including seasonal favorites like Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929.

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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94 Results for Chicago Tours

  • Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Chicago architectural sightseeing cruise (departing from Michigan Avenue or Navy Pier) 83929

    Duration: 1 hr
    English
    From£36.61
  • Signature dishes of Chicago bike tour

    Signature dishes of Chicago bike tour

    󱩳Ride around Chicago as you listen to an expert guide
    English
    From£65.91
  • Chicago: Guided Food Tour + Bike or Kayak Rental

    Chicago: Guided Food Tour + Bike or Kayak Rental

    Duration: 150 mins
    English
    From£62.27
  • Chicago: Food and Prohibition Architecture Guided Tour

    Chicago: Food and Prohibition Architecture Guided Tour

    Duration: 5 hrs
    English
    From£72.53
  • Chicago: Chinatown Food & Culture Walking Tour

    Chicago: Chinatown Food & Culture Walking Tour

    Duration: 3 hrs
    English
    From£58.61
  • Chicago: Family & Food Guided Bike Tour

    Chicago: Family & Food Guided Bike Tour

    Duration: 4 hrs
    English
    From£58.61
  • Chicago Bus Tour: 90-Min Sunset Tour

    Chicago Bus Tour: 90-Min Sunset Tour

    Duration: 90 mins
    English
    From£36.13
  • Chicago lakefront neighbourhood bike tour

    Chicago lakefront neighbourhood bike tour

    󱩳Enjoy one of the most popular bike tours Chicago has to offer
    English
    From£7.32
  • Chicago: Food Tour + Bike or Kayak Rental

    Chicago: Food Tour + Bike or Kayak Rental

    Duration: 5 hrs
    English
    From£79.97
  • Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    Chicago Film and Television Tour: Skyscraper Fantasy Light and one-day tour

    󱩳Today you will step into the prototype streets of Gotham City in "Batman: The Dark Knight" and feel the mystery and coldness under the Gothic architecture.
    Duration: 3 hrs
    English
    From£91.96
  • Ultimate city bike tour in Chicago

    Ultimate city bike tour in Chicago

    󱩳Spot all of Chicago's top sights on a guided bike tour
    English
    From£8.05
  • Chicago Round-trip |Dubuque Town + Galena Town

    Chicago Round-trip |Dubuque Town + Galena Town

    󱩳Travel through Iowa's historic towns and enjoy the charming riverside scenery.
    Duration: 9 hrs
    English
    From£79.75
  • Chicago: Creepy Cruise

    Chicago: Creepy Cruise

    English
    From£30.96
  • Chicago: Culture & Architecture Guided Tour

    Chicago: Culture & Architecture Guided Tour

    Duration: 150 mins
    English
    From£35.90
  • Chicago: Highlights & Attractions Walking Tour

    Chicago: Highlights & Attractions Walking Tour

    Duration: 2 hrs
    English
    From£36.34
  • Hidden In Plain Sight: Chicago Prohibition Tour

    Hidden In Plain Sight: Chicago Prohibition Tour

    Duration: 210 mins
    English
    From£32.97
  • Chicago: Guided Haunted Tour

    Chicago: Guided Haunted Tour

    Duration: 1 hr
    English
    From£19.17
  • Original Chicago Prohibition Tour

    Original Chicago Prohibition Tour

    Duration: 4 hrs
    English
    From£40.30
  • Chicago Downtown: 3-Hr Guided Pizza Tour

    Chicago Downtown: 3-Hr Guided Pizza Tour

    Duration: 3 hrs
    English
    From£50.56
  • Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters

    Chicago Crime & Mob Bus Tour: Criminals, Mobsters and Gangsters

    Duration: 2 hrs
    English
    From£36.12
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