Best History & heritage in Chicago

Local Recommendations from our My Guide Chicago team

Book Top Experiences and Tours in Chicago:

If youʻre booking your trip to Chicago last minute, we have you covered. Below are some of the top tours and experiences!

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The Best of Chicago in 2H Walking Tour

1 Reviews

The Best of Chicago in 2H Walking Tour

Explore the best of Chicago's downtown in a 2 hours walking tour with a fun local guide, this area is famous for its bold architecture, museums and landmarks such as the Cloud Gate and the Riverwalk.

$40.00

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Chicago's Black American historical bus tour

Chicago Black American tour paired with historical site seeing and artifacts. A tour the family can all enjoy.

$80.00

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Chicago: Private 3-Hour Al Capone Gangster Tour

5 Reviews

Chicago: Private 3-Hour Al Capone Gangster Tour

Visit the notorious hangouts of John Dillinger, the Untouchables, and Al Capone with an expert historian as your guide. Chicago’s mob history has long been immortalized in popular media - embark on this Chicago gangster tour to learn the true story.

$880.00

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Chicago Downtown Highlights Private Walking Tour

Explore the vibrant city of Chicago on a private walking tour led by a knowledgeable local guide

$270.00

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Loop Architecture tour in Chicago

1 Reviews

Loop Architecture tour in Chicago

Join us on this unforgettable journey through Chicago’s architectural gems in the heart of the Loop.

$616.75

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Chicago: Ultimate City Attractions Bike Tour

20 Reviews

Chicago: Ultimate City Attractions Bike Tour

See world's most beautiful skyline and Chicago's lovely lakefront on a guided cycle through the green spaces and monuments of Millennium and Grant Parks, Museum Campus and Northerly Island. See why they say Chicago is "cooler by the lake."

$54.99

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Chicago River: Guided Sunset Cocktail & Architecture Tour

52 Reviews

Chicago River: Guided Sunset Cocktail & Architecture Tour

Climb aboard a 90 passenger historic riverboat & sip cocktails while cruising the Chicago River! Relax and learn about the history & architecture of the city via live narration with a drink in hand.

$59.00

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Chicago's Architecture: A Self-Guided Audio Walking Tour

Be blown away by the design stories that lie beneath the Windy City‘s surface. Experience the magic of GPS-playback on this immersive stroll through Chicago.

$19.99

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Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

2 Reviews

Chicago: Full Day Food Walking Tour + FREE Bike/Kayak Rental

Make the most of your day in Chicago by sampling Chicago's iconic style foods, seeing top attractions with a local, expert guide. Includes a FREE 2 hr bike or kayak rental to explore even more.

$99.99

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Chicago: Vice, Crime and Gangsters Self-Guided Audio Tour

6 Reviews

Chicago: Vice, Crime and Gangsters Self-Guided Audio Tour

Delve into Chicago’s crooked past with this self-guided audio tour. Experience the magic of GPS playback as you immerse yourself in the history of crime, gangsters, and vice in the notorious city.

$6.99

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Chicago River: Best 90-Min Architecture Boat Tour

Marvel at the magnificent architecture on the Chicago River with expert tour guides! All ages welcome.

$32.00

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Chicago: Underground Pedway & Downtown Secrets Walking Tour

130 Reviews

Chicago: Underground Pedway & Downtown Secrets Walking Tour

Explore downtown Chicago through its underground passageways, known as "The Pedway," accessing beautiful interiors from both above ground and below, with secrets along the way, on a walking tour.

$35.00

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