Page 2 - Best Tours 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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Chicago: Architecture Center Cruise on Chicago's First Lady

143 Reviews

Chicago: Architecture Center Cruise on Chicago's First Lady

Experience a Chicago River cruise partnered with the world-famous Chicago Architecture Center, featuring live English-speaking certified docents and pre-recorded multilingual commentary.

$54.00

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Chicago: Malt Row Walking Brewery Tour

Discover the Malt Row in the Ravenswood Neighborhood of Chicago on a walking brewery tour. Visit three breweries and enjoy reserved seating and exclusive discounts at most of the tour stops.

$30.00

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Chicago: Evolution of the Skyscraper Walking Tour

8 Reviews

Chicago: Evolution of the Skyscraper Walking Tour

Chicago built some of the world’s first skyscrapers, with changing designs and technologies over time. Explore how these major developments came about, with examples from classic buildings to super-tall highrises from 1872 to the present.

$30.00

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Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

4 Reviews

Chicago: Christmas Eve Gourmet Dinner Cruise Lake Michigan

Celebrate Christmas Eve on a cruise on Lake Michigan aboard the Odyssey. Savor a delicious holiday 3-course plated meal served at your private table with a live onboard DJ.

$184.13

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Chicago: Art Deco Skyscrapers Walking Tour

19 Reviews

Chicago: Art Deco Skyscrapers Walking Tour

Art Deco's lavish materials and geometric ornament epitomized the prosperity and optimism of the Roaring 20s. Learn the history and characteristics of this modern decorative style while touring some of the city's most beautiful skyscrapers.

$30.00

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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's Modern Skyscrapers Guided Walking Tour

5 Reviews

Chicago's Modern Skyscrapers Guided Walking Tour

Chicago is recognized as a leader in Modern architecture, a style that revolutionized the visual world during the mid-20th century. Learn how Chicago developed the skeleton frame Modern skyscraper and gain insights into iconic Modernist Chicago buildings.

$30.00

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Chicago: Fireworks Cruise with Lake or River Viewing Options

248 Reviews

Chicago: Fireworks Cruise with Lake or River Viewing Options

Get up-close and personal to the epic Navy Pier fireworks display every Wednesday & Saturday during the Summer. Choose between viewing from either the Chicago River or Lake Michigan.

$28.00

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Chicago Historic Pullman Company Town Private Walking Tour

Take a trip by train out of Chicago to America’s first company owned town 'Pullman' and now a National Monument.

$270.00

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Chicago: Ultimate Food Walking Tour with Tastings

42 Reviews

Chicago: Ultimate Food Walking Tour with Tastings

Join the ultimate foodie adventure in Chicago with a food and tasting walking tour. Explore from deep-dish pizza to Chicago-style hot dogs and get the insider's take on the city’s culinary history.

$63.75

~~From $75.00~~

Philly's Architectural Wonders: A Self-Guided Audio Tour

Travel by your own rules using the self-guided audio tour and explore Philadelphia

$10.88

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Chicago Loop Architecture Private Walking Tour

Explore Chicago's rich architectural history on a captivating tour through the historic Loop District.

$227.00

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