Top Chicago Historical & Heritage Tours

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Chicago Prohibition Tour

5 star rating: Highly Recommended 103 Reviews

Discover the underground world of the Prohibition-era speakeasy on an entertaining adults-only tour that takes you to four historic Chicago bars. Learn why the ... 

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $45.00

Chicago Crime and Mob Tour

4.5 star rating: Recommended 369 Reviews

Some of the world’s most notorious criminals, mobsters and gangsters bamboozled their way through Chicago. On this Chicago crime tour, escape into the city’s ... 

Location: Chicago, Illinois
Duration: 90 minutes

From USD $39.95

Chicago Walking Tour: Interior Architecture of the Loop and Pedway Tour

5 star rating: Highly Recommended 93 Reviews

Get an in-depth look at Chicago Loop architecture on a walking tour that takes you inside landmark buildings in the design-rich city. Appreciate the interiors ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Chicago Walking Tour: Modern Architecture

5 star rating: Highly Recommended 10 Reviews

Explore Chicago's international, modern and postmodern movements, from the powerful, minimalist work of Mies van der Rohe's to contemporary styles that ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $20.00

Chicago Walking Tour: Art Deco Skyscrapers

5 star rating: Highly Recommended 41 Reviews

Discover the opulent exteriors and interiors of the Roaring '20s Jazz Deco and the classic finishes of Art Moderne buildings in this 2 hour tour. Learn of ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $20.00

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 41 Reviews

Perhaps Chicago's most identifiable claim to fame resides in its architecture. The prototype of the modern industrial metropolis arose from the charred ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $20.00

Chicago Architecture Walking Tour: Historical Masterpieces of the Loop

5 star rating: Highly Recommended 2 Reviews

Explore Chicago by walking through the foundations of modern architecture itself, from the "Father of the Skyscraper" to Chicago's very own style.

Location: Chicago, Illinois
Duration: 2 hours

From USD $30.00

Auditorium Theatre Historic Tour

5 star rating: Highly Recommended 1 Review

Go behind the scenes of this National Historic Landmark, built by Dankmar Adler and Louis Sullivan, and view it as few do in this one hour tour. Enjoy the ... 

Location: Chicago, Illinois
Duration: 60 minutes

From USD $12.00

Pullman National Monument Bus Tour

Step back in time and explore with us one this exclusive bus tour one of America's truly unique enclaves. The Pullman District is located on Chicago's far ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $35.00

Chicago History and Architecture Tour

Chicago’s iconic downtown is famous for its soaring skyscrapers, meandering river and impressive architecture. On this 3-hour walking tour of the Loop and the ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $25.00

Chicago's Best History and Riverwalk Tour

5 star rating: Highly Recommended 7 Reviews

On this fun and fascinating walking tour, learn about how Chicago grew from swampland bordering Lake Michigan into the thriving metropolis that it is today. ... 

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

Macy's State Street Historical Store Tour

Experience a historic store tour of Macy’s on State Street and learn how Macy’s has become America’s largest department store, with over 800 locations and more ... 

Location: Chicago, Illinois
Duration: 60 minutes

From USD $12.00

World's Fair Bus Tour

Relive the grandeur and magic of Chicago's two world's fairs on this one-of-a-kind bus tour that is the only tour in the city that recreates both fairs for ... 

Location: Chicago, Illinois
Duration: 3 hours

From USD $35.00

Haunted Chicago Segway Tour

5 star rating: Highly Recommended 15 Reviews

Learn about Chicago’s haunted past and see its mysterious sights as you glide through the city on a Segway at night! Venture through the dark with your ... 

Location: Chicago, Illinois
Duration: 2 hours

From USD $70.85
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