Chicago Historical & Heritage Tours

Chicago Historical & Heritage Tours

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

5 star rating: Highly Recommended 54 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $26.00

Chicago Prohibition Tour

5 star rating: Highly Recommended 53 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 ...  Read more

Location: Chicago, Illinois
Duration: 3 hours 30 minutes

From USD $44.99

Chicago Crime and Mob Tour

4.5 star rating: Recommended 266 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 ...  Read more

Location: Chicago, Illinois
Duration: 90 minutes

From USD $35.95
$39.95 Save $4.00

Haunted Chicago Segway Tour

5 star rating: Highly Recommended 14 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $70.85

Chicago Walking Tour: Art Deco Skyscrapers

5 star rating: Highly Recommended 37 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 ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

Chicago Walking Tour: Historic Skyscrapers

5 star rating: Highly Recommended 32 Reviews

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

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

Chicago 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. ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $25.00

Chicago Walking Tour: Modern Architecture

5 star rating: Highly Recommended 8 Reviews

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

Location: Chicago, Illinois
Duration: 2 hours

From USD $18.00

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 ...  Read more

Location: Chicago, Illinois
Duration: 60 minutes

From USD $12.00

Telling the Story Walking Tour

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 $25.00

1950's Nightlife in the Loop Tour

4 star rating: Recommended 1 Review

Intelligent architecture tours of Chicago for intelligent adults, we combine serious history with entertaining immersion in the past.  Experience Chicago's ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $59.00

Auditorium Theatre Historic Tour

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 ...  Read more

Location: Chicago, Illinois
Duration: 60 minutes

From USD $12.00

The Loop and Chicago Riverwalk 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 ...  Read more

Location: Chicago, Illinois
Duration: 3 hours

From USD $25.00

Creating the Melting Pot Walking Tour

Though all of Chicago’s neighborhoods are, of course, culturally rich, the West Loop is perhaps the closest and most accessible to visitors who would ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

Rebuilding the Second City Walking Tour

River North, one of the oldest neighborhoods in Chicago, has experienced unparalleled evolution over the past 200 years – and Inside Chicago Walking ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $25.00

1960's Nightlife in the Gold Coast Tour

Your 2-hour tour will take you back in time to experience the Chicago of an earlier era. One of the most exciting eras to explore is the 1960s when Playboy was ...  Read more

Location: Chicago, Illinois
Duration: 2 hours

From USD $59.00

The Roaring Twenties Art Deco and Decadence Tour

Chicago is a hub of Art Deco architecture, style, and history, and on this evening walking tour, you’ll learn all about what life was like in the Windy City ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $59.00

Chicago Gangster Tour

1 star rating: I do not recommend this 2 Reviews

Chicago has a long history of organized crime and was famously home to the American mafia figure Al Capone. In 1850, Chicago had a population of 80,000 people, ...  Read more

Location: Chicago, Illinois
Duration: 2 hours 30 minutes

From USD $35.00
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