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Chicago: Roaring '20s, Art Deco, and Gangsters Walking Tour

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$35.00 /person
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About the activity

Step back in time with a historical walking tour of Downtown Chicago. Learn about the city's Roaring '20s era, hear stories about gangster Al Capone, and wander by Great-Gatsby-esque architecture.

  • Free cancellation
    Cancel up to 24 hours in advance for a full refund.
  • Instant confirmation & Mobile tickets
    Receive your ticket right away. Use your phone or print your voucher.
  • Live guiding
    English
  • Duration
    2 hours
  • Includes
    • Guide
    • Walking tour
    • Tips
Highlights & Description

Highlights

  • Feel your spine tingle with historical stories of gangsters and murderers
  • Step back in time to the Great Gatsby glamor of Chicago's roaring '20s
  • Learn unique historical facts and see examples of the Art Deco architectural style
  • Discuss the impact of the Great Economic Crash of 1929 in Chicago
  • Visit an underground, secret gangster headquarters, including a hidden vault

Description

Perfect for families, friends, or a combination of both, learn about the Windy City's glamorous 1920s era on a walking tour through Downtown Chicago. Visit Al Capone's favorite haunts, discover magnificent Art Deco buildings, and learn how the crash of '29 forever altered the city's economy.
Your tour begins with tales of the city's infamous gangster, Al Capone, boss of the Chicago Outfit and commonly referred to as Scarface. Visit some of the bars he was rumored to frequent, including several Art-Deco buildings with their sleek and geometric architectural designs.
Listen closely as your guide tells you the story of Leopold and Loeb, two wealthy students at the University of Chicago, who almost got away with what was dubbed as the "perfect murder." Walk further along the river to hear more tantalizing stories, including tales of the Great Crash of 1929.
Then it's time to head back downtown to visit an old gangster headquarters. Before ending your tour, feast your eyes on real photographs and newspapers from the 1920s or take a photo in front of an old uncovered vault.

Good to know before you go
  • This tour will take place rain or shine
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Frequently Asked Questions

1. What is the cancellation policy for this activity?
Cancel up to 24 hours in advance for a full refund.
2. When will I receive the confirmation of my booking?
You will receive an email notification right after your successful payment. If you don't see it in your inbox, check your spam or junk mail folder. When the payment is completed you have the option to download your ticket directly.
3. Are mobile tickets enough or do I have to print them?
Tickets don't need to be printed. You can show your ticket from your smartphone as a PDF.
  • Adults
    11-64 years
  • Seniors
    65-99 years
  • Children
    0-10 years
May 2025
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