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1920s Chicago Walking Tour: Art Deco, Flappers, Gangsters, and Prohibition

icon 2 hours Mobile ticket Free Cancellation
Tickets from € 33.72

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November 2024
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Discover Chicago of the Roaring '20s thru its Art Deco architecture! We all LOVE the elegance, glam, and glitz of the 1920s. This 2-hour walking tour explores the interiors and exteriors of gorgeous buildings from this surprisingly brief architectural period in Chicago, with some interesting details and stories about life in that era. Flappers, gangsters, jazz, speakeasies — we'll pepper those throughout our larger exploration of Chicago's magnificent Art Deco buildings in order to truly set the context for you! You’ll walk in the footsteps of those high on the potential of the future, before the infamous Crash of ‘29. In addition to experiencing magnificent Art Deco architectural interiors, you’ll also learn about Chicago’s notorious gangster history — even ending the tour inside an old gangster headquarters surrounded by real photographs, newspapers, and an old uncovered vault!
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  • Local guide
  • Gratuities
  • Hotel pickup and drop-off
Departure Point

125 S Clark St, Chicago, IL 60603, USA We meet directly in front of (outside) the entrance to Revival Food Hall.

Return Details

33 W Kinzie St, Chicago, IL 60654, USA We end inside an old mobster headquarters, where guests are encouraged to stay after the tour and grab a bite to eat!

  • Downtown / The Loop, Chicago, Illinois, United States
    The majority of this tour will happen Chicago's famous downtown district, "The Loop," where we will pop inside a few more stunning Art Deco buildings and learn about the style and the time.
    60 minutes
  • Chicago Riverwalk, Chicago, Illinois, United States
    We will admire some 1920s "building boom" skyscrapers as we make our way across the Chicago River.
    15 minutes
  • River North, Chicago, Illinois, United States
    We will end our 1920s walk inside a famous old mobster headquarters that's now a popular restaurant, where we will see old photos, newspapers, and more, and where guests can stay after the tour for special discounts on food and drinks!
    15 minutes
  • Infants and small children can ride in a pram or stroller
  • Service animals allowed
  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Travelers should have at least a moderate level of physical fitness
  • Operates in all weather conditions, please dress appropriately!
  • Regularly sanitized high-traffic areas
  • COVID-19 vaccination required for guides
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, cancel at least 24 hours before the scheduled departure time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
WorldlyMouse
24 Dec 2022
The guide was knowledgeable and conveyed the information clearly and interestingly Saw parts of Chicago in a new way or for the first time. I received an architecture degree from IIT and what I saw with guide fit into that view of the world plus expanded it.
lizmtraveler333
17 Dec 2022
Absolutely amazing tour! I was actually originally planning to do a different tour, but this was the one that happened to work with my schedule for the day, and it was a fantastic way to spend an afternoon. Haley was knowledgeable, friendly, and experienced, and I learned so much about art deco architecture and Chicago history. Many thanks to Haley for braving the cold, and I can't recommend this enough!
Stay812725
19 Nov 2022
The tour guide was very knowledgeable. The buildings selected were interesting. The amount of walking was perfect.
This tour in Chicago is organized by Inside Chicago Walking Tours

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We always double-check the availability with our local partners for each booking. Even though this is usually a swift process, it can take up to 24 hours. Once this process is completed you will receive your voucher or ticket by email. If our local partner is not able to confirm your booking we will offer you the best possible alternative. If the new date and/or time doesn’t fit your itinerary, we will reimburse the full amount paid.
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