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

Overview
Chicago is the birthplace of the skyscraper: imagine what incredible stories of engineering feats it has to tell!

Join Inside Chicago Walking Tours on our newest route — it’s Chicago’s ONLY engineering-themed tour! You’ll cover more than 150 years of engineering evolution, learning from a real engineer who makes the information accessible and graspable without ever dumbing it down. We believe that everyone can understand and be fascinated by these concepts if taught in an engaging and fun way.

You’ll see a building from the “father of the skyscraper,” who was actually an engineer and a classmate of Gustav Eiffel. You’ll learn how a “haunted” building gets its reputation simply by settling unevenly on its “floating” foundation. You’ll marvel at how Chicago’s buildings handle gravity and wind.

And as on all of our tours, you’ll visit the interiors of a few buildings to truly get that sense that you’ve seen inside Chicago!
City: Chicago
Fri 10 Oct
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You can choose the date already on the booking website
Starting at $35.00
Fri 10 Oct
Starting at $35.00
Make a reservation
What's Included
Local guide
Additional Info
  • 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!
What To Expect
1
Downtown / The Loop
The majority of this tour will happen Chicago's famous downtown district, "The Loop," where we will pop inside a couple buildings notable for their structural design.
2
Chicago Riverwalk
We will explore some more recent engineering feats along the Chicago River, with beautiful views!
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Traveler Photos
Reviews (40)
MichaelB332
Dec 2023
Our 2nd tour with this company and both have been fantastic. A must see tour for those Interested in Architecture and History. We took the Art Deco tour and saw spaces that we never thought to pop in.oum.
oboeadam
Jun 2023
Even though I've lived in Chicago for 3 years now, it's always fun to learn new and exciting things about this city. This tour actually takes you inside some of Chicago's most iconic buildings, as well as into some formerly secret places used by famous gangsters. Haley was a wonderful tour guide! She was knowledgable, personable, and attentive to all of us on the tour.
41samush
Jun 2023
Our guide Haley was knowledgeable, personable, and was able to facilitate fun connections between the members of the tour. This is clearly a passion for her, and she was able to instill that passion in all of us as we explored. This is our second tour with this company, and I cannot recommend it enough. Inside Chicago Walking Tours boasts a tour model that gets beneath surface facts, and shares the true beauty of our city and its rich history; these people are not tour guides - they are storytellers. Can't recommend this enough. We will be exhausting their list of tours whenever we have company in town!

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