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

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

Sun 02 Nov

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Sun 02 Nov

Starting at $35.00

Make a reservation

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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

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.

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)

Evgueni I

Dec 2024

We spent 2 very interesting and enjoyable hours with Henry. He made the experience very informative, enjoyable and added a lot of additional insights from own experience as a structural engineering specialist participating on number of building developments we saw. I wholeheartedly recommend this tour and our guide. There is a lot you do not see that’s worth discovering. Thank you, Henry!

J9881QEkenb

Mar 2024

I have to go on this tour again!! Yes! the modern era's glass and steel tallboys kiss the sky, but my personal favorites are the masterpieces built in the 1920s and 30s. If you have yet to visit the lobbies of these Art Deco treasures, you don't know what you are missing. A luxurious craftsmanship from an era gone by. This tour provides access that might prove difficult if you were to try on your own. I believe our tour guide's name was Hillary. Her knowledge and skill as a storyteller were matched by her passion and love of Chicago. Hillary has also perfected the art of silence. At just the right time, she allowed the beauty of these Art Deco masterpieces the chance to speak for themselves. I am grateful for what I learned, but more so for how I felt, surrounded by beauty and greatness. Our tour was attended by people who call Chicago home, and those visiting from other states and a few from overseas. Judging from the reactions of those visiting our city for the first time, I am convinced they will look back on this tour as the highlight of their visit. No doubt about it, I have to attend this tour again. A thank you and my strongest recommendations for Inside Chicago Walking Tours.

Lamyin

Mar 2024

Colleen was very professional. The walk was organized and informative. I appreciate her providing me with a good quality hearing device so that I don't miss any of her narrative. We were a 3 generation group and none of the kids, age 13, 11 and 7, complained. So you can take the whole family.