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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

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!

City: Chicago

Sun 23 Feb

Other dates

You can choose the date already on the booking website

Starting at $35.00

Make a reservation

Sun 23 Feb

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!
Regularly sanitised high-traffic areas
COVID-19 vaccination required for guides

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 few more stunning Art Deco buildings and learn about the style and the time.

Chicago Riverwalk

We will admire some 1920s "building boom" skyscrapers as we make our way across the Chicago River.

River North

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!

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (27)

Stay812725

Nov 2022

The tour guide was very knowledgeable. The buildings selected were interesting. The amount of walking was perfect.

KarenA498

Oct 2022

Our tour was actually titled gangsters and ghosts and this is mainly what was covered. The tour guide was excellent and even though it was cold and raining he made the best of shelter around the route. We learnt a lot about 1920s Chicago.

PeggyHelling

Aug 2022

Kylie was A++++ guide! The tour sped by because she was so knowledgeable and interesting. Loved every stop and felt it was the perfect tour after the Riverboat. The interiors were truly amazing!