Chicago Walking Prohibition Tour: Explore the City's Alcohol History
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Step back into Chicago’s past with the Walking Prohibition Tour and discover how the city’s streets buzzed with clandestine alcohol activity during Prohibition. From secret speakeasies to notorious gangster hideouts, this tour reveals the stories behind Chicago’s bootlegging era.
Learn about the rise of gangsters like Al Capone and the underground world they operated in. Visit historic sites that played a key role in the city’s alcohol smuggling and distribution network, gaining a deeper understanding of how Chicago navigated the challenges of Prohibition.
Whether you're a history buff or just curious about Chicago’s rebellious spirit, this tour offers a fascinating glimpse into a pivotal time in the city’s history. It’s a chance to see the city through the lens of its underground nightlife and criminal underworld.
Frequently asked questions
How long is the Walking Prohibition Tour?
The tour lasts approximately 3.5 hours.
What language is the tour conducted in?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 15 participants.
Is the tour suitable for children?
The tour is designed for adults aged 21 to 100. Infants and small children can ride in a pram or stroller.
Are food and drinks included?
No, all food and drinks are optional and paid for separately by guests.
Is the tour accessible for wheelchair users?
Yes, the tour is wheelchair accessible.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 3.5 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Expert Historical Information
Not included
- All food or drinks are optional and paid by the guests.
Itinerary
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Stop 1
Hear about the beginning of prohibition itself, what the speakeasy was and the rise of the gangsters inside a former Al Capone controlled location.
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Stop 2
A Chicago staple with a surprisingly deep connection to “The Outfit”. Here guests will learn more about the true scope of the Capone organization as well as prohibition’s ultimate failure and repeal.
Meeting point & pickup
Meet at the starting point
When you arrive, please go inside and tell the host you are with the Prohibition Tour.
Open in Google MapsHow to get there
Meet everyone at the start point.
Cancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day(s) before
- 0% refund if cancelled 0–1 day(s) before
Instant confirmation
Your booking is confirmed immediately after checkout.
From $45.00 per person
- Free cancellation
- Secure checkout with our booking partner
