Step Back in Time with Chicago's Roaring 20’s Speakeasy Tour
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; mostly walking on paved city streets
Overview
Experience Chicago’s underground nightlife as it was in the 1920s with a guided speakeasy tour through hidden bars and historic neighborhoods. Discover secret passages and sip Prohibition-era cocktails while hearing the city's gangland stories.
Roaring 20’s Speakeasy Tour
3 Hours • Adults Only Pub Crawl!
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Adventure Photos
About This Adventure
Step back into the Roaring 20s with an exclusive adults-only pub crawl through Chicago! Discover the city's hidden gangster history, visit speakeasies, and explore crime scenes. This immersive experience combines fun and adventure as you hop on and off the bus, revealing a unique side of Chicago's past.
ADULTS ONLY! Experience Roaring 20's Chicago as we search the streets of the Windy City for the remnants of the 1920s with gangsters, bar stops, speakeasies, crime scenes, and more! This is a pub crawl so be prepared to get on and off the bus during the tour. Bring your ID and prepare to have fun on a side of Chicago that not everyone gets to see!
Duration
3 Hours
Meeting Location
600 NORTH CLARK STREET (Outside of McDonalds)
Adventure Tips
Book in advance
Tours fill quickly due to limited group sizes—reserve your spot at least a week ahead.
Dress for the era
Embrace the Roaring 20’s vibe with vintage-inspired attire to enhance your experience and photos.
Arrive on time
Tours start promptly at scheduled times; late arrivals may not be accommodated for safety and flow.
Drink responsibly
Enjoy cocktails responsibly, especially since this is an urban walking tour with several stops.
Local Insights
Wildlife
- Urban peregrine falcons nesting on nearby skyscrapers
- Migratory birds along Lake Michigan shore
History
Chicago’s speakeasy culture exploded in the 1920s, shaped by Prohibition laws and the infamous gangland wars involving figures like Al Capone.
Conservation
The tour emphasizes respecting historic sites and encourages walking or transit to reduce urban pollution impact.
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Adventure Hotspots in Chicago
Frequently Asked Questions
Recommended Gear
Comfortable walking shoes
The tour involves several blocks of urban walking on pavement.
Light jacket
Chicago evenings can get chilly—dress in layers during fall tours.
fall specific
Portable phone charger
Capture photos and ensure your phone lasts through the tour.
Photo ID
Required for age verification when ordering cocktails at speakeasies.