Bootleggers, Bullets & Baloney
Walk through Prohibition-era Chicago, when this city was run by gangsters, corrupt politicians, and men with surprisingly good taste in suits. Everything I tell you will sound absolutely true. Some of it is. Some of it... I made up. Your job? Try to figure it out.
Start this tour freeWhat You'll Experience
Your Route
8 stops, each with its own story. The audio guides you from one to the next.
Part tour, part game
Most of what you hear is true. But we slip in a few things that aren't. At the end, there's a quiz — can you tell which facts were real?
It makes you pay attention. And it's way more fun than just listening.
Have questions? Just ask.
Curious about something you heard? Want to know more about a place? Ask us anything — we have a lot to say. It's more fun when it's a conversation.
Ready to Start?
Download the app, head to the starting point, and let the stories begin.
Start free in the appOther Chicago Tours
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Steel, Stone, and Ego
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The Best Free Day in Chicago
One of America's oldest free zoos. A Victorian glass house. A hidden garden designed by a man who cashed in his life insurance for flowers. And roughly twelve thousand unmarked graves. All free.
The Postcard Tour
Chicago's greatest hits — and the stories behind them. A river that flows backward, buildings covered in stolen rocks, towers that look like corn cobs, and a giant bean made by a man who wishes you'd stop calling it a bean.