Bootleggers, Bullets & Baloney
The LoopCrime Tour

Bootleggers, Bullets & Baloney

2h9 stops~2.7 miles

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 Experience

What You'll Experience

2h
Walking time
9
Audio stops
~2.7mi
Walking distance
41+
Facts & fibs to sort

A taste of what you'll hear

9 stops, each with its own story. Here's a preview.

"You're standing near where the Lexington Hotel once stood. This was Al Capone's headquarters from 1928 until his arrest in 1931. The building is gone now—demolished in 1995—but for three years, this was the most dangerous address in America."

— The Site of the Lexington Hotel

"We're stepping away from Capone for a moment to talk about John Dillinger—a different kind of criminal entirely. Dillinger wasn't a mob boss. He was a bank robber. A celebrity bank robber."

— The Biograph Theater

"Alright, Bad Historians. You made it. You walked through Prohibition-era Chicago without getting shot, which is more than some people could say back then. Here's what was REAL: The tunnel under the Lexington? Real."

— The Reveal

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?

Download the app, head to the starting point, and press play. The stories start themselves.

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