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.
View in App — $9.99What You'll Experience
Plan your walk
Know the route before you buy
- Starts at
- The Site of the Lexington Hotel
- Ends at
- The Reveal
- Walking plan
- 2h at your own pace
- Schedule
- Start, pause, and resume anytime
Included in the app
- Professional narration
- GPS-triggered stops
- Downloadable tour audio
- Ask the Historian Q&A
- Optional end-of-tour reveal
- All 9 story stops
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."
"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."
"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."
Tour itinerary
Every stop on this walk
Explore the route before you go. Each stop has its own story preview, location details, and place in the larger tour.
- 1The Site of the Lexington Hotel Read this stop
- 2St. Valentine's Day Massacre Site Read this stop
- 3Holy Name Cathedral Read this stop
- 4The Green Mill Cocktail Lounge Read this stop
- 5The Biograph Theater Read this stop
- 6The Chicago Theatre Read this stop
- 7The Palmer House Hotel Read this stop
- 8The Site of the Metropole Hotel Read this stop
- 9The Reveal Read this stop
Stories first
Every stop is built around people, conflict, ambition, and consequences—not a plaque read aloud.
Most of it is true. The extra mischief is just a wink at the end, but the story is what carries the walk.
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.
Get the AppBefore you go
Quick answers
How much is this tour?
$9.99 as a one-time purchase in the iOS app. The Chicago city pack is $14.99 and includes every currently available tour in the city.
Can I use it with spotty cell service?
Download the tour audio on Wi-Fi before leaving. Cached narration plays without streaming; map tiles and other online features may still need a connection.
Do I have to start at a specific time?
No. Start when it suits you, pause for a detour or meal, and resume later. Check the opening hours of any venue you personally plan to enter.
Are admission tickets included?
The purchase covers the Bad Historian audio experience. Transportation, food, and admission to third-party attractions are not included.
Other Chicago Tours
Museum Campus
Museum Campus: Landfill of Dreams
The story of three world-class museums built on fifty-seven acres of garbage, one controversial stadium, and a midnight bulldozer raid.
The Loop
Steel, Stone, and Ego
After the Great Fire, Chicago handed the keys to a bunch of ambitious architects and said — fix this. What followed was a century of skyscrapers, scandals, and egos the size of the buildings themselves. You'll meet the man who invented "form follows function" and died broke, a political dynasty that turned one building into a fifty-times fortune, and an artist who REALLY wishes you'd stop calling his sculpture "the bean."
Lincoln Park
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.
Downtown
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.
One-time
$9.99