Bootleggers, Bullets & Baloney
Al Capone ran a hundred-million-dollar beer empire, bathed three times a day, and lost it all to a tax form. A singer got his throat cut for switching nightclubs. A bank robber broke out of jail with a pistol carved from wood. Walk Prohibition-era Chicago from the Green Mill — where you can still drink in Capone's booth — down to the vanished hotels of the South Side, past the massacre site that's now a lawn and the cathedral where a man was gunned down in daylight. Most of it is documented. A few small things I slipped in myself. See if you can spot them before the reveal.
What You'll Experience
Plan your walk
Know the route before you buy
- Starts at
- Introduction
- Ends at
- The Reveal
- Walking plan
- 35 min 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 10 story stops
A taste of what you'll hear
10 stops, each with its own story. Here's a preview.
"For about thirteen years, this was the most dangerous well-dressed city on Earth. Chicago during Prohibition. The booze was illegal, the mayor was on the payroll, and everybody was drinking while loudly disapproving of drinking."
"That six-story vertical sign spelling out the city's name is probably the single most photographed object in Chicago. It went up in nineteen twenty-one on a movie palace built to make ordinary people feel like royalty for the price of a ticket."
"Alright. You walked all the way through Prohibition Chicago and nobody put fourteen bullets in you, which puts you ahead of several people in this tour. Let's settle up. Time for me to point out which details were mine."
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.
- 11IntroductionFor about thirteen years, this was the most dangerous well-dressed city on Earth. Chicago during Prohibition.41.9686, -87.6529 Read this stop
- 22The Green Mill Cocktail LoungeThe Green Mill. That crescent-moon sign has been hanging over this corner since nineteen ten, and the room behind it has barely changed.41.9686, -87.6529 Read this stop
- 33The Biograph TheaterThe Biograph, and its restored marquee, look frozen in the summer of nineteen thirty-four. That's deliberate, and there's a reason.41.9257, -87.6495 Read this stop
- 44The St. Valentine's Day Massacre SiteYou're looking at a strip of lawn and a parking lot. Some grass, a few trees, cars. It is one of the most infamous addresses in American...41.9137, -87.6362 Read this stop
- 55Holy Name CathedralLook up. Holy Name Cathedral — the seat of the whole Chicago archdiocese, and one of the most beautiful buildings in the city.41.8956, -87.6304 Read this stop
- 66The Chicago TheatreThat six-story vertical sign spelling out the city's name is probably the single most photographed object in Chicago.41.8854, -87.6276 Read this stop
- 77The Palmer House HotelThe Palmer House. There has been a hotel on this spot since eighteen seventy-one, which makes it the longest continuously operating hotel in...41.8800, -87.6277 Read this stop
- 88The Site of the Lexington HotelThere is no building to point at here. The Lexington Hotel came down in nineteen ninety-five, so if you're hunting for something grand, I'm...41.8721, -87.6246 Read this stop
- 99The Site of the Metropole HotelAnother gap in the block. Another Michigan Avenue hotel that isn't here anymore. The Metropole is where Capone set up before the Lexington,...41.8745, -87.6246 Read this stop
- 1010The RevealAlright. You walked all the way through Prohibition Chicago and nobody put fourteen bullets in you, which puts you ahead of several people...41.8745, -87.6246 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
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Everything on this campus stands on ground Chicago manufactured out of a burned-down city. A marble temple holds the most complete Tyrannosaurus rex on Earth, found because somebody got a flat tire. An aquarium a thousand miles from the sea got filled by hauling a million gallons of ocean up from Key West in railroad tank cars. There's the first planetarium in the Western Hemisphere, a two-thousand-year-old Roman column Mussolini sent as a thank-you gift, and a downtown airport a mayor erased with bulldozers at one in the morning. Walk the lakefront from Buckingham Fountain to Soldier Field. Nearly all of it is documented. A few small things I mixed into the fill myself. See how many seams you can find before I show you.
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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.
Bootleggers, Bullets & Baloney
$9.99 · one-time