Chicago Gangster Tour by Bus: Prohibition Era Sites

An actor in a gangster persona walks you through the 1920s mob wars that shaped Chicago.

Chicago's Original Gangster Tour is a guided bus tour through Prohibition-era sites including the St. Valentine's Day Massacre location, Biograph Theater, and Holy Name Cathedral, led by an actor guide who takes on a gangster character. The tour runs roughly two hours and covers the exploits of Capone, Moran, Dillinger and other figures from the 1920s and 1930s. Reservations are strongly recommended.

Step-by-step itinerary

Explore Chicago's Prohibition Era sites

• Visit Biograph Theater site
• See Holy Name Cathedral

The experience

The tour departs as a bus ride through Chicago's streets, stopping at the actual locations where the city's most notorious mob figures operated and died. Your guide is an actor who performs as a gangster character, which means the history comes with personality and humor rather than a straightforward lecture. You'll see the Biograph Theater, where John Dillinger was killed, and Holy Name Cathedral, where the North Side Gang's Dean O'Banion (who ran a flower shop across the street that handled mob funerals) was murdered in 1924. The St. Valentine's Day Massacre site is also on the route, one of the most infamous moments in Chicago's gangster history.

What separates this from a standard historical tour is the guide's approach. The actor leans into the gangster persona and has fun with it, which keeps the material entertaining even as it covers real events from the Prohibition era. You're learning about Capone, Moran, Dillinger and the rest of the underworld figures who operated in Chicago during the 1920s and 1930s, but the delivery is theatrical rather than dry. The bus format means you're not walking long distances. You move between sites by vehicle and step out at each location to see it.

Raffles and prizes are included, adding another layer to the experience beyond the tour itself. The tour is suitable for all fitness levels since most of the time is spent on the bus or at brief stops. Service animals are welcome, and public transportation options are available near the tour's starting point if you need them. Book ahead: reservations are strongly recommended, as tours fill up.

What’s included

• The tour includes the bus ride to all sites.
• an actor guide performing as a gangster character.
• raffles and prizes during the experience.

Before you book

Days and timesThursday to SundayDepartures at 11:00 and 13:00

Book up to1h before

AgesAdult (10 and older) · Under 10: can't be booked

GroupUp to 10 · max 4 per booking

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled if the minimum number of travelers isn't reached. If that happens, you're offered another date or a refund.

Prices and times updated yesterday

Good to know

Low physical effortPets welcomePublic transport nearby

Operated by Untouchable Tour - Chicago's Original Gangster Tour

Is this one for you?Your gangster guide performs the era's history as you ride past the St. Valentine's Day Massacre, the Biograph Theater, and Holy Name Cathedral: covering major sites without the walking.

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Top questions

What exactly happened at the Biograph Theater that makes it part of this tour?

The Biograph Theater is where John Dillinger, one of the most wanted criminals of the Prohibition era, was killed. The tour stops there so you can see the actual site where this famous event took place.

Who was Dean O'Banion and why does the tour visit Holy Name Cathedral?

Dean O'Banion was a North Side Gang leader who was murdered in his flower shop across the street from Holy Name Cathedral in 1924. He was a choir boy there as a child, and his flower shop, Schofield's, handled all the flowers for mob funerals. The cathedral is a key location in Chicago's gangster history.

How long does the tour take?

The tour runs approximately two hours, covering multiple Prohibition-era sites by bus with stops at each location.

Is the guide a historian or an actor?

The guide is an actor who takes on a gangster character and persona for the tour. This theatrical approach makes the historical content entertaining while still covering real events from the 1920s and 1930s.

What's included in the tour price?

The tour includes the bus ride, the actor guide, access to all the sites, and raffles and prizes during the experience.

Do I need to be in good shape to do this tour?

No, the tour is suitable for all fitness levels. You spend most of the time on the bus, with brief stops at each location to see the sites.