2-Hour Chicago Prohibition Gangster Bus Tour
Ride Chicago’s 1920s–30s gangster trail with actor guides
Duration
2 Hours
Includes
Gangster guide, Bus tour
Highlights
Explore Chicago’s Prohibition-era stories on a bus tour led by actor “Gangster Guides.” You’ll stay on the bus as your guide shares historic accounts and points out key city sites.
- Hear stories from the 1920s and 1930s, including Prohibition
- Visit sites tied to Capone, Moran, and Dillinger
- See the St. Valentine’s Day Massacre location
- Pass the Biograph Theatre and Holy Name Cathedral
- Meet at 600 N Clark St by the McDonald’s between Ohio and Ontario
- Stay on the bus for the full 1 hour 40 minutes to 2 hours
Things to know
No coolers, alcohol, or food allowed on the bus. Non-alcoholic beverages with a lid are welcome.
Cancellation Policy
All sales are final after your credit card has been processed. We do not offer refunds, adjustments, or exchanges for another tour time. All tours depart at the scheduled time.
FAQs
Meet at the intersection of Clark & Ohio (600 North Clark Street), on the Clark Street curb in front of the McDonald’s.
The tour lasts 1 hour 40 minutes to 2 hours, and guests remain on the bus for the duration.
No coolers, alcohol or food are allowed on the bus. Non-alcoholic beverages with a lid are welcome.
More about Holy Name Cathedral
Holy Name Cathedral rises from the corner of State and Superior in Chicago's River North, a Gothic Revival landmark whose limestone spires have witnessed more than a century of the city's most dramatic moments. While today it serves as the seat of the Archdiocese of Chicago, Holy Name Cathedral holds a darker claim to fame that makes it an unforgettable stop on Chicago's Original Gangster Tour. The sidewalks surrounding the cathedral were the stage for two of the most notorious mob hits of the Prohibition era, forever linking this sacred space to the bloody chess game between Al Capone's South Side Outfit and Dion O'Banion's North Side Gang.
As the tour pulls up to Holy Name Cathedral, you will hear the story of Dion O'Banion, the florist-turned-bootlegger whose flower shop sat directly across the street. It was there, in November 1924, that O'Banion was gunned down by Capone's men in a handshake-turned-ambush that ignited Chicago's bloodiest gang war. Three years later, his successor Hymie Weiss was cut down by machine gun fire on the cathedral steps themselves, and guides will point out the stonework that still bears the legend of those bullet scars. Standing on that very sidewalk, with traffic humming past and the cathedral bells overhead, the contrast between the soaring sanctuary above and the violent history below becomes strikingly real.
Holy Name Cathedral is a must for history buffs, true crime fans, and curious travelers who want their Chicago sightseeing to dig beneath the postcard skyline. Families with older kids fascinated by the Roaring Twenties will find the storytelling vivid without being gratuitous, and anyone who has watched a gangster film will recognize names and rivalries that shaped the entire genre. Pairing one of Chicago's grandest houses of worship with one of its most infamous crime scenes, Holy Name Cathedral captures the city's contradictions in a single, unforgettable stop.