Chicago's Original Gangster Tour by Bus – Prohibition Era Adventure
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Step back into Chicago's Prohibition Era with Chicago's Original Gangster Tour by Bus. Our guides bring the 1920s and 1930s to life, sharing the real stories behind infamous figures like Al Capone, Bugs Moran, and John Dillinger. As you cruise through the city, you'll visit historic sites linked to these legendary gangsters and learn about their daring exploits.
What makes this tour stand out? Our Gangster Guides are actors who take on the personas of Chicago's most notorious criminals, making the experience both educational and highly entertaining. You'll hear about the St. Valentine's Day Massacre, see the Biograph Theater, and explore Holy Name Cathedral, all while enjoying a lively storytelling style.
Perfect for history buffs and curious visitors alike, this tour offers a fun and immersive way to discover Chicago's colorful past. Reservations are highly recommended to secure your spot on this popular adventure.
Frequently asked questions
How long is the Chicago's Original Gangster Tour?
The tour lasts approximately 1 hour and 45 minutes.
Is the tour suitable for children?
Yes, the tour is suitable for ages 10 and up, making it great for families and groups of adults.
What languages are available for the tour?
The tour is conducted in English.
Are the guides really actors?
Yes, our Gangster Guides are actors who adopt the personas of Chicago's notorious gangsters for a more engaging experience.
Is the tour accessible for all physical fitness levels?
Absolutely, the tour is suitable for all physical fitness levels.
Can I cancel my reservation if I change my mind?
Yes, you can cancel for a full refund if you do so at least 24 hours before the scheduled departure.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 1 hour 45 min
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Raffles and Prizes
Itinerary
Explore Chicago's gangster history with stops at key sites linked to legendary criminals, including the spot where John Dillinger was killed and the historic site of Dean O'Banion's murder.
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Stop 1
See the site where John Dillinger was killed.
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Stop 2
Visit the famous cathedral where Dean O'Banion was once a choir boy, and learn about his connection to the mob through his flower shop across the street, where he was killed in 1924.
Meeting point & pickup
Meet at the starting point
Meet the Gangster Guides at 600 N Clark Street (on Clark between Ohio and Ontario) outside the McDonald's.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 0–1 day
- Tour may be canceled if there are not enough travelers
Instant confirmation
Your booking is confirmed immediately after checkout.
From $48.00 per person
- Free cancellation
- Secure checkout with our booking partner
