Chicago Gangsters and Prohibition Private History Tour
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Step into Chicago’s notorious gangster history with a private tour that takes you through the city’s Prohibition-era streets. Your English-speaking driver will share gripping stories about Al Capone, rival gangs, and legendary crime events from the 1920s and 1930s. This personalized experience offers a deep dive into Chicago’s dark past, all in the comfort of a private vehicle.
Begin your journey at the Biograph Theater, where John Dillinger was famously shot, then visit the site of the St. Valentine’s Day Massacre—one of the most shocking moments in organized crime history. From there, explore iconic locations like Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, each linked to Chicago’s mob past.
Wrap up your tour in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private experience offers an immersive and thrilling look into the city’s gangster history that’s perfect for history buffs and curious travelers alike.
Frequently asked questions
How long does the Chicago Gangsters and Prohibition Private History Tour last?
The tour lasts approximately 2 hours, giving you ample time to explore key sites and hear their stories.
What’s included in the tour?
Your package includes hotel pickup and drop-off, fuel and tolls, water, WiFi on board, a professional English-speaking driver, and all taxes and handling charges.
Can I customize the tour or choose specific stops?
Since this is a private tour, your driver can accommodate your interests and may adjust the itinerary within the available stops for a more personalized experience.
Is this tour suitable for children?
Yes, infants and small children can ride in a pram or stroller, and the tour is suitable for all physical fitness levels.
What should I do if I need to cancel?
You can cancel for a full refund if you do so at least 24 hours before the scheduled departure. Cancellations made less than 24 hours in advance are non-refundable.
Free cancellation
Full refunds are available if you cancel at least 24 hours before the scheduled departure.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Hotel pickup and drop-off
- Fuel and tolls
- Water
- WiFi on board
- Hotel or custom pickup and drop-off
- Professional English-speaking driver/guide
- All taxes and handling charges
Not included
- Meals and beverages
- Tips and gratuities
Itinerary
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Stop 1
The historic Biograph Theater is best known as the location where famous gangster John Dillinger was killed by FBI agents in 1934. The dramatic shootout occurred just outside the theater after he attended a movie screening. The building remains a key landmark linked to Chicago’s criminal past, symbolizing the turbulent Prohibition era.
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Stop 2
St. Valentine’s Day Massacre Site. This location marks the scene of the infamous 1929 massacre, where seven members of a rival gang were executed. Widely attributed to Al Capone’s empire, this brutal event shocked the nation and intensified efforts to fight organized crime. Today, it stands as a powerful reminder of Chicago’s gangster history.
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Stop 3
Holy Name Cathedral. This major religious site was the target of a 1926 drive-by shooting attempt on Al Capone, who narrowly escaped. The attack highlights the violent conflicts of Chicago’s mob era. The cathedral remains a significant landmark, blending spiritual and historical importance.
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Stop 4
Cook County Criminal Court Building. This courthouse was central to Chicago’s fight against organized crime, where many mobsters faced trial. Its history reflects the city’s long struggle to restore law and order during Prohibition.
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Stop 5
Harry Caray’s Italian Steakhouse (Former Mob Hangout). Located in a building once linked to Chicago’s criminal underworld, this restaurant’s past includes serving as a secret meeting spot during Prohibition. Today, it’s a popular dining spot that preserves its intriguing history.
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Stop 6
Chicago Loop Prohibition-Era Locations. Explore the streets where hidden speakeasies once operated, serving illegal alcohol during Prohibition. These secret venues played a vital role in Chicago’s nightlife, and walking through the Loop reveals the hidden world of the city’s gangster era.
Meeting point & pickup
Hotel pickup included for all travelers
Your driver will meet you at your chosen location and wait up to 30 minutes after the scheduled pickup time. You will receive driver details beforehand for easy recognition. The driver will assist with luggage and any special requests. Note that pickups do not include airports, ports, or train stations.
Open in Google MapsHow to get there
Pickup is available from 182 listed hotels. Exact pickup time will be confirmed after booking.
Cancellation & confirmation
Free cancellation
Full refunds are available if you cancel at least 24 hours before the scheduled departure.
- 100% refund if canceled at least 24 hours in advance
- No refund if canceled within 24 hours
- Cancellations may be affected by weather conditions
Instant confirmation
Your booking is confirmed immediately after checkout.
From $114.05 per person
- Free cancellation
- Secure checkout with our booking partner
