From
$249 USDper person
Private Chicago Gangster and Prohibition History Tour
Discover Chicago's infamous gangster past on a private, fully customized tour of the city's historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary criminal events from the 1920s...
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Discover Chicago's infamous gangster past on a private, fully customized tour of the city's historic Prohibition-era streets. Travel in comfort with your English-speaking driver, who shares captivating stories about Al Capone, rival gangs, speakeasies, and legendary crime events from the 1920s and 1930s.
Start at the Biograph Theater, where John Dillinger was shot, then visit the site of the St. Valentine's Day Massacre, a pivotal moment in the rise of Al Capone.
Explore the Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray's Italian Steakhouse, all tied to Chicago's mob history. Conclude in the Chicago Loop, discovering hidden speakeasies and secret nightlife spots from the Prohibition era.
With a flexible door-to-door itinerary, this private tour offers an immersive and exciting look at the city's dramatic gangster history.
Included
- Hotel pickup and drop-off or customized.
- Professional local driver/informal English-speaking guide.
- Fuel and tolls
- All taxes and handling charges.
- Hotel pickup and drop-off.
- Wi-Fi on board
- Water
- Wi-Fi
Not included
- Food and drinks
- Tips and rewards
Your route
Explore each stopPickup or meeting point
Confirm the start location with the local team.
15-60 minutes
Confirm the start location with the local team.
Main activity
Enjoy the verified Proactivitis experience.
120-240 minutes
Enjoy the verified Proactivitis experience.
Return or closing
Finish with local coordination and support.
15-60 minutes
Finish with local coordination and support.
Departure and return arrangements
Arrive 15 minutes before the confirmed time and keep your phone available for WhatsApp updates.
At the end, the team confirms return, photos or any pending detail by WhatsApp.
Cancellation and terms
Free cancellation up to 24 hours before start. After that period, 100% of the reservation is charged.
Final pickup time, meeting point and operating order can change for weather, traffic, sea conditions or local safety instructions. The confirmed activity, core inclusions and support remain protected.
Logistics and requirements
Pickup
Pickup included depending on the hotel, accommodation or point confirmed in the reservation.
Meeting point
Chicago, United States
Physical level
Easy
Minimum age
3+
Participation requirements
Not wheelchair accessible Not suitable for pets Babies should not sit on laps. For 1-3 people: A comfortable sedan will be assigned to your group. For 4-7 people: A spacious minivan will be assigned to your group. Throughout your journey, our drivers act as informal local guides, sharing local stories, stories and tips at each stop. Please note that drivers cannot enter museums or archaeological areas, but they will ensure you make the most of your visit with suggestions and general information before exploring on your own. Please show this to your driver. Your driver will meet you at the selected pickup location and time and will wait up to 30 minutes after the scheduled pickup. If contact is not made within this time, the booking will be considered a no-show and the driver will be allowed to leave. Before your trip, you will receive your driver's name, phone number and vehicle details, so you can easily recognize them upon arrival. Your driver will be punctual, professional, and happy to help you with your luggage and any special requests before you begin your trip. Please note that this sightseeing tour cannot begin, end, or include stops at airports, ports, or train stations. If you have any special requirements, such as traveling with a service animal or need additional assistance, please mention this when booking to ensure a smooth and enjoyable experience. ACCESSIBLE STROLLER OR STROLLER NEARBY PUBLIC TRANSPORTATION BABY SEATS AVAILABLE
What to bring and advice
- ID
- Comfortable clothes
- Sunscreen
- Phone
- Schedule can change by local operation.
- Pickup details are confirmed before departure.
Frequently asked questions
How do I book Private Chicago Gangster and Prohibition History Tour?
Choose date, time, travelers and continue to secure checkout. You receive confirmation and WhatsApp support.
Is pickup included?
Pickup included depending on the hotel, accommodation or point confirmed in the reservation.
Can I cancel or change the date?
Free cancellation up to 24 hours before start. After that period, 100% of the reservation is charged.
What should I bring?
Bring ID, Comfortable clothes, Sunscreen, Phone and keep your phone available for coordination.
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