Chicago Gangsters and Prohibition Private History Tour
Overview
Discover Chicago’s infamous gangster past on a private, fully personalized tour through 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 of the 1920s and 1930s.
Begin at Biograph Theater, where John Dillinger was shot, then visit the St. Valentine’s Day Massacre site, a pivotal moment in Al Capone’s rise. Explore Holy Name Cathedral, the Cook County Criminal Court Building, and Harry Caray’s Italian Steakhouse, all linked to Chicago’s mob history.
Conclude in the Chicago Loop, uncovering hidden speakeasies and secret nightlife spots from the Prohibition era. With a flexible, door-to-door itinerary, this private tour offers an immersive, thrilling look into the city’s dramatic gangster history.
What's Included
- Hotel pickup and drop-off
- Fuel and Tolls
- Water
- WiFi on board
- Hotel or custom pickup and drop-off
- All taxes and handling charges
- Professional English-speaking local driver/informal guide
- Meals and beverages
- Tips and Gratuities
Meeting and Pickup
Your driver will meet you at the selected pickup location and time, and will wait for up to 30 minutes after the scheduled pickup. If no contact is made within this time, the booking will be considered a no-show, and the driver may leave.Before your ride, you’ll 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 assist with your luggage and any special requests before beginning your journey.Please note that this sightseeing ride cannot start, end, or include stops at airports, ports, or train stations.If you have any special requirements — such as traveling with a service animal or needing extra assistance — kindly mention them when booking to ensure a smooth and enjoyable experience.
What To Expect
Book Online
Safe & secure • Easy breezy • Hassle-free
Biograph Theatre
15 minutes • Admission Ticket Free
Clark Street
15 minutes • Admission Ticket Free
Holy Name Cathedral
15 minutes • Admission Ticket Free
Criminal Court Building
15 minutes • Admission Ticket Free
Harry Caray's Italian Steakhouse
30 minutes • Admission Ticket Free
business locations
30 minutes • Admission Ticket Free
Additional Info
- Confirmation is instant and will be received at time of booking
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- 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 ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
- Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance, or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative or a refund if the tickets are included in the price.
- Our tours are fully flexible — you decide which attractions to explore inside and which to admire from the outside. Entrance tickets are not included unless clearly specified as a “tickets included” option in the tour selection. Your driver will adjust the itinerary based on opening hours, availability, and your preferences to ensure a smooth and enjoyable experience.
- Operated by a business
Frequently Asked Questions
(7)Q: What is the cancellation policy for the Chicago Gangsters and Prohibition Private History Tour?
Cancellation Policy
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Activity code: C-117866P794
Reviews
Average 3.00 out of 5 stars based on 2 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from Cool Destinations customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CDT).
- Hotel pickup and drop-off.
- Fuel and Tolls.
- Water.
- WiFi on board.
- Hotel or custom pickup and drop-off.
- All taxes and handling charges.
- Professional English-speaking local driver/informal guide.
- Meals and beverages.
- Tips and Gratuities.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025There is no minimum age for this tour, so bring your wee one along for an adventure..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Chicago Gangsters and Prohibition Private History Tour is as follows:
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago Gangsters and Prohibition Private History Tour will be included in your confirmation email from Cool Destinations. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024What's Included
- Hotel pickup and drop-off
- Fuel and Tolls
- Water
- WiFi on board
- Hotel or custom pickup and drop-off
- All taxes and handling charges
- Professional English-speaking local driver/informal guide
- Meals and beverages
- Tips and Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- 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 ride, our drivers serve as informal local guides—sharing stories, history, and local tips at every stop. Please note that drivers are not permitted to enter museums or archaeological areas, but they’ll ensure you make the most of your visit with suggestions and background information before you explore on your own.
- Some stops on your itinerary may be closed on the date of travel due to public holidays, maintenance, or special events. We recommend verifying opening hours on the attraction’s official website or contacting us before your tour. If a stop is unexpectedly closed, we will try to offer a suitable alternative or a refund if the tickets are included in the price.
- Our tours are fully flexible — you decide which attractions to explore inside and which to admire from the outside. Entrance tickets are not included unless clearly specified as a “tickets included” option in the tour selection. Your driver will adjust the itinerary based on opening hours, availability, and your preferences to ensure a smooth and enjoyable experience.
- Operated by a business
