Chicago Gangsters and Prohibition Private History Tour
Description
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.
Tour Options
Itinerary
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. Today the building remains an important landmark connected to Chicago’s criminal past. It stands as a reminder of the city’s turbulent Prohibition-era history.
St. Valentine’s Day Massacre Site. This site marks the location of the infamous St. Valentine’s Day Massacre of 1929, one of the most shocking events in American organized crime history. Seven members of a rival gang were murdered in a brutal execution widely linked to Al Capone’s criminal empire. The massacre shocked the nation and intensified efforts to crack down on organized crime. Today the site remains a powerful symbol of Chicago’s gangster era.
Holy Name Cathedral. Holy Name Cathedral is one of Chicago’s most important religious landmarks, but it also has a surprising connection to the city’s crime history. In 1926, gunmen attempted to assassinate Al Capone outside the cathedral in a dramatic drive-by shooting. Capone narrowly escaped the attack, adding another chapter to the city’s violent mob conflicts. The cathedral still stands today as both a place of worship and a historic site.
Cook County Criminal Court Building. This courthouse played a central role during Chicago’s battles against organized crime. Many mobsters, gang leaders, and criminals faced trials here as authorities worked to dismantle powerful criminal organizations. The building became a symbol of the legal fight against the city’s infamous gangster networks. Its history reflects Chicago’s long struggle to restore law and order during the Prohibition era.
Harry Caray’s Italian Steakhouse (Former Mob Hangout). Located in a historic building once associated with Chicago’s criminal underworld, this location has connections to the city’s mob history. During the Prohibition era, many restaurants and clubs secretly served alcohol and became gathering places for powerful figures. Today the building is home to one of Chicago’s well-known restaurants while still preserving its intriguing past.
Chicago Loop Prohibition-Era Locations. The Chicago Loop was once filled with hidden speakeasies where illegal alcohol was served during Prohibition. Behind ordinary storefronts, secret bars operated throughout the city, often protected by powerful crime syndicates. These underground venues became central to Chicago’s nightlife during the 1920s. Walking through the area today reveals the streets where this secret world once thrived.
Highlights
What's included
Pickup Locations & Times
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.
Traveller Ratings
Important Information
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- 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.
Reviews(3)
The driver Miguel was friendly and informative. Great review of the Chicago gangster history. He even took pictures of us to remember the experience
I can’t rate the activity itself because our guide never showed up or answered any calls. Finally did speak to the tour company and they were nice but couldn’t reach the guide either. We will see how the refund process goes.
Hi Mark, sorry to hear about what happened to the tour. Definitely, this is not what we would like you to experience with Welcome. Rest assured, we are working on this case and someone from our team will reach out to you as soon as possible. Thank you for your time and for bringing this to our attention.
Want to see your hard earned money be burned right in front of your face?? Well then, you’ve found the right experience provider for that. You”ll be told that “the driver serves as a local, English-speaking professional who can share general insights and stories—similar to a knowledgeable local—but is not a certified tour guide.” Let’s clarify: There will absolutely be no general insights and no stories being provided by your driver. Your driver will stop in front of the location - play a 30 second audio recording and move on. The “English-speaking”. Most likely English won’t be the native language of your driver, which is fine. But because of this, you run the risk that your driver won’t be able to communicate with you in a coherent manner and won’t be able to read, in a coherent manner and any scripts or prompts they have been provided, setting the driver up for failure. “Professional” yeah don’t get me started on that claim. I’m not utterly confused what I paid $230 for - and where exactly that money went , was that bad we ended it after an hour. DO NOT SIGN UP FOR THIS - AVOID AT ALL COSTS. THIS IS BORDERLINE SCAM.
Hi Joseph, we apologize for any inconvenience you've experienced with your booking in Chicago. We will make sure to help you further and to do that we would appreciate more details regarding your concerns. Please reach out to us at hello@welcomepickups.com, including your booking information and our Support Team will assist you regarding this. This will also help us investigate further and ensure a smoother experience for you in the future. Thank you for bringing this to our attention.
