Chicago Gangsters and Prohibition Private History Tour
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September 2026
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Who is going?
Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
Traveler rating
2.3/5
Based on 3 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Chicago Gangsters and Prohibition Private History Tour worth booking?
Chicago Gangsters and Prohibition Private History Tour is a 2-hour experience in Chicago, United States, from $35 per person. It scores 49 out of 100 on the Outty Ranking, which we label “Worth a Look”, based on a 2.3/5 rating across 3 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 49 / 100
- Rating
- 2.3/5 (3)
- Duration
- 2 hours
- From
- $35 per person
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 abo
What you get
About this experience
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
Included
- Hotel pickup and drop-off
- Fuel and Tolls
- Water
- On-board WiFi
- Hotel or custom pickup and drop-off
- Professional English-speaking local driver/informal guide
- All taxes and handling charges
Not included
- Meals and beverages
- Tips and Gratuities
What you'll see and do
Biograph Theatre
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.
15 minutes here
Clark Street
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.
15 minutes here
Holy Name Cathedral
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.
15 minutes here
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.
15 minutes here
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.
30 minutes here
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.
30 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 travelers per booking
- Operated by
- Welcome Pickups
Know before you go
- 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.
Photos
What travelers are saying
Outty’s summary of the themes that recur across 3 traveler reviews. Written by us, not quoted from reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
2 mentionsReviewers describe the commentary as informative rather than scripted.
Photo opportunities
1 mentionThe views and photo stops come up again and again.
Traveler reviews
3 verified traveler reviews for Chicago Gangsters and Prohibition Private History Tour. Ratings and reviews provided by Viator and Tripadvisor.
Chicago Prohibition
The driver Miguel was friendly and informative. Great review of the Chicago gangster history. He even took pictures of us to remember the experience
via Viator
Good Luck
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.
Response from the operator: 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.
via Viator
Run Away - Avoid At All Costs
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.
Response from the operator: 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.
via Viator
Good to know
- Duration
- 2 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $35 to $194
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 1
- Verdict
- Worth a Look
Why this scores 49
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Chicago Gangsters and Prohibition Private History Tour: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Chicago.
How much does Chicago Gangsters and Prohibition Private History Tour cost?
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Prices start at $35 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Chicago usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Chicago Gangsters and Prohibition Private History Tour take?
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Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Chicago is not rushed.
Is Chicago Gangsters and Prohibition Private History Tour worth it?
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It holds an Outty Ranking of 49 out of 100, which we label "Worth a Look". That score blends traveler sentiment (2.3/5 across 3 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Chicago, and how flexible the cancellation terms are.
Can I cancel or reschedule Chicago Gangsters and Prohibition Private History Tour?
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Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.
Is Chicago Gangsters and Prohibition Private History Tour suitable for kids and families?
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Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.
How far in advance should I book Chicago Gangsters and Prohibition Private History Tour?
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Around 1 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Chicago can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.
What should I bring or wear?
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Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Chicago and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.
Where does Chicago Gangsters and Prohibition Private History Tour start and how do I get there?
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The exact meeting point and directions are on your voucher once you book, and they sit in central Chicago within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.
What are the best things to do in Chicago?
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Chicago's signature experience is still the architecture boat cruise, and the difference between the docent-led originals and the party-boat imitators is the single biggest quality gap in the city. Beyond the river: gangster history walks, Art Institute access, deep-dish and hot-dog crawls, and skydeck timed entry. Outty Ranking leans on guide credentials and how consistently the promised route runs. On Outty we rank every Chicago experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Original Chicago Architecture Interiors Tour: Dazzling Interiors, Chicago Murder Mystery Tour, Chicago Favorites Ultimate Food and Walking Tour. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.
When is the best time to visit Chicago?
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May to October. Winter cruises stop running when the river ices. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.
How many days do you need in Chicago?
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Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.
Do I book through Outty or through the operator?
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Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.
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