Thinking about exploring Chicago’s darker side? This Mob and Crime Bus Tour offers a fascinating peek into the city’s notorious past, focusing on legendary gangsters like Al Capone and John Dillinger. If you’re a true crime aficionado or just curious about Chicago’s shadowy history, it’s worth considering.
What we really like about this tour is how engaging the guides are — they bring the stories of Chicago’s gangland era to life with humor and insight. Plus, the stops at iconic crime scenes and landmarks make it easy to visualize the city’s tumultuous past. However, keep in mind that the experience is primarily a bus ride, so if you’re looking for a more hands-on tour or detailed walking explorations, this might not fully satisfy.
This tour works best for those interested in Chicago’s organized crime history, architecture buffs, and travelers who appreciate storytelling over physical activity. It’s a good option if you’re on a budget and want a guided overview of the city’s criminal past without committing to a full day of activity.
Key Points

- Engaging Guides: Tour guides are knowledgeable, funny, and bring stories to life with passion.
- Iconic Crime Scenes: See the site of the St. Valentine’s Day Massacre and walk Dillinger’s final steps.
- Comfortable Transport: Enjoy a climate-controlled bus with good views of the city and its landmarks.
- Interactive Elements: Includes video footage, a crime quiz, and a mini mob museum.
- Flexible Schedule: Tours run several times a day, typically lasting 1.5 hours.
- Great Value: For around $49, you get a substantial amount of historical insight and memorable photo ops.
What to Expect from the Chicago Mob and Crime Bus Tour

This is a luxury bus experience that takes you through Chicago’s neighborhoods, focusing on its organized crime history. The bus is enclosed and climate-controlled, which is a comfort in any weather, and it offers ample opportunity to see the city’s architecture and neighborhoods linked to its crime stories.
The journey starts outside 163 E. Pearson Street, just across from Water Tower Place. The guide kicks off with an overview of Chicago’s underworld, setting the stage for stories involving Al Capone, the Chicago Mob, and the infamous St. Valentine’s Day Massacre. Expect lively commentary packed with interesting facts, some humor, and the occasional storytelling flair that keeps the mood engaging.
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The Crime Scene Stops and Walks
One of the tour’s highlights is the chance to see the actual crime scenes and even walk the final steps of notorious gangsters like John Dillinger. For example, you’ll stroll the path Dillinger and Hymie Weiss took before their deaths, giving a real sense of their dramatic ends. This adds a tangible connection to history that you won’t get just from reading a book or viewing pictures.
You’ll also get to see the Biograph Theatre, famous for Dillinger’s last escape, as well as other landmarks like Harry Caray’s Italian Steakhouse and Holy Name Cathedral. These sites, while not always directly linked to crimes, are part of the city’s broader historical fabric tied to Chicago’s criminal past.
The Mini Mob Museum and Secret Tunnels
A real treat is the mini mobster museum that houses Frank Nitti’s safe and address book. You even get to check out a spy of secret Prohibition Era tunnels, which adds a layer of intrigue to the experience. These features give a tangible sense of how the mob operated behind the scenes, which many visitors find captivating.
Video Footage and Interactive Elements
Throughout the tour, you’ll view historic video footage that complements the stories told by the guide. An interactive crime quiz and a detailed pamphlet with photos help reinforce what you’re learning and give you souvenirs to remember the day.
More Great Tours NearbyOff-Bus Exploration
While most of the tour is spent on the bus, there are stops where you can get off and walk. This flexibility is appreciated; you can stand at the crime scenes, take photos, and get a feel for the neighborhoods like River North, Streeterville, Old Town, and the Mag Mile.
The Overall Experience
Expect a 1.5-hour ride filled with stories, stunning city views, and a glimpse into the criminal underworld of Chicago. The tour runs several times a day, making it easy to fit into your schedule. It’s a relaxed pace, with plenty of opportunities to ask questions and engage with the guide.
The Value for Money

At $49 per person, this tour offers a lot for the price. You get a comfortable transportation experience, entertaining and knowledgeable guides, and access to unique crime scenes and history. Plus, the included pamphlet, video footage, and mini museum are added bonuses that make it a richer experience than just a bus ride.
Many reviews praise the excellent guides, with one reviewer saying their guide was “awesome and funny,” making the experience more memorable. Others appreciated the visual storytelling and the way the tour brought history to life.
However, some travelers note that seating isn’t guaranteed and that the bus doesn’t accommodate wheelchairs with electronic lifts, so plan accordingly if mobility is a concern.
Who Should Consider This Tour?

This experience is ideal for history buffs and crime enthusiasts who enjoy storytelling and city exploration from the comfort of a bus. It’s especially suited to those interested in Chicago’s gangland era, from the Prohibition days to modern times. If you love seeing iconic sites and hearing entertaining stories, you’ll likely find this tour worthwhile.
It’s also a good pick for travelers who want an affordable, guided overview of Chicago’s criminal past without extensive walking or multiple stops. If you’re traveling with children, keep in mind that the tour is geared towards older audiences, and some stories may be intense for younger kids.
Practical Details and Tips

- The tour lasts about 1.5 hours, with departures scheduled throughout the day.
- The meeting point is outside 163 E. Pearson Street, on the south-east side of Pearson and Michigan Avenue.
- No food or drinks are allowed in the bus, and video recording isn’t permitted, so plan to enjoy the stories and sights without distractions.
- The bus does not have an electronic lift, so plan for stairs if you have mobility concerns.
- Given that the seating is first-come, first-served, arriving early ensures you get a preferred spot, often on the right side when facing forward.
- You can cancel for free up to 24 hours in advance, giving you flexibility if plans change.
FAQ

Is this tour suitable for children?
The tour mainly focuses on crime stories and may have mature themes. It’s best for older kids or teenagers interested in Chicago’s gangster history.
Are there any stops where I can get off and explore?
Yes, you can get off the bus at certain points to see crime scenes and landmarks, such as Dillinger’s walk and other historic sites.
What should I bring?
Bring your camera for photo opportunities, and dress comfortably for the weather since you’ll be both on the bus and possibly walking for a bit.
Is the tour accessible for people with mobility issues?
The bus isn’t equipped with an electronic lift, and the tour involves stairs and steps, so it may not be suitable for everyone with mobility challenges.
How long does the tour last?
It typically runs for about 1.5 hours, making it a manageable addition to your day.
Can I cancel if my plans change?
Yes, you can cancel up to 24 hours before the tour for a full refund, offering flexibility for your travel schedule.
Chicago: Mob and Crime Bus Tour
Final Thoughts

If you’re eager to learn about Chicago’s criminal past without committing to a full-day tour or walking-heavy experience, this Mob and Crime Bus Tour hits the sweet spot. It offers a perfect blend of storytelling, iconic sites, and engaging visuals all within a comfortable, accessible setting.
The knowledgeable guides elevate the experience, making history lively and fun, even if some of the stories are darker. Plus, the value for the price is clear — for just under fifty bucks, you get a well-rounded glimpse into the city’s notorious stories, complemented by some great photo opportunities and interactive elements.
This tour is especially well-suited for history lovers, true crime fans, and anyone looking for a unique way to see Chicago’s neighborhoods through a different lens. Whether you’re a solo traveler or part of a group, it’s a solid addition to your Chicago itinerary, offering insights you won’t find in typical city tours.
Enjoy the stories, soak in the city views, and keep an eye out for the hidden layers of Chicago’s past. It’s a ride you’ll likely remember long after you leave the bus.
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