Chicago Crimes Night Tour

If you’re curious about Chicago’s gritty history of gangsters, mobsters, and infamous crime scenes, the Chicago Crimes Night Tour offers a compelling way to explore the city after dark. This 2.5-hour journey takes you on a comfortable, climate-controlled bus ride through neighborhoods steeped in legend and lawlessness, revealing tales that have shaped Chicago’s identity.

What we particularly love about this experience is how it balances storytelling with sightseeing—you’re not just hearing stories, but seeing key locations where history was made. Plus, the inclusion of a mini mobster museum and exclusive crime quizzes makes it a fun, immersive experience. However, as with any tour involving stairs and steps, it might not be suitable for everyone with mobility issues.

This tour is ideal for history buffs, true crime aficionados, or anyone wanting a different perspective on Chicago’s iconic skyline and neighborhoods. It’s also a fantastic choice for those who enjoy storytelling combined with scenic city views and a bit of spooky intrigue.

Key Points

• Engaging Storytelling: Knowledgeable guides, like Javier and Leah, bring Chicago’s crime history to life with humor and passion.
• Comfortable Transport: A luxury, climate-controlled bus ensures a relaxed ride between crime scenes and landmarks.
• Authentic Locations: Walk the final steps of John Dillinger, see the site of the St. Valentine’s Day Massacre, and explore the Biograph Theater.
• Educational & Interactive: Includes historic video footage, a crime quiz, and a mini mob museum with gangster artifacts.
• Beautiful City Views: You’ll enjoy scenic vistas of Chicago’s architecture, lakefront, and neighborhoods like Lincoln Park and Gold Coast.
• Excellent Value: At $55, the tour offers a mix of entertainment, education, and sightseeing that many reviewers find worth the price.

An Honest Look at the Chicago Crimes Night Tour

This tour is not your typical sightseeing experience; it’s a dive into Chicago’s shadowy past that combines history, storytelling, and scenic city views. Starting at 163 E. Pearson Street outside the Chicago Crime Tours & Experiences office, your journey begins with a brief overview of the city’s criminal legacy. The tour lasts approximately 2.5 hours, making it a manageable, engaging evening activity.

The Transportation: Comfort Meets Convenience

The use of a luxury, enclosed, climate-controlled coach bus is a clear highlight. It allows you to relax and take in the sights comfortably, regardless of weather. Being inside also means you can focus on the stories without the distraction of city traffic or noise. This is especially appreciated in Chicago’s unpredictable weather, whether it’s a chilly evening or a warm summer night.

The Route & Key Stops

The tour covers quite a bit of ground, weaving through neighborhoods known for their historic crime scenes and colorful characters. Highlights include:

• The St. Valentine’s Day Massacre site, probably the most infamous gangland killing in U.S. history. Seeing the location where this brutal event unfolded offers a tangible connection to Chicago’s Prohibition-era gang wars.
• Walking the final steps of John Dillinger, Chicago’s most notorious bank robber, giving you a unique, on-foot perspective that many reviewers have found memorable.
• Passes by architectural landmarks like the John Hancock Center and the Magnificent Mile, which provide a stunning visual backdrop amid the crime stories.
• Stops at locations like Harry Caray’s Italian Steakhouse and Holy Name Cathedral, which, while not crime scenes, add flavor to the city’s diverse history.

The tour also includes a photo stop at the Biograph Theater, the site where Dillinger was shot, and a glimpse into secret Prohibition tunnels—a detail that adds a layer of intrigue for history lovers.

The Stories & Guides

What makes this tour stand out is the expert storytelling. Guides like Javier and Leah have been praised for their enthusiastic, energetic delivery, making complex crime histories accessible and entertaining. One reviewer noted that Javier made the experience “fun and informative,” while Leah’s energy kept the group engaged throughout.

The commentary covers a wide range of figures—Al Capone, John Dillinger, H. H. Holmes, and even lesser-known characters like Terrible Tommy O’Connor and gangster Frank Nitti. The stories about these figures are enhanced by historic video footage and a crime quiz, which add an interactive element that appeals to both adults and teens.

The Mini Mob Museum & Artifacts

A highlight for many visitors is the mini mobster museum, which contains interesting artifacts such as Frank Nitti’s safe and address book. These tangible pieces of gangster history add depth and a sense of authenticity to the experience.

The Walking & Viewing Experience

The tour involves some walking on foot—walking the final steps of Dillinger and Weiss, for example—so comfortable footwear is recommended. There’s also a drive-by of the Chicago criminal courthouse, a city landmark with a chilling history.

What You’ll Gain

Beyond the crime stories, this tour offers a stunning vantage point of Chicago’s skyline and neighborhoods. You’ll see the blend of opulence and grit that defines the city, especially in areas like the Gold Coast and Streeterville. The views of Lake Michigan and the Chicago River are picturesque, providing excellent photo opportunities.

The Price & Overall Value

At $55 per person, the tour offers good value considering the mix of storytelling, sightseeing, and exclusive access to artifacts and quizzes. Reviewers consistently mention how informative guides and comfortable transport make this a worthwhile experience, especially when compared to other urban tours.

Who Will Love This Tour?

This experience is perfect for those interested in Chicago’s criminal past or fans of true crime stories. History buffs will appreciate the detailed storytelling and historical artifacts, while casual visitors will enjoy learning about Chicago’s colorful characters in an engaging, scenic setting.

It’s also suitable for families, as the tour is both educational and entertaining, though those with mobility issues should note that there are stairs and some walking involved.

Final Thoughts

The Chicago Crimes Night Tour offers a unique blend of history, storytelling, and city sightseeing, all wrapped into a two-and-a-half-hour package. The guides’ knowledge and enthusiasm help bring Chicago’s notorious past into vivid focus, while the comfortable bus and scenic routes make the experience relaxing and visually rewarding.

For anyone curious about Chicago’s gangster legends, or simply looking for a memorable evening activity that’s a little different from the usual city tour, this experience stands out as a well-rounded option. The added bonus of a mini museum and interactive quizzes ensures you’ll leave with more than just stories—you’ll carry a deeper appreciation of Chicago’s dark, captivating history.

Frequently Asked Questions

Is the tour suitable for children?
The tour is primarily designed for adults and older teenagers interested in crime history. Children can attend, but be aware that some stories and scenes are graphic or mature in nature.

What is the transportation like?
You’re transported in a luxury, enclosed, climate-controlled coach bus—ideal for relaxing between crime scene stops and enjoying the city views.

Are there any physical limitations to consider?
The bus is not equipped with an electronic lift, and the tour includes steps and stairs. If you have mobility challenges, it’s best to plan accordingly.

Can I take photos during the tour?
Photos are encouraged at the designated stops, but video recording and filming during the bus ride are not permitted.

What neighborhoods will we visit?
You’ll pass through areas including Lincoln Park, the Gold Coast, and Streeterville, with some stops and on-foot walks in historic districts.

Is the tour family-friendly?
While suitable for older children and teenagers, the mature themes and walking component may not be ideal for very young kids.

How flexible is the booking?
You can cancel up to 24 hours in advance for a full refund. Booking now also allows you to reserve your spot with the option to pay later, offering flexibility for planning your trip.

In sum, the Chicago Crimes Night Tour offers a well-balanced mix of history, entertainment, and sightseeing that appeals to a wide audience. With knowledgeable guides, scenic routes, and a small dose of Chicago’s darker side, it’s a memorable way to see the city through a different lens.