Chicago Night Crimes Tour by Bus

If you’re someone fascinated by Chicago’s colorful history—especially the crime stories that have shaped its reputation—this Chicago Night Crimes Tour by Bus offers a unique way to explore the city’s shadowy past. It’s a two-and-a-half-hour ride that takes you through the city’s most infamous crime scenes, introduces you to legendary gangsters like Al Capone, Frank Nitti, and Bugs Moran, and even lets you step off the bus to get close to history. It’s a blend of storytelling, sightseeing, and interactive fun that appeals to history buffs, crime enthusiasts, and curious travelers alike.

Two things we particularly appreciate about this tour are the expert guides—who bring the past vividly to life—and the opportunity for real photo moments at legendary crime scenes. Plus, the inclusion of a mini “mob museum” and a glimpse into Prohibition-era tunnels makes this experience more than just a sightseeing ride. On the flip side, one consideration is that the tour runs only 2 hours, slightly less than the advertised 2.5 hours, and it’s nighttime, which limits your views of Chicago’s architecture. However, if you’re ready for a lively, informative, and slightly suspenseful tour, this is a perfect fit—especially for those interested in Chicago’s crime lore and history buffs looking for something different.

This tour is best for travelers who want a mix of history, storytelling, and some fun photo opportunities in a group setting. It’s suitable for most people, but be aware that the bus isn’t equipped with an electronic lift, and there are steps and stairs involved. If you’re interested in Chicago’s underbelly without the long hikes or daytime crowds, this tour offers a compelling window into the city’s more notorious side.

Key Points

• The tour combines storytelling, sightseeing, and interactive crime scene visits.
• Guides are knowledgeable, enthusiastic, and provide detailed historical context.
• It provides great photo opportunities at famous crime sites and landmarks.
• It’s an affordable way to gain insight into Chicago’s crime-ridden past.
• The tour includes a mini mob museum and a peek into Prohibition tunnels.
• It’s ideal for anyone interested in gangster lore or Chicago’s darker history.

Exploring the Itinerary: What You’ll See and Experience

The tour starts outside 163 E. Pearson Street, conveniently located near Michigan Avenue and Pearson Street, placing you right in the heart of Chicago’s bustling downtown. From here, the bus kicks off a 2.5-hour journey into the city’s crime history, with a professional guide leading the way.

Our first stop is at the Chicago Crime Tours and Experiences headquarters, where the guide quickly sets the tone by introducing some of the city’s most infamous figures—Al Capone, John Dillinger, Frank Nitti, Dean O’Banion, and Bugs Moran. This initial segment is packed with stories that bring Chicago’s organized crime scene vividly to life. The guide’s detailed narration helps you understand how these figures influenced Chicago’s development and reputation.

One of the most compelling parts of this tour is the chance to get off the bus and explore crime scenes firsthand. At sites like the St. Valentine’s Day Massacre, you’ll stand where history played out, absorbing the gravity of that infamous event. As one reviewer noted, “The tour guide was very good & told us a lot of interesting information.” You’ll also see the handshake murder site and Nitti’s safe and tunnels, adding a tangible element to the storytelling.

Next, the bus passes by iconic landmarks such as the Museum of Contemporary Art and the John Hancock Center, giving you a sense of Chicago’s architectural grandeur. The Magnificent Mile whizzes by, offering a glimpse of the city’s upscale shopping and historic buildings, contrasting with the gritty tales you’re learning.

The Biograph Theatre is another highlight, famous for being the location where John Dillinger was shot. Though you’ll only stop for about 10 minutes, it’s an important piece of Chicago’s gangster narrative. The Jewelers Building and the historic Thirty Five E Wacker also make appearances, showcasing Chicago’s architectural history intertwined with its criminal past.

One of the most intriguing stops is at Harry Caray’s Italian Steakhouse, where you can peek inside to see Nitti’s Vault, a crime museum, and the bootlegging tunnel—a secret passageway from the Prohibition days. Guests have raved about this feature, with one saying, “Leah Nicole was amazing, warm, friendly, funny, extremely informative.” Such behind-the-scenes glimpses deepen the experience beyond simple sightseeing.

The tour continues with a walk past Holy Name Cathedral, marking the last steps of Hymie Weiss, a notorious gangster on Chicago’s North Side. As you conclude across from the Historic Water Tower, known as one of the few surviving structures from the Great Chicago Fire, you’re reminded of the city’s resilience and contrasting historical chapters.

What Makes This Tour Unique?

The tour’s emphasis on interactive elements—such as walking to crime scenes, viewing historic footage, and participating in a crime quiz—creates a lively, participatory atmosphere. The mini mob museum and the secret tunnels offer rare insights that you won’t find on typical city tours.

On top of that, the bus itself is a luxury, temperature-controlled coach that ensures comfort as you hop from site to site. The group size is limited to 39 travelers, maintaining an intimate vibe where questions are encouraged, and the guide’s enthusiasm shines through. The live commentary in English is both educational and engaging, with many reviews praising the guide’s knowledge, personality, and storytelling skills.

The Real Value of This Tour

For $55 per person, you’re getting not just a sightseeing ride but an experience filled with interesting stories, historic sites, and photo ops. The inclusion of a keepsake brochure, historic video footage, and access to a crime quiz adds layers of entertainment and education. It’s a cost-effective way to explore Chicago’s complex history, especially if you’re interested in the underworld stories that helped shape the city’s identity.

While the tour is relatively short, guests often mention that the quality of the guides and the material covered makes it well worth the price. One reviewer said, “Great guide—so much fun! Very interesting facts as well,” emphasizing the guide’s role in bringing history to life.

Practical Details: What You Need to Know

The tour departs promptly from 163 E Pearson St. It’s advisable to arrive at least 15 minutes early for check-in because guests may not join after departure. The bus is not equipped with an electronic lift, so those with mobility issues should consider this.

The tour includes no restroom breaks, so plan accordingly before boarding. No eating or drinking is permitted on the bus, making for a distraction-free ride. The tour includes photo opportunities at crime scenes, so bring your camera or smartphone.

Tip: Gratuity of around $5 per person is recommended if you enjoy the guide’s storytelling. You can pay via cash or Venmo. The tour operates rain or shine, but poor weather may result in cancellations or rescheduling.

Who Will Love This Tour?

This experience is perfect for history buffs who want a different perspective on Chicago, crime enthusiasts, and those curious about the city’s Prohibition-era stories. It’s also great for travelers who appreciate engaging guides who add personality and depth to the stories. Families with older kids interested in history and crime might find it both fun and educational.

The tour isn’t ideal if you’re seeking architectural sightseeing during daylight or if you prefer a more relaxed pace with longer stops. It’s a nighttime tour, which limits visibility of some sights but adds a mysterious, atmospheric vibe that many find exciting.

FAQ Section

How long does the tour last?
The tour runs approximately 2 hours to 2 hours 30 minutes, though some reviews suggest it might be slightly shorter. Expect a lively ride with lots of stories packed in.

Where does the tour start and end?
It begins and ends outside 163 E. Pearson Street, right across from Michigan Avenue, making it easy to access via public transportation or nearby parking.

Can I join the tour if I arrive late?
No, guests are not allowed to join after the bus departs, so arriving early is important.

Is the bus accessible for people with mobility issues?
The bus does not have an electronic lift, and there are stairs involved, so it may not be suitable for everyone with mobility challenges.

Are there any breaks during the tour?
No restroom breaks are included, so plan accordingly before boarding.

What about the weather?
The tour requires good weather and may be canceled if the weather is poor. If canceled, you’ll be offered a different date or a full refund.

Is there any food or drinks allowed?
No eating or drinking is permitted on the bus.

Can I record the tour?
Audio and video recording are not permitted without permission, respecting the guide’s instructions and intellectual property.

Final Thoughts

The Chicago Night Crimes Tour by Bus offers an engaging, accessible way to explore one of Chicago’s most intriguing facets: its notorious past. From legendary gangsters to infamous crime scenes, this tour weaves storytelling with visual stops that bring history to life. With knowledgeable guides and interactive features, it provides great value for those interested in Chicago’s underbelly.

While it’s a shorter, evening-focused experience, it’s packed with enough stories, photos, and behind-the-scenes glimpses to satisfy crime history enthusiasts and casual visitors alike. If you’re after an authentic, entertaining, and reasonably priced tour that offers a different perspective on Chicago, this ride is well worth your time.

Ideal for: curious travelers eager to learn about Chicago’s darker stories, families looking for an engaging evening activity, and anyone who appreciates lively guides and historic storytelling.

Not ideal for: mobility-challenged visitors, daytime sightseers seeking architectural tours, or guests seeking a leisurely, long-form exploration.

This tour brings Chicago’s crime-filled past vividly to life—an experience that’s both fun and educational, and a memorable way to see the city’s less-polished side.