Chicago Night Crimes Tour by Bus

If you’re intrigued by Chicago’s infamous gangsters and the city’s gritty crime scenes, this 2.5-hour night bus tour offers a captivating peek into the prohibition era, mob violence, and historic landmarks. Priced at $55 per person, it’s a convenient way to explore famous crime sites without the hassle of walking long distances or navigating city streets after dark. The tour departs in the evening, beginning at 7:30 pm, making it a perfect choice for those who want to see a different side of Chicago after sunset.

What makes this tour particularly appealing? First, you’ll get to visit iconic locations like the site of the St. Valentine’s Day Massacre and learn about legendary figures like Al Capone, Frank Nitti, and Bugs Moran. Second, the live narration by local guides brings the city’s notorious criminal history to life, blending storytelling with historic facts in an engaging way. We also love the inclusion of crime scene photo opportunities and exclusive access to a mini mob museum, making it more than just a drive-by experience.

One consideration? While the tour offers a fascinating overview, the nighttime views can be limited—some reviews mention that seeing the buildings at night isn’t always ideal. Plus, the bus is not equipped with an electronic lift, and there are steps and stairs involved, which could be a challenge for some travelers. This tour suits history buffs, crime enthusiasts, or anyone curious about Chicago’s colorful past—especially if you prefer guided storytelling over solo sightseeing.

Key Points

• Authentic crime history: Learn about notorious mobsters and their impact on Chicago.
• Rich storytelling: Guides provide lively, detailed narration that makes history feel alive.
• Iconic crime sites: Visit the scene of the St. Valentine’s Day Massacre and other legendary locations.
• Convenient transportation: Comfortable, climate-controlled bus with opportunities to get off and explore.
• Great value: For $55, you get an engaging, approximately 2.5-hour tour that covers a lot of ground.
• Limited nighttime visibility: Some scenic views are subdued at night, which may affect photo opportunities.

A Deep Dive into the Chicago Night Crimes Tour

If you’re visiting Chicago and have an interest in true crime, mobsters, or the city’s less glamorous history, this tour hits the mark. It’s a well-organized experience that combines history, architecture, and storytelling, all wrapped into a comfortable bus ride. The tour starts and ends at the same location on N. Pearson Street, right across from the Museum of Contemporary Art, making it easy to find and convenient for evening plans.

The Itinerary and Stops

The tour kicks off at 163 E. Pearson Street, where you’ll meet your guide and hop aboard a luxury, temperature-controlled coach. As the bus begins its journey, the guide will paint vivid pictures of Chicago’s most infamous gangsters like Al Capone, John Dillinger, and Bugs Moran. You’ll pass landmarks such as the John Hancock Center, the Magnificent Mile, and Lakeshore Drive, offering a glimpse of Chicago’s vibrant city life alongside its dark crime history.

The tour’s stops are carefully chosen to give you both visual and tactile connections to historic events. One highlight is the site of the St. Valentine’s Day Massacre, in the Lincoln Park neighborhood, where you can get off the bus and see the area that witnessed one of the most infamous gangland shootouts. Another popular stop is Harry Caray’s Italian Steakhouse, which houses Nitti’s Vault—a crime museum—and the historic bootlegging tunnel. These stops allow you to step out and absorb the atmosphere—something you can’t do on a simple drive-by.

Other points of interest include the Biograph Theater, where John Dillinger was famously gunned down, and the Holy Name Cathedral, where the last steps of gangster Hymie Weiss are marked. The tour also includes a drive-by of Oz Park and the Jewelers Building, framing the city’s architectural beauty within its criminal lore.

What You’ll Experience

The narration is lively, often humorous, and packed with intriguing stories. Travelers consistently praise their guides, like Leah Nicole and Kathryn, for their knowledge, approachability, and ability to keep the group engaged. One reviewer noted, “Our guide was knowledgeable, relatable and kept the group moving along this adventurous and historical path through Chicago’s dark history.” The storytelling is a mix of history, legend, and atmosphere, making it more than just a sightseeing drive.

You’ll also get photo opportunities at crime scenes, which is a real plus for those wanting to document their experience. Plus, the crime quiz, videos, and mini museum add layers to the tour, turning it into an educational, interactive experience.

What the Tour Includes and Excludes

For $55, you’re getting a professional guide and chauffeur, live narration in English, and access to exclusive crime history content. The tour includes storage for a folding wheelchair or stroller, which is helpful for travelers with mobility needs. You also get a keepsake brochure and a chance to see historic footage.

However, tips are not included—a recommended $5 per person is customary—and restroom breaks are not available on the bus, so plan accordingly before boarding. The bus departs exactly at 7:30 pm, so arriving 15 minutes early ensures you’re comfortably settled. Keep in mind that the bus is not wheelchair accessible, and no eating or drinking on board is allowed.

What Travelers Are Saying

The reviews are overwhelmingly positive, with a 5.0 rating from 432 reviews. Many praise the knowledgeable guides, entertaining storytelling, and well-chosen stops. One reviewer called it a “great way to spend an evening in Chicago,” especially for mobster enthusiasts. Several reviews highlight the authenticity and depth of historical detail, with comments like “The history is magnificent!” and “Our guide was fantastic!”

A few reviews note the tour ending early or the limited visibility at night. For example, one person said, “It ended 45 minutes early,” but most found the pacing suitable. Others mention that seeing buildings clearly might be better during the day, but for those interested in crime scenes, legend, and urban legends, the night ride offers a different, atmospheric perspective.

Who Will Love This Tour?

This experience will appeal most to history buffs, true crime fans, and architecture enthusiasts looking for a fun, informative evening. It’s ideal if you enjoy guided storytelling and want to see Chicago’s crime-related landmarks firsthand. If you’re traveling with someone who prefers active wandering or daylight sightseeing, this tour might feel a bit confined, but for those who love stories of gangsters and the Prohibition era, it will be a highlight.

The Sum Up

The Chicago Night Crimes Tour offers a unique blend of history, storytelling, and city sights that makes it a strong choice for visitors eager to understand Chicago’s infamous past. For just over $50, you get a comfortable, guided experience that’s both educational and entertaining. The stops at legendary crime scenes and the insider stories told by passionate guides make this tour stand out. It’s especially great for mobster enthusiasts, history lovers, or anyone interested in Chicago’s colorful, sometimes dark, past.

While the limited lighting at night might reduce some scenic views, the richness of the stories and the exclusive access to crime sites more than make up for it. The tour’s positive reviews underscore its value, with many saying it’s a must-do activity when exploring Chicago after hours.

If you’re looking for a lighthearted, yet informative adventure that dives into the city’s criminal lore, this tour is well worth considering. Just remember to arrive early, bring your curiosity, and prepare for an evening of Chicago’s shadowy stories that will stay with you long after you leave.

FAQ

How long is the Chicago Night Crimes Tour?
It lasts approximately 2 hours to 2.5 hours, starting at 7:30 pm and ending at the original meeting point.

Where does the tour start and end?
The tour begins and concludes outside 163 E. Pearson Street, on the southeast corner of N. Michigan Avenue and E. Pearson Street.

Can I join the tour late?
No, guests may not join after the bus departs, so be sure to arrive at least 15 minutes early.

Is this tour suitable for people with mobility issues?
The bus is not equipped with an electronic lift, and there are steps involved, so travelers with mobility challenges should consider this.

Are there restrooms on the bus?
No, there are no restroom breaks during the tour, so plan accordingly before boarding.

Is there a dress code?
There’s no specific dress code, but dress comfortably for an evening bus tour.

Are food and drinks allowed on the bus?
No, eating or drinking on board is not permitted.

What is included in the ticket price?
Your ticket covers transportation, guided narration, photo stops, access to exclusive content, and a keepsake brochure.

Can I cancel my booking?
Yes, full refunds are available if you cancel at least 24 hours in advance.

Is the tour family-friendly?
Most travelers find it suitable for adults and older teens, but it is focused on crime history, which may not be appropriate for very young children.

This Chicago Night Crimes Tour combines entertainment and education in a way that appeals to those eager to see the city’s dark side. It’s a value-packed experience that balances storytelling, historic sites, and city views—perfect for an evening in the Windy City.