Chicago Night Crimes Tour by Bus

If you’re curious about Chicago’s legendary gangster lore and want to experience the city’s shadowy history after dark, this Chicago Night Crimes Tour by Bus could be just the thing. Rated a perfect 5.0 out of 5 based on over 430 reviews, it’s a popular choice for those wanting an engaging, storytelling-style adventure that balances history, mystery, and a bit of local flavor.

What we really like about this tour is how it offers a comfortable way to see key crime scenes and landmarks without the hassle of walking around late at night. Plus, the guides are often praised for being knowledgeable, making the stories both fun and informative. On the flip side, some reviews mention it’s a bit short and, at times, the visibility of buildings at night isn’t ideal, which is worth considering if clear scenery is a priority.

This experience is perfect for true crime enthusiasts, history buffs, or anyone interested in Chicago’s notorious mobster past. It’s also a solid choice if you’re traveling with a group that enjoys storytelling and a bit of mystery—though it’s geared more toward adults and older teens, given the content.

Key Points

• Highly rated and well-loved by past participants for knowledgeable guides and interesting stories.
• Comfortable bus transportation with stops at crime scenes, allowing for exploration.
• Around 2.5 hours long, making it manageable without being overwhelming.
• Great for fans of true crime or Chicago history looking for a different perspective on the city.
• Moderate price point at $55 per person, offering good value considering the guided storytelling and access.
• Limited visibility at night might be a downside for some, but the storytelling and stops compensate well.

What to Expect on the Chicago Night Crimes Tour by Bus

This tour is designed as a fun, atmospheric exploration of Chicago’s darker history, all experienced from the comfort of a temperature-controlled coach. It kicks off around 7:30 PM at the southeast corner of N. Michigan Avenue and E. Pearson Street, a central location close to many Chicago highlights. From there, your guide—who’s often praised for being engaging and full of interesting details—begins narrating stories that bring to life the city’s notorious past.

The Route & Stops

The Tour Itself: We love the way this tour combines storytelling with actual stops at crime scenes and landmarks. You’ll visit areas associated with legendary mobsters like Al Capone, John Dillinger, Frank Nitti, and Bugs Moran. The guide walks you through their stories, explaining their ties to Chicago and highlighting some of the city’s most infamous episodes, like the St. Valentine’s Day Massacre.

Stops with Exploration: When the bus pulls over, you get the chance to step off and look around. This is where the tour really shines, as it lets you get a feel for the place and snap photos. Past guests have found these moments particularly engaging, with one reviewer noting, “The locations really brought the experience to life.”

Notable Crime Scenes & Landmarks

St. Valentine’s Day Massacre Site: Probably the most famous stop, this site is a must-see for crime history lovers. The tour’s guide recounts the bloody gang shootout and offers context about the era’s violence. It’s a sobering reminder of the city’s tumultuous past.

Biograph Theatre: You’ll pass by this historic landmark, which is closely linked to John Dillinger’s story. It adds a cinematic flavor to the tour, connecting real history with the stories you might have seen in movies.

Harry Caray’s Italian Steakhouse & Nitti’s Vault: Visiting these spots gives a taste of Chicago’s nightlife and mafia connections. Harry Caray’s is a well-known eatery, but inside, you’ll find some crime memorabilia, including Nitti’s Vault—a crime museum area showcasing Prohibition-era artifacts, tunnels, and more.

The Water Tower & Holy Name Cathedral: These landmarks, especially the Water Tower, add a touch of Chicago’s resilience—surviving the Great Fire—while also serving as a backdrop to stories of gangsters and bootlegging. Walking past Holy Name Cathedral, the guide shares tales of gang leader Hymie Weiss.

The Experience & Atmosphere

The tour is designed to be immersive, combining a lively narration with visual cues like videos and old footage. Reviewers frequently mention the guides’ enthusiasm—one said, “Kathryn was personable and well-prepared”—which really adds to the enjoyment.

However, since it’s a nighttime tour, visibility can be limited, and some travelers noted that buildings aren’t always clearly visible in the dark. One reviewer advised, “If you want better views of the city, go during the day,” but appreciated that the night ambiance added mystery.

Duration & Group Size

Clocking in at about 2 hours to 2.5 hours, this tour is a manageable way to spend an evening. The group size is limited to 39 travelers, so it tends to feel intimate enough for questions and interaction. The bus features comfortable, climate-controlled seating, making it suitable for all weather conditions—though note, the bus isn’t equipped with an electronic lift, and there are steps involved.

Price & Value

At $55, the tour offers a lot of value for anyone interested in Chicago’s crime history. Past guests have called it “worth every penny,” especially given the access to crime scenes, the knowledgeable guides, and the storytelling element. Some reviews, however, have mentioned that the tour ended earlier than expected or felt slightly rushed, so managing expectations about the duration is worth considering.

Food & Extras

The tour includes a visit to Harry Caray’s Steakhouse, which is seen as an added bonus—some guests even mentioned seeing Nitti’s Vault or exploring the bootlegging tunnels. There’s also a small mob museum and a crime quiz, adding a playful element to the night. The finale often includes a Chicago-style pizza treat, which many find a tasty way to end the evening, though some advise not to rely solely on this for your deep-dish experience.

The Real-World Experience: Pros and Cons

Pros:
– Expert guides bring stories to life and answer questions.
– Stops at crime scenes give an authentic feel and great photo opportunities.
– The overall vibe is engaging and educational—many reviews highlight how much they learned.
– The comfort of a bus means you can relax while still exploring Chicago’s dark past.

Cons:
– Limited visibility at night might mean not seeing much of the cityscape.
– The tour length can feel short for some, especially if you’re really into the details.
– No restroom breaks during the tour—plan accordingly.
– The bus isn’t wheelchair accessible, so check if this applies to you.

Who Should Consider This Tour?

If you’re fascinated by Chicago’s mobster legends and enjoy stories told with flair, this tour is a worthwhile pick. It’s especially suited to adults and older teens due to the crime-focused content, which includes violence and other mature themes. If you’re traveling with a group of true crime fans or history buffs looking for a fun, atmospheric night activity, it’s a great choice.

However, if you prefer seeing city views in daylight or want a more comprehensive tour of Chicago’s architecture and neighborhoods, you might want to consider other options. Also, if clear scenery and photography are priorities, daytime tours or walking explorations could serve you better.

Final Thoughts: Is It Worth It?

For the price of $55, this Night Crimes Tour offers a compelling glimpse into Chicago’s darker side, told by guides who clearly love what they do. The combination of storytelling, historic sites, and the chance to explore crime scenes makes it memorable. Past guests rave about how enlightening and fun it is, which is a good indicator that it hits the mark for many.

This tour is perfect for those who want an entertaining, educational experience that feels a bit like stepping into a crime novel. If you’re a fan of Chicago’s mob history or true crime in general, you’ll probably find it worthwhile. Just remember, it’s a nighttime adventure—so don’t expect to see city lights or skyline views at their best.

FAQ

Is this tour suitable for children?
This tour is primarily aimed at adults and older teens. The content includes crime stories and themes that may not be appropriate for young children.

How long does the tour last?
The tour runs approximately 2 to 2.5 hours, giving you enough time to explore crime scenes and hear stories without it feeling too long.

What is the starting point?
It begins outside 163 E. Pearson Street, at the southeast corner of Michigan Avenue and Pearson Street, a central and accessible location.

Can I join the tour late?
No, guests cannot join after the bus departs, so arriving early is recommended.

Is parking available?
The tour is near public transportation, and the meeting point is centrally located, but check local parking options ahead of time.

What should I bring?
Dress warmly for the evening, and plan ahead—no restrooms or food are available on the bus.

Are there any accessibility issues?
Yes, the bus is not equipped with an electronic lift, and there are steps involved, so it may not be suitable for everyone with mobility issues.

What’s included in the tour?
The tour includes a luxury coach bus, a professional guide, live narration, photo stops, access to videos and a crime quiz, and a small mob museum.

Can I cancel if I change my mind?
Yes, cancellations are free if made at least 24 hours in advance.

Would you recommend it?
Absolutely, especially if you’re into Chicago’s gangster past and enjoy storytelling from engaging guides. It’s a fun, different way to see some of the city’s most infamous sites.

In summary, the Chicago Night Crimes Tour by Bus offers a lively, informative look at the city’s dark history. It’s ideal for anyone curious about mobsters, crime scenes, and Prohibition-era stories. While it’s not perfect—some may wish for longer duration or better night views—it delivers a fun, memorable experience that’s worth the price for many travelers. If you’re in Chicago and want to see a different side of the city, this tour might just be the midnight adventure you’re looking for.