Chicago Crimes Night Tour

If you’re curious about Chicago’s darker past, this Chicago Crimes Night Tour offers a compelling glimpse into the city’s notorious criminal history. For $55 per person, you’ll spend about two hours exploring the city’s underbelly, hearing stories of gangsters, mobsters, and infamous crime scenes while riding comfortably in a climate-controlled bus. Guided by an energetic local, this tour highlights everything from the St. Valentine’s Day Massacre to the final steps of John Dillinger, giving you both a historical and atmospheric experience.

What we love about this tour is how it combines fascinating stories with stunning city views—you’ll see Chicago’s architecture and neighborhoods in a new, gritty context. Plus, the interactive elements, like the mobster mini museum with Frank Nitti’s safe and address book, add a tangible sense of Chicago’s criminal past.

A potential downside? The tour involves steps and stairs, and the bus isn’t equipped with an electronic lift, so if you have mobility concerns, that’s worth considering. Also, video recording isn’t permitted during the ride, which might disappoint some who want to capture every moment.

This experience is best suited for history buffs, crime enthusiasts, and those who enjoy a lively storytelling atmosphere. Whether you’re a seasoned Chicago visitor or a first-timer with an interest in the city’s prohibition-era lore, this tour offers a unique way to see Chicago through its most infamous stories.

Key Points

• Authentic stories about Chicago’s most notorious criminals and crime scenes.
• Comfortable transportation on a climate-controlled bus with stops for photos and walks.
• Expert local guides with engaging, lively commentary and multimedia elements.
• Exclusive access to a mobster mini museum and interactive crime quiz adds fun and educational value.
• The tour’s cost of $55 includes quite a lot of content, making it a good value for a two-hour experience.
• Suitable for those interested in history, architecture, and crime, with some walking involved.

You can check availability for your dates here:

An In-Depth Look at the Chicago Crimes Night Tour

Setting the Scene: The Heart of Chicago’s Crime History

When you choose this Chicago Crimes Night Tour, you’re stepping into an evening that blends history, architecture, and storytelling. Starting outside 163 E. Pearson Street at the southeast corner of Pearson and Michigan Ave, you’ll board a luxury, climate-controlled bus—a wise choice for comfort on a chilly or rainy Chicago evening. The bus departs promptly, and the relaxed setting allows you to settle in and prepare for a rich storytelling journey.

What sets this tour apart is its comprehensive scope—covering everything from 19th-century gangsters to modern criminal landmarks, all narrated by a knowledgeable guide. The tour’s length of about two hours makes it manageable, yet packed with enough stories and sights to satisfy your curiosity.

Exploring Chicago’s Criminal Hotspots

First stop: the site of the famous St. Valentine’s Day Massacre—a crime scene that has become synonymous with Chicago’s gangster era. Standing near this location, you’ll get a sense of the violence that defined the city’s gang wars during the Prohibition years.

Next, you’ll drive past the Biograph Theatre, where John Dillinger’s final moments unfolded. The guide will walk you through his story, sharing details about his last stand and how it marked the end of an era. Several reviews emphasize how memorable it is to walk the same path Dillinger and Hymie Weiss followed just before their deaths, offering a visceral connection to history.

Throughout the tour, you’ll see the Jeweler’s Building, Carbide and Carbon, and the historic Chicago courthouse. The latter is especially notable because it’s where notorious cases played out. You’ll also get a drive-by shot of Holy Name Cathedral and other landmarks, all serving as a backdrop to the stories.

The Best of Both Worlds: Sightseeing and Learning

While the bus keeps you comfortable and on the move, you’ll also step off at select locations for photos and brief walks. One highlight is the mini mobster museum, which includes Frank Nitti’s safe and address book—a tangible link to Chicago’s organized crime past. This small but impactful exhibit breathes life into the stories you hear and helps you visualize the criminal underworld.

The tour also includes a specialized crime quiz—an engaging way to test what you’ve learned and add a playful element to your evening. The use of historic video footage enriches the storytelling, providing a visual sense of the era and events.

More Great Tours Nearby

Guides and Atmosphere

Multiple reviews praise the knowledgeable guides who bring energy and authenticity to the experience. For example, one reviewer mentioned Leah’s energy and storytelling prowess, while others appreciated Javier’s fun and informative style. The guides’ ability to blend humor, facts, and local insights keeps the tone lively and engaging.

The group size is first-come, first-served, and seating isn’t guaranteed, so arriving early helps secure a good spot. The interactive commentary makes the experience feel like a lively conversation rather than a scripted tour, which many travelers find more memorable.

Practicalities: What You Should Know

• Cost: At $55, this tour offers solid value considering the inclusion of a museum visit, photos, and multimedia content.
• Duration: Two hours in the evening is ideal for avoiding daytime crowds and enjoying the city lights.
• Accessibility: The bus lacks an electronic lift and includes stairs, so travelers with mobility issues should plan accordingly.
• Restrictions: No food or drinks are allowed, and recording isn’t permitted, preserving the integrity of the experience.
• Meeting point: Outside 163 E. Pearson Street, with punctual departures and clear instructions.

What Travelers Are Saying

The reviews consistently highlight the guides’ expertise and the stunning city views as major pluses. One reviewer from Ireland said, “very enjoyable, learned a lot, and saw some neighborhoods,” while a visitor from Germany called the tour “excellent” with a very comfy bus. Numerous guests also appreciated the authentic stories and fun atmosphere, with some mentioning the pizza at the end as a delightful bonus.

Final Thoughts: Is This Tour Right for You?

If you’re a history lover, true crime enthusiast, or simply looking for an engaging way to explore Chicago at night, this tour hits the mark. It offers a balanced mix of storytelling, sightseeing, and interactive elements. The price is reasonable when you consider the depth of stories, museum access, and comfortable transport involved.

However, if you have mobility issues or prefer a tour that allows more walking or is entirely on foot, you might want to consider other options. Also, if you’re seeking a narrated experience with translation options, remember this tour is in English only.

In short, this Chicago Crimes Night Tour promises an entertaining, informative, and visually compelling adventure through the city’s dark side—perfect for those eager to see Chicago from a different perspective.

FAQ

Is the tour suitable for children?
While not explicitly stated, the content is based on criminal history and may be intense for very young children. Check with the provider if you have concerns about age appropriateness.

Can I join the tour if I don’t speak English?
No, the tour is conducted in English only, with live, interactive commentary. Non-English speakers might find it challenging to fully enjoy the experience.

What should I wear?
Since the tour takes place mainly at night, dress warmly, especially during colder months, and wear comfortable shoes for the walking portions.

Is the tour accessible for people with mobility challenges?
The bus is not equipped with an electronic lift and involves steps and stairs, so it may not be suitable for guests with mobility issues.

Are there any food or drink restrictions?
Yes, food and drinks are not allowed in the vehicle to keep the bus clean and the experience respectful.

What’s included in the ticket?
Your ticket covers transportation on a luxury bus, guided commentary, access to the mini museum, historic footage, a pamphlet, and the crime quiz.

To sum it up, if you’re after a unique evening in Chicago, combining history, architecture, and a touch of crime, this tour offers excellent value and plenty of memorable moments. It’s ideal for history buffs, architecture lovers, and anyone curious about the city’s famous criminals and crime scenes. Just arrive early, settle in, and enjoy the lively storytelling that brings Chicago’s legendary criminal past to life.

You can check availability for your dates here: