Chicago’s Original Gangster Tour by Bus

Chicago’s Original Gangster Tour by Bus: A Closer Look at the City’s Notorious Past

If you’re interested in Chicago’s fascinating, sometimes infamous, history, the Chicago’s Original Gangster Tour by Bus might just be your perfect afternoon adventure. This tour promises a lively, engaging take on the city’s Prohibition-era gangsters, with guides dressed in period attire who really embrace the colorful characters of Chicago’s criminal past. With a cozy group size and highly positive reviews, it’s one of those experiences that combines education with a good dose of entertainment.

Two things we really like about this tour are its engaging storytelling and the opportunity to see the city from a different perspective. Plus, the fact that it’s done from the comfort of a climate-controlled minibus makes it accessible regardless of weather—no need to worry about walking in the heat or rain. On the flip side, a consideration is that most of the sites visited are no longer accessible for exploring on foot, which might be a bit of a letdown if you’re hoping for more hands-on site visits.

This tour is perfect for history buffs, crime story enthusiasts, or anyone curious about Chicago’s colorful past. It’s especially suited for those who enjoy storytelling with a theatrical twist, as the guide’s costume and character-driven commentary really add to the overall experience. It’s also a good fit for older kids and adults who can appreciate the history and enjoy a touch of humor.

Key Points

• Engaging Guide: The tour features a lively, knowledgeable guide who adopts the personas of the gangsters, making history feel vivid and fun.
• Comfortable Transport: Travel around the city in a climate-controlled minibus, making it easy to sit back and enjoy the stories.
• Historical Sites: About 10 key locations, including the site where Dillinger was killed and Holy Name Cathedral, highlight Chicago’s notorious past.
• Well-Reviewed: With 100 reviews and a 5-star rating, it’s clearly a popular choice.
• Value for Money: At $48, you get nearly two hours of entertaining, story-driven history—good bang for your buck.
• Limited Site Exploration: Most sites are viewed from the bus, with no stops for walking around, which works well for some but less so for others.

An Honest Look at the Chicago Mob History Bus Tour

If you’re a fan of history, crime stories, or Chicago itself, this tour offers a unique way to learn about the city’s past. What makes it stand out is the combination of education and theatrical flair. The guides don costumes and adopt personas, which adds a layer of fun and engagement that many standard city tours lack. They bring Chicago’s gangland era to life in a way that feels lively and approachable.

The Itinerary: What You Can Expect

The tour lasts about 1 hour 45 minutes, giving you a solid chunk of time to soak in the stories and see the sights without feeling rushed. It begins at 600 N Clark St, a centrally located point that’s easy to reach via public transportation. Here’s what you’ll likely cover:

Stop 1: Dillinger’s Death Site
Many reviews mention this as a highlight—the spot where John Dillinger was taken out by law enforcement. It’s a potent piece of Chicago history, and you’ll get a quick but vivid story about his demise, which is one of the most famous gangland episodes.

Stop 2: Holy Name Cathedral
This iconic church isn’t just a beautiful Gothic structure; it’s also linked to Chicago’s gangland past through Dean O’Banion, a mob figure who was a choir boy here before his violent death. Across the street, O’Banion’s flower shop handled all the mob funerals, adding a poignant layer to this location.

Throughout the tour, your guide shares lively commentary, blending historical facts with theatrical storytelling. As one reviewer put it, the information and stories are “told in character and well done,” which makes the experience engaging and memorable. Expect to see about 10 locations, some of which are private businesses or no longer exist, limiting the possibility for exploration on foot.

The Guide and Atmosphere

Based on reviews, guides like Winnie and Maria are praised for their knowledge and sense of humor. One review highlighted a guide who dressed as a flapper, adding humor and charm. Many reviewers appreciated the fun attitude, combined with well-researched historical details, making the tour both informative and entertaining.

The Transportation: Comfort Meets Practicality

Most travelers will find the climate-controlled minibus comfortable, especially on hot, rainy, or humid days. The bus’s windows are large, offering decent views, though as one reviewer noted, a trolley might offer better sightseeing opportunities. The bus can accommodate a small group—up to 10 travelers—which keeps the experience intimate and allows for personalized interaction.

The Value Proposition

At $48 per person, this tour offers a well-rounded experience for history lovers and those looking for a fun, different way to see Chicago. Considering the length and the quality of storytelling, most agree it’s a good deal. It’s a bit more affordable than some other city attractions, and you get to learn about a colorful chapter in Chicago’s history with some added theatrical fun.

What’s Not Quite Perfect?

A recurring theme in reviews is that many of the sites visited are no longer accessible for walking around. Since the tour is primarily vehicle-based, you won’t get to step out and explore each location. If you’re expecting an interactive walking experience with lots of site visits, this might be a disappointment. Also, the specific bus sent on one day had decals that limited visibility, but that’s an occasional hiccup rather than the norm.

Who Is This Tour Best For?

This experience appeals most to adults and older teens who enjoy storytelling, history, and a bit of theatrical flair. It’s ideal if you’re interested in the colorful, sometimes dark, side of Chicago’s past but prefer to experience it comfortably from a bus. Families with older children who can appreciate historical context might also find it enjoyable, but it’s less suited for very young kids.

Final Thoughts: Is It Worth It?

If you’re after an engaging, fun way to learn about Chicago’s gangster era without the hassle of walking tours or steep prices, this bus tour hits the mark. It’s a well-reviewed, highly professional experience that manages to blend humor, history, and city sights into a compact package.

For anyone curious about Chicago’s notorious past or seeking a lighthearted yet educational city experience, this tour offers a smart choice. The guides’ knowledge and theatrical approach make the stories stick, and the small group size keeps things personal. Just keep in mind that most sites are viewed from the bus, which is perfect for a relaxed experience but might leave those craving in-depth exploration a little wanting.

FAQ

How long is the tour?
The tour lasts approximately 1 hour 45 minutes, giving you enough time to cover several sites and enjoy the stories without feeling rushed.

Where does the tour start and end?
It begins and ends at 600 N Clark St in Chicago, a convenient location close to public transportation.

What is the price?
It costs $48 per person, offering a good value considering the length, entertainment, and educational content.

Is the tour suitable for children?
While primarily aimed at older kids and adults, it’s suitable for those who appreciate history and storytelling. Most reviews mention it as a fun experience for adults and older teens.

Are there any site visits or stops?
Most of the locations are viewed from the bus. There are no scheduled stops for walking around, so be prepared for an inside-seat experience.

What kind of vehicle is used?
A climate-controlled minibus. One review noted a rare exception when a decal-covered bus limited visibility, but usually, the big windows provide decent views.

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

Is it accessible for service animals?
Yes, service animals are allowed on the tour.

In summary, the Chicago’s Original Gangster Tour by Bus is a lively, humorous, and informative way to explore the city’s past. It’s especially well-suited for those who enjoy history presented with a theatrical twist and don’t mind sitting back to view the sights from a bus. If you’re looking for a fun, fact-filled journey into Chicago’s gangster era—done with style and expert storytelling—this tour is worth considering.