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Discover Chicago's mob past on this 1 hour 45-minute guided bus tour with lively commentary, historic sites, and gangster storytelling in Chicago.

The Chicago’s Original Gangster Tour by Bus offers a compelling look into the city’s notorious mob history during the Prohibition period. Priced at $48 per person, this approximately 1 hour 45 minutes tour promises a lively exploration of Chicago’s gangster landmarks. The tour is highly recommended, with a 5.0 out of 5 rating from 100 reviews and 93% of participants endorsing it. Its popularity is evident, with bookings exceeding five times just last week.
This tour stands out for its unique blend of historical storytelling, lively guides in gangster attire, and visits to key sites like the Biograph Theater, Holy Name Cathedral, and the site of the St. Valentine’s Day Massacre. It is particularly suited for older kids and adults who enjoy engaging history presented with humor and flair. The use of a climate-controlled minibus ensures comfort throughout the experience, though it doesn’t include stops for outside exploration, which might be a consideration for some.
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This tour focuses on Chicago’s mob history during the 1920s-1930s, with an emphasis on the exploits of legendary gangsters. The minibus transports you around the city to about 10 locations, each carrying its own story. The fun, energetic commentary from guides dressed as gangsters makes the history come alive, blending education with entertainment.
The first stop is the site where John Dillinger was killed, a pivotal moment in Chicago gangster lore. The tour also includes a visit to Holy Name Cathedral, which connects to Chicago mob history through figures like Dean O’Banion. O’Banion, once a choir boy, owned a flower shop across the street that was involved in mob activities—specifically, handling flowers for mob funerals—until he was killed in his shop in 1924.
While many sites like the Biograph Theater are part of the tour route, some locations are no longer accessible or are privately owned, making it impossible to step out and explore. However, the narrative and storytelling more than make up for it, providing vivid descriptions and historical context.

The tour departs from 600 N Clark St, Chicago, IL 60654, a central location near public transportation options. The bus used for the tour is climate-controlled, ensuring comfort regardless of weather conditions. The tour ends back at the starting point, making it convenient for planning the rest of your day.
With a maximum of 10 travelers, the tour maintains an intimate atmosphere that allows for more interaction and personalized commentary. Booking in advance is recommended due to the tour’s popularity, and free cancellation is available if needed, provided you cancel at least 24 hours in advance.

The guides are praised for their knowledge, humor, and engaging storytelling. Many reviews highlight guides like Maria and Winnie for their entertaining personalities, Chicago accents, and historical expertise. They adopt gangster costumes, which add a playful yet immersive touch to the storytelling.
The inside seating ensures a comfortable, weather-proof experience, although it means there are no stops for walking or outdoor exploration. Some feedback notes that the bus’s windows are large enough for good viewing, though one review mentioned a bus with decals that slightly obstructed the view that day—highlighting the importance of verifying vehicle conditions if possible.
Reviews consistently commend the balance of fun and facts, with guides delivering stories with humor and wit. The tour also includes gangster-themed raffle activities, enhancing the overall experience. While some wish for stops at sites, most appreciate that the inside-only format allows for a rundown without the need for walking or inclement weather concerns.

The tour covers different neighborhoods across Chicago, including North, South, and West sides, providing a broad perspective on Chicago’s gangster past. It discusses gang wars, mob confrontations, and key figures like Capone, Dillinger, and Moran. The narrative includes stories of mob activities and historical context, making it both educational and engaging.

Many reviews emphasize the guides’ expertise and charisma. Guides like Winnie and Maria are noted for delivering facts with humor and Chicago flair, making each story memorable. Their costumed appearances and dynamic storytelling significantly enhance the experience, turning a simple city tour into a lively, theatrical journey.
Since the tour does not include stops for entry or walking, it is ideal for those who prefer to sit and listen. The comfort of inside seating makes it suitable during rainy or hot weather. However, some visitors express a desire for an open trolley to get a closer look at sites, though the current bus setup offers effective sightseeing from inside.
The minimum number of travelers is not specified, but the company states that if the tour is canceled due to low bookings, a full refund or alternative date is offered. The free cancellation policy provides flexibility for planning.
This tour appeals to history buffs, true crime enthusiasts, and fans of Chicago’s gangster era. It’s especially fitting for those who value entertaining storytelling combined with historical facts. The small group size makes it ideal for travelers seeking a more personalized experience. It’s also suitable for older kids and adults, given the mature content and themes.
The Chicago’s Original Gangster Tour by Bus offers a rich, entertaining look into the city’s criminal past. The combination of lively guides, detailed storytelling, and visits to notable sites provides an authentic and fun experience. The value for money is high, and the recommendation rate of 93% underscores its popularity.
While it doesn’t include outdoor stops, the inside comfort, engaging narration, and historical depth make this tour a compelling choice for those interested in Chicago’s Prohibition-era mob history. It’s perfect for adults and older kids looking for an educational yet lively exploration of Chicago’s notorious past.
“Maria was our tour guide. We boarded the bus to a flapper, dressed young Chicago woman who had an amazing sense of humor, witty, and was an excell…”
Is this tour suitable for children?
Yes, it is suitable for older kids and adults who enjoy history and storytelling.
How long does the tour last?
The tour lasts approximately 1 hour 45 minutes.
What locations will I visit?
You will see sites like the Biograph Theater, Holy Name Cathedral, and the site of Dillinger’s death.
Is the tour accessible for people with mobility issues?
Since the tour is conducted on a minibus, it may be accessible, but specific accessibility accommodations are not detailed.
Can I cancel my booking?
Yes, free cancellation is available if canceled 24 hours in advance.
Do guides wear costumes?
Yes, guides dress in gangster attire to enhance the storytelling experience.
Is the tour indoors or outdoors?
The majority of the tour is inside the climate-controlled minibus; there are no stops for outdoor exploration.
What is the price of the tour?
It costs $48 per person, offering good value considering the length and content.
How many people are in each group?
The tour is limited to a maximum of 10 travelers for a more intimate experience.
Is there a recommended age for participants?
It is suited for older kids and adults, especially those interested in Chicago’s gangster history.