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Untouchable Tour - Chicago's Original Gangster Tour

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Why Untouchable Tour - Chicago's Original Gangster Tour is a fun option when searching for things to do near me with friends and family

The Untouchable Tour in Chicago offers an immersive and historically accurate journey through the city's infamous gangster past during the 1920s and 1930s Prohibition Era. What makes this tour a memorable meet-up spot for friends is its unique combination of education and entertainment, delivered through engaging storytelling by professional actors who adopt the personas of 1920s gangsters. This theatrical approach brings to life the exploits of iconic figures such as Al Capone, Bugs Moran, and John Dillinger along the tour’s route. Participants ride a comfortable bus that stops at key historical locations such as the St. Valentine’s Day Massacre site, the Biograph Theatre where Dillinger was killed, and the Holy Name Cathedral, offering guests a vivid glimpse into Chicago’s notorious criminal underworld. The tour, which lasts approximately 1 hour and 45 minutes, encourages camaraderie through interactive elements including raffles and prize giveaways. With over 35 years of experience, the Untouchable Tour is known for delivering a top-notch historical narrative combined with a fun and engaging atmosphere, making it an excellent outing for groups of friends interested in history, true crime, or theatrical experiences. Meeting at a convenient downtown location between Ohio and Ontario on Clark Street, the tour is accessible and well-organized, allowing visitors to relax and enjoy a captivating glimpse into Chicago’s gangster history.

Here's what people think of Untouchable Tour - Chicago's Original Gangster Tour

As of recent, Untouchable Tour - Chicago's Original Gangster Tour holds a 4.6-star rating based on 328 reviews.

User reviews of the Untouchable Tour overwhelmingly praise its engaging presentation and educational value, reflected in a strong 4.6-star rating from over 300 reviews. Positive feedback often highlights the authenticity and entertainment provided by the professionally trained guides who perform in character as 1920s gangsters, which adds an immersive, theatrical layer to the tour. Guests appreciate the detailed storytelling about famous mobsters and historical events, finding the combination of history and drama both informative and enjoyable. The well-planned itinerary that includes iconic Chicago crime landmarks also receives commendations for making the city's gangster past tangible and memorable. Additionally, visitors enjoy the interactive aspects such as raffles and small prizes, which enhance the group experience. On the other hand, negative reviews, though fewer, sometimes mention crowded buses or minor scheduling delays, which can reduce comfort for some guests. A small number of visitors felt the tour duration was either too short or found the theatrical approach not to their taste. Nevertheless, these critiques are relatively rare and do not overshadow the overwhelmingly positive consensus. Overall, the reviews conclude that the Untouchable Tour is a compelling and fun way to explore Chicago’s darker history with friends, blending education, entertainment, and a bit of nostalgia into an unforgettable group outing experience.

Highlights from reviewers (Most Relevant)

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Eric Senne

West side Winnie was a top-notch guide. Great storytelling and pacing. Learned a ton about Al Capone’s reign and Chicago-era Prohibition as well as Chicago history in general. Laughed along the way too. Tour took just under two hours. Comfortable AC on bus. You see multiple sites but travelers don’t actually leave the bus. Really enjoyed it.

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Ashley Gomez

So entertaining and knowledgeable. Weather was a little off today due to rain but overall it was a great tour! Glad we booked with you.

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Tory Brogan

This tour is a fit for you, if you are interested in hearing more about Chicago's history as told through the lens of some of its more notorious citizens. The tour guide was funny and engaging; it is clear she loves her city and her enthusiasm was contagious. The tour took us through areas of the city in the south, north and west sides that we wouldn't have been to otherwise, which I liked. The only drawback to the tour was that it was difficult to see most of the landmarks either because of our seat location (at the back of the tour bus) or because every day Chicagoans had parked in front of the landmark itself, which obscured the view. Through much of the tour, I thought to myself that it would be great if the bus had bigger windows, so that it was easier to see the city and the sights more easily (I also understand such things cost money.) Between the Untouchable Tour and an architectural boat tour, I feel like I have a better feel for the city.

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KC Fralick

Our tour with Toni was a highlight of our trip to Chicago! I would recommend this tour to anyone who likes history, theatrics, architecture, or true crime. Driving around on the bus, hearing the stories of the old gangsters was a really great way to see other parts of the city.

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Alexandra Sperling

Marie was an enthusiastic and friendly guide. The tour is well-paced with the right amount of information. I came with some familiarity of the history but learned a lot; I think that those with little knowledge (a.k.a. my husband) would still be able to follow the clearly articulated stories. I enjoyed the glimpses into the several Chicago neighborhoods shown on the tour.

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Why Untouchable Tour - Chicago's Original Gangster Tour may become Your Favorite Meetup Place for Catching Up, Celebrating or Just Hanging Out

Why rally at Untouchable Tour - Chicago's Original Gangster Tour with your friends?

Gathering your friends or family for a memorable outing requires a destination that combines excitement, education, and unique entertainment. Untouchable Tour - Chicago’s Original Gangster Tour perfectly fits this bill by offering an immersive experience into Chicago’s thrilling gangster past. Imagine sharing laughs, surprises, and fascinating stories while cruising the city on a luxurious limo bus that feels like a time machine to the roaring 1920s and notorious crime scenes. The tour is crafted to be engaging with charismatic guides who adopt gangster personas, filling the journey with humor, historical facts, and theatrical flair that will keep your group entertained from start to finish. With a 4.6-star rating based on over 300 reviews, it’s clear that visitors consistently enjoy this experience together as a fabulous way to bond, learn, and have fun outside the usual dining or movie options. Whether you are history buffs, casual tourists, or simply friends looking for an unconventional meet-up, this tour provides a lively, comfortable, and interactive environment that encourages connection while exploring Chicago’s infamous landmarks.

What activities does Untouchable Tour offer for a group meetup?

The main activity of Untouchable Tour is a two-hour bus ride through Chicago’s historic gangster hotspots. Riding aboard a climate-controlled limousine-style bus, your group will be seated comfortably while guides bring the gangster era to life through entertaining storytelling and detailed narratives. The guides, dressed in gangster-themed costumes, perform as characters to immerse you fully into the experience, mixing serious history with corny jokes and lighthearted banter. Throughout the tour, you’ll pass by and learn about notable sites like the Biograph Theatre, Holy Name Cathedral, and locations tied to the infamous Valentine’s Day Massacre. Unlike walking tours, this bus tour allows everyone to relax and enjoy a shared social atmosphere without worrying about walking distances or weather conditions.

The tour also includes interactive elements such as raffles with prizes, which add excitement and surprise moments that spark camaraderie among your group. The guides engage the crowd with funny stories and invitations to participate in quizzes or answer trivia questions about gangster lore, making it ideal for groups seeking both entertainment and education. While the bus does not stop at locations due to the nature of the buildings (many are private, unmarked, or deliberately uncelebrated), the vivid commentary and the inside scoop from the guides fill the gaps with engaging content so that sitting still never feels dull.

Why is Untouchable Tour the perfect place for group meetups?

Untouchable Tour’s structure and style make it exceptionally well-suited for group meetups. First, the bus comfortably seats groups together, allowing friends or families to enjoy the experience as a collective rather than in isolation. The setting encourages interaction, laughs, and shared discovery, turning a simple city tour into a bonding event. Second, the narrative-driven, theatrical presentation style keeps everyone’s attention, including young adults and seasoned history enthusiasts, ensuring no one feels bored or disconnected.

Third, the tour’s timing and flexibility make planning easy for groups. The tour is approximately two hours long, making it a manageable block of time for a daytime adventure or part of a larger outing. Booking in advance is recommended (the tour often sells out), which ensures your group can coordinate plans effortlessly. Fourth, the location and pickup on Clark Street, near downtown Chicago, makes it accessible and convenient for locals and visitors alike. It also offers a refreshing change from the typical meet-up spots like restaurants, bars, or museums.

Lastly, the unique historical theme adds an "edge" to your gathering — the gangster motif feels playful and different, creating great conversation starters and photo opportunities. This interactive experience is not just about passive sightseeing; it actively involves your group in Chicago's dramatic past in a way few tours can match, leaving everyone entertained, informed, and inspired to talk about it long after the tour ends.

What makes the guides and the atmosphere on Untouchable Tour special?

The guides on Untouchable Tour are one of its strongest assets. They are not just historians reading from a script; they are performers who take on gangster personas, blending education with entertainment. Their humor, charm, and passion for Chicago’s crime history give the tour its distinct personality. Guests report that the guides’ witty commentary, historical insights, and funny storytelling keep the mood lively and engaging. Many mention that the guides' humor and ability to bring history to life helped them and their groups feel connected and entertained throughout the journey.

The atmosphere on the bus is always vibrant and festive, often compared to a moving party with a fun historical theme. There’s music, spontaneous interactions, and even a sense of camaraderie among the diverse group of riders. Whether you're a gangster history buff or new to the theme, the guides’ entertaining approach ensures the entire group, including young adults and families, feels included and amused. This creates an inviting environment that enhances the shared experience and encourages group bonding.

Can the Untouchable Tour be enjoyed by everyone in your group?

Yes, the tour caters to a broad audience, balancing informative content with entertainment that appeals across ages and interests. While the focus is on gangster history, the storytelling style and funny, theatrical presentations ensure that even those less interested in crime history stay engaged. The humorous guides include light-hearted jokes and interactive elements like raffles, which enliven the tour and keep energy high.

Families with teenagers, groups of friends, and even couples find the tour enjoyable because it combines learning with a social and festive atmosphere. The comfortable bus environment is suitable for all fitness levels, making it an excellent inclusive experience for older adults or those who prefer not to walk much. Although the tour does not involve getting off the bus, this does not detract from the overall excitement, as the historical context and behind-the-scenes stories fill the time with interesting content.

What should your group expect when preparing for the tour?

When planning your meetup, it’s important to book ahead due to the tour’s popularity and limited seating. The tour starts from a convenient location on Clark Street, easily accessible by public transit or car. The bus is climate controlled, providing comfort regardless of the season, and large windows allow good views of the passing city landmarks.

Your group should expect a lively and informative two-hour ride filled with stories, laughs, and trivia. While there is no walking included, participants can enjoy the comfort of the bus with fellow attendees. Consider bringing a camera or smartphone for photos through the windows and be ready to engage with the guides. Snacks or drinks might be limited on board, so it’s good to plan ahead for refreshments before or after the tour.

The experience is fairly casual, so comfortable but neat attire is acceptable. Since the tour highlights a darker chapter in Chicago’s history, it’s ideal for groups interested in history, crime stories, or theatrical performances. Overall, your group will enjoy a unique way to explore Chicago’s culture outside typical tourist spots.

How does Untouchable Tour compare to other Chicago tours for groups?

Compared to conventional sightseeing tours in Chicago, Untouchable Tour offers an exclusive focus on the gangster era, blending history with humor and theatrical presentation that few others replicate. Its limo bus format differs from open-top or walking tours by offering climate comfort and a stage-like setting where guides perform their roles vividly. This makes it ideal for groups seeking a social, interactive experience rather than just scanning landmarks from a distance.

Other tours may stop frequently or focus on broader city themes, but Untouchable Tour’s niche focus enables a deep dive into Chicago’s criminal past with colorful stories and lesser-known facts about mobsters and their influence on the city's history. The 4.6 rating and consistently positive reviews reflect its reputation for delivering a high-quality, fun, and educational experience that enriches group meetups.

In addition, the competitive pricing and interactive elements, such as prize raffles, add extra value to group gatherings, making it a cost-effective option for large parties who want entertainment and history combined. For anyone looking to rally a group for a unique outing in Chicago, this is a stellar choice.


In summary, Untouchable Tour - Chicago’s Original Gangster Tour offers an unforgettable and distinct group experience full of history, humor, and fun. Its interactive, theatrical approach, combined with comfortable transportation and expertly told stories, creates a perfect ambiance for friends or family meetups. Whether exploring Chicago’s infamous crime past or simply enjoying a lively communal atmosphere, this tour makes for an exceptional, captivating group adventure.

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