The Chicago Gangster Tour: An Interview with Craig “Southside” Alton

The Chicago Detours team recently enjoyed the Untouchables Tour, the original Chicago gangster tour, as a team-building outing. We interviewed Untouchable Tours’ founder to learn more about his experiences creating and leading the city’s (in)famous Chicago gangster tour.

What’s been the biggest challenge in running Untouchable Tours for nearly 30 years?

The biggest problem over the past 30 years of running the gangster tour is bad hooch. You go half-blind for weeks after only a couple bottles. At best, you get “ jake leg,” were you lose all the feeling in your leg for a month. What good are a pair of getaway sticks if you can’t run?

Also, it’s difficult keeping up with the city. [They] try to demolish any thought of gangsters in the place that is known throughout the world as Chicago Bang Bang! [ed. note: Chicago Detours recently described this phenomenon in an article about the site of the St. Valentine’s Day massacre.]

Chicago gangster tour
Our guide, Babyface Bambino, on the original Chicago Gangster Tour. Photo by Amanda Scotese.

30 years ago, when we started, we did not need The Great Mayor Daley’s blessing, but we did need an Illinois licensees plate, a city sticker, and a Chicago sight-seeing license. All not available to us.

But they don’t call me Southside for nothin’, and we gibbed and jived our way around the city and the state to get what we needed. By today’s count there are 17 gangster-style tours across America from New York to Las Vegas, Minnesota to Chicago, and we cut the mustard for all of them.

What’s the most popular stop/story on your tour?

The most surprising stories on the tour are about big Al’s first “girl friend”, the mother of his only son Albert Frances, also Al’s close relationship with Lucy and Desi– yep even Lucy!

What’s the most common question you get asked during/after the tour?

Of all the questions people ask the most common one is “where can I buy a hat like that?” We tell them jump a tin bug and go to Sid’s on Maxwell St. Tell Sid we told you to come and never pay the first price he tells ya.

Are there any stops/sights/stories on the gangster tour that ended up different than what you’d first thought they were?

Over the course of 30 years there have been many stories that have changed, as new books are published, Deidre Capone’s book Uncle Al was a big game changer as she shared many never published facts about the big guy, like his favorite spaghetti sauce: walnut, garlic and oil, which I immediately made, wow! Hint: cook the oil and crossly chopped walnuts until the oil turns white, throw in lots of garlic, salt and shut it down– man that’s good eats.

Untouchable Tour gangster tour bus
From the costumes to the bus, the Untouchable Tours’ gangster tour is a Chicago icon. Photo by southie3 via Flickr.

Have you ever had guests show up in costume?

Many guests arrive in full “fish and soup'” costumes; the dolls look like the bees knees. Probation is one of the only ways to get a man to dress up because who don’t want to be a tough guy sometime.

Why do you think the Prohibition-era gang wars have such a hold on the popular imagination?

The Prohibition era still rings with people today as it’s hard to imagine a country that is dry. Our government imposed a law that the vast majority of people did not support, so guess what, they misbehaved. Local police enforcement could not and would not enforce this federal law, it wasn’t their job– the perfect recipe for corruption. Like today’s drug trade, the contraband is small and easy to hide and worth a lot. With odds like that there will always be someone desperate enough to throw the dice.

At Untouchable tours we don’t think of these guys as “bad” just … morally misaligned. So why not grab your gang and jump on the bus for some great gangster fun and history with the Untouchables during our 30 anniversary of showing folks a good time in Chicago!

 – Southside

Our thanks to Southside and the rest of the gang (rimshot) at Untouchables Tours for hosting us and answering our questions. Now we just need them to come along on one of our tours, like the Historic Chicago Walking Bar Tour where we put our own spin on some Prohibition-era gangster stories. Perhaps we gotta make ’em an offer they can’t refuse.

– Alex Bean, Chicago Detours Content Manager and Tour Guide

Interview has been lightly edited for length and clarity.


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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