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

By Alex Bean on December 5, 2018


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.


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


Call: 312.350.1131
E-Mail: [email protected]