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All around the world, the word “gangster” is synonymous with the city of Chicago. Just ask any tourist on any given day.
Tell an outsider that you’re from Chicago and watch their eyes widen with interest. Floating through their minds are names such as Dion O’Bannion, Earl Weiss, Bugs Moran, John Dillinger and the infamous Alphonse Capone. But in a city famous for bootlegging and organized crime, how many Chicagoans can tell you how bootlegging started, or what put Al Capone in the “Guinness Book of World Records?”
“Not many,” says Craig “Southside” Alton, operator of The Untouchables Tour. “Most of the people that take this tour are tourists. There was only one Chicagoan on the bus today. Usually we don’t have any.”
The Untouchables Tour has been operating for 17 years and was conceived in a drunken stupor.
“We were sitting there one day, drunk, and we got this idea about a gangster tour. Me and Don thought it was kind of funny that, in Chicago, no one had thought to do a gangster tour,” Alton says. “We figured we liked to read, so why not read up on the history of the big guys that ran this town in the 1920s and 1930s and start up a tour.”
Alton and Don Fielding not only started the company, they take turns driving the bus around the city dressed in the full 1920s getup, complete with handguns and tie clips.
With songs such as “Mambo Italiano” playing over the loudspeakers, our tour starts when the bus rounds Superior Avenue, putting us in front of the Holy Name Cathedral, where “Hymie” Weiss was gunned down in 1926, two years after Dion O’Bannion was murdered by Capone’s gang in his nearby flower shop. Parishioners who get married at Holy Name Cathedral have their pictures taken beside the bullet holes that are lodged within the church’s frame to this day.
Amid gunshot soundtracks and jazzy tunes, “Al Dante,” in his thick Italiano accent, educates us on the gangland wars that broke out in the late 1920s between Northsiders like O’Bannion, Weiss and Moran and Southsiders such as Torrio, Colosimo and Capone.
Visiting neighborhoods that go unnoticed by the tourists’ eye, Alton and Fielding maneuver the gangster cruise, squeezing under viaducts and attracting the attention of onlookers; pointing out the alley behind the Biograph Theater on Lincoln Avenue, where Dillinger was believed to have been gunned down; the South Loop, where Colosimo ran high-class casinos and brothels; and Pilsen, where Capone operated the largest brewery of its time. The tour bus takes us from the East side to the West and from the North side to the South.
“We want to give tourists a taste of the whole Chicago, not just our great downtown area,” says Alton, who manages to squeeze a bit of Chicago’s architectural culture into a tour focusing on the city’s notorious mob history. “We want to take people into the neighborhoods where real people live.”
The Untouchables Tour brings to life the roaring ’20s, when women where referred to as “toots” and “gals,” and men were gunned down 
simply for saying the wrong thing to the right guy. The tour finishes off where it starts, in front of the 600 block of N. Clark Street. Taking with them, as a souvenir, the gals hold in their hands the carnations O’Bannion held back in 1924, and the lucky winners of the-on-bus raffle take home prizes such as an Untouchables mug, a replica of The Chicago Gangwars magazine that was popular in the 1920s and ’30s or a switchblade.
A must for Chicagoans with an interest in history, The Untouchables Tour is the city’s only tour that runs all year long, with 11 weekly excursions, seven days a week.
“I did a tour once in a blizzard,” jokes “Al Dante,” as he remembers the cold January day when less than half the bus was full. “This is what we do, and it doesn’t matter how bad the weather gets. As long as there are people that want to go, we take them.”
For information and reservations, visit www.gangstertour.com or call (800) 660-8824.