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Chicago’s Gangster Tour Guides

Da Guides

The Prohibition Era comes alive as our sharply dressed gangster guides take you on a ride back to the days when Al Capone ruled the South Side of Chicago.

Hear the true stories — as only our Untouchable guides can tell ’em — of gangster legends like Dion O’Bannion, Bugs Moran, Johnny Torrio, Machine Gun Jack McGurn and John Dillinger.


Southside … Da Brewmaster

If it has sugar in it, Southside can ferment it, brew it, or distill it! Beer, wine and hooch are the earmarks of his trade. His Polish 110 proof sour cherry cordials are known throughout the Midwest.

“If you can make bread then you can brew beer, only you gotta use more water.”

Johnny Rocco

Johnny Rocco

That’s right, He’s Johnny Rocco, see?

He made his way to Chicago from New York City just like Al. Chicago suits him just fine. You want to see the town? Sure, he’ll take ya.  Wanna go for a ride? It could be arranged. Ya need to get in that exclusive joint? He’ll get’cha in. Because he is known in this town. KNOWN!

Now that he’s back from “vacation,” it’s time to get busy again, see? It’s a big town here and ya gotta know da right people. Dat’s him. He’s known and he’ll take care of ya!

Marie Genco

Marie Genco of the Genco Pura Olive Oil Company

Of all the tours, of all the gin joints in the city, you had to walk into her’s. Don’t let the glitz and the glam fool ya, Marie aint no dizzy moll with the bright lights in her eyes. In fact, if she feeds ya that line, best to check your pockets. She’s in the know, knows how to collect, and if you plan to ask her to walk Michigan ave with you, make sure to bring a brick. She’ll give ya the lowdown with a wink and a smile. Have ya splittin a side with laughter, or wrapped with a tale from Chicago’s gritty past. Just make sure ya show your appreciation, cause no one knows how to put the squeeze on like Marie Genco, of the Genco Pura Olive Oil Company. Take her meaning?”

Biggie Blue Eyes

Gangster “Biggie Blue Eyes”

Biggie comes by it naturally. A big personality, with a bigger wealth of secrets to share. Once you get him started you’ll be thankful for the comfy seats, cause you’re in for a show. Big laughs, big gasps, and bigger surprises lay in store when Biggie’s on the scene. Hard to say if the personality is bigger than those blue peepers is deep, so make sure you don’t fall in. Biggie Blue Eyes is the kind of friend you want in the city of Broad Shoulders, so don’t cross him. That would be a BIG mistake.

Winnie Westside

Winnie Westside

A lover, a scrapper, a doll about town… Don’t let that name fool ya, if you’re lookin for the hottest spots in the city, Winnie’s ya gal (‘cept the Eastside….we don’t talk about…..nevermind). From the hottest music to the coolest “lemonade” Winnie knows where to be and when to be there (and when NOT to be for that matter).

New to the city? Looking to maintain a low profile? Winnie’s got ya covered with a plan to do it all and an alibi when ya need it. After all “I ain’t never been brought up on the same charge twice


Toni Antonelli

Toni Antonelli

Toni Antonelli (not her real name) is currently on the run due to an unfortunate incident involving Dominic the Doorknob(his real name) and the last slice of tiramisu at Anto’s Bakery. For now, she’ll remain incognito until word on the street says that her status with Dominic is reduced from “I’m AFTER You” to “Fugetaboutit.”


Johnny Three Knives

Johnny Three Knives

Johnny: a Northsider and a regular Joe. The kind of guy who’s as comfortable navigating the busy streets around Wrigley as he is navigating some young dame’s heart at the bar. The kind of guy always on the spot and looking for action.

Three-Knives: a Northsider and a shadow.  The kind of guy who knows the mean streets of Chicago and where they all lead.  The kind of guy with a sharp blade for every situation, and an even sharper wit. The kind of guy who reads crowds like dime novels and knows exactly who are the suckers.

Johnny Three-Knives: A good guy to have in your corner, only don’t ask him where he got the name, unless you’re really prepared to find out…


Slippery Sloop

Slippery Sloop began his career as a mere shaver, raising funds via a spiked lemonade stand.

These days, finding him is tough. But if you’re a swell dame or he has “business” with you, he’ll find you.

He can’t recall exactly how he was dubbed, “Slippery Sloop,” only that the name arose after a night on Lake Michigan with two flappers, a circus monkey, a bag of cement and bathtub gin – served in an actual bathtub.