Chicago Mob and Gangster Segway Tour

Starting at our Millennium Park location, this tour begins on Monroe Street, which is famous for "Mrs. Conley's Patch"—birthplace of Chicago's first gangsters, Hinky-Dink and "Bathhouse" John. Cruising down Michigan Avenue's architectural landmark row, known as “the Cliff,” we witness the hangouts of Al "Scarface" Capone, Tony "Joey Batters" Accardo, Sam "Mooney Sam" Giancana, Paul "the Waiter" Rica, and John "Papa Johnny" Torrio among many others. These are the men who made up the Chicago Mafia or the Chicago Mob that we just call “The Outfit.”

Then, unlike any other Absolutely Chicago Segway glide, we leave the outdoor wonder of the Chicago Park District and head into the guts of the city, the Loop. The South Loop is now home to universities, libraries, and cultural institutions but was once the headquarters to America's greatest criminal enterprise, the Chicago Outfit. We glide through the area formerly known as "the Levee" and explore Chicago's Blackstone Hotel. Known also as the "Hotel of Presidents," the hotel also houses the Chicago Gangster Tour's favorite spot, Al Capone's barbershop! Wrapping around the loop and back into beautiful Grant Park, we stop for a picture of our award-winning skyline.

This tour is sure to thrill anybody desiring to peer into Chicago's infamous past, but let’s not forget you'll be travelling on a device from the future! We use our Segways like a time machine to transport us into a historic adventure!

It is sure to thrill anybody desiring to peer into Chicago's infamous past, but let’s not forget you'll be travelling on a device from the future! We use our Segways like a time machine to transport us into a historic adventure!

This tour is conducted as a private tour.