Embark on a captivating walking tour that delves into the intriguing legacy of the Midwest's most notorious mobsters and gangs. Immerse yourself in the rich history of the Windy City as you stroll through its vibrant streets, where the echoes of a century of Mob activity intertwine with the modern cityscape. Traverse the iconic Michigan Avenue, once a hub of illicit operations masterminded by the infamous Al Capone, and uncover the hidden secrets of the past that now lie beneath the surface of changing demographics and contemporary establishments. Brace yourself for chilling tales of mob hits and ongoing underworld dealings, as you unravel a dark and compelling narrative that still resonates through the streets today.
Choose your pickup location
Travel comfortably in an air-conditioned vehicle
Relax in a private transfer
Enjoy a ride with a driver all the way to Maine
What To Expect
226 S Wabash Ave
Step back in time to the roaring 1920s with our Exchequer Restaurant and Pub, formerly known as the infamous 226 Club. Enjoy delicious meals in the legitimate front restaurant while imagining the hidden speakeasy in the back, rumored to have been owned by none other than Capone himself.
12 minutes • Admission Ticket Free
17 E Monroe St
Crafted with meticulous attention to detail, the Potter Palmer Collection embodies sophistication and grace. Each item is designed to reflect the opulence and refinement of the era, capturing the essence of a bygone time.
12 minutes • Admission Ticket Free
East Madison Street
Follow the footsteps of Capone as he takes down Antonio “Tony the Scourge” Lombardo, the head of Unione Siciliana, a powerful Italian cultural institution known as “the Black Hand.” Immerse yourself in the rich history of New York and Chicago’s underworld, and uncover the secrets of this notorious event. Join us on this captivating journey and discover the hidden tales of the past.
12 minutes • Admission Ticket Free
James R. Thompson Center
Located on the very site where the hotel once stood for decades, this architectural marvel pays homage to the legacy of Governor James R. Thompson, the longest-serving governor in Illinois history. Step inside and be captivated by the grandeur of this historic landmark, which served as the heart of Illinois politics from 1977 to 1991.
12 minutes • Admission Ticket Free
North Michigan Avenue
Introducing the sensational Jake Lingle, the unsung hero behind the gripping newspaper coverage of the notorious mob in the City by the Lake. While his name may not have graced the pages of the Chicago Tribune, it was his unparalleled access to sources on both sides of the law that propelled him to stardom and ultimately put a target on his back.
12 minutes • Admission Ticket Free
Highlight
Confirmation will be received within 48 hours of booking, subject to availability
Not wheelchair accessible
Service animals allowed
Near public transportation
Most travelers can participate
This tour/activity will have a maximum of 30 travelers
Include
Well-trained guide
Excellently researched history
Exclude
Gratuities