Chicago Mobster Legacy Walking Tour

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.

Meeting Point

100 E Jackson Dr

100 E Jackson Dr, Chicago, IL 60603, USA

You will meet your guide outside of the South Garden of the Art Institute of Chicago. Your guide will be wearing a white Junket t-shirt. Please arrive 15 mins early.

What to expect:

Duration: 1 hour

226 S Wabash Ave

226 S Wabash Ave, Chicago, IL 60604, USA

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

17 E Monroe St

17 E Monroe St, Chicago, IL 60603, USA

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

East Madison Street

E Madison St, Chicago, IL 60602, USA

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

James R. Thompson Center

100 W Randolph St, , Chicago, 60601-3218, Illinois

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

North Michigan Avenue

N Michigan Ave, Chicago, IL, USA

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

What's included:

• Well-trained guide
• Excellently researched history