Chicago’s beautiful skyline looks different from the Chicago River to the coast and from the outside looking in. Some of the city’s most notable buildings have a dark history hidden in plain sight. Sometimes these historic buildings are portals to the past, holding secrets of the city’s gangster era and true crime history. These structures, scattered throughout the city, may look ordinary, but they have played host to some of the most infamous figures and events in crime history.
Chicago is home to infamous Chicago gangster sites and true crime history amongst architectural treasures; dive deeper into the hidden stories behind the beautiful historic facades with our professional tour guide.
The Raleigh Hotel–Former Flophouse for Richard Speck
This limestone office building at 648 N. Dearborn, in the heart of Chicago’s River North neighborhood, used to be the Raleigh Hotel, which served as a one-night flophouse for notorious mass murderer Richard Speck. Speck tortured and murdered 8 nursing students from South Chicago Community Hospital on July 14, 1966. “The Raleigh” lettering remains over the front entrance doors. The canopy covers the old hotel’s name unless you get close enough to the entrance.
The Kerryman-Former McGovern Saloon where Dean O’Banion Worked as a Waiter
The Kerryman, currently a beautiful bar and restaurant at 661 N. Clark Street in Chicago, was once called McGovern Saloon. Former Chicago Gangster Dean O’Banion, a fomer choir boy at Holy Name Cathedral and one of the former leaders of the North Side gang during prohibition, once worked there as a waiter and singer. After waiting on and singing to customers, he would allegedly rob drunk customers after they left the bar.
Johnny Depp frequented the Kerryman while playing the role of notorious bank robber John Dillinger in the film “Public Enemy.”
The Original Playboy Mansion
This beautiful condo building was once the original Playboy Mansion. Hugh Hefner, the founder of Playboy, built the original Playboy Mansion at 1340 N State Parkway in 1960. Shortly afterwards, Hefner hired Bobbie Arnstein as a receptionist for Playboy Magazine, then shortly became the founder’s personal assistant. Only a shortlist of VIP’s knew what happened in the Playboy Mansion. When Arnstein became involved in drugs, law enforcement thought that by arresting Bobbie, she would tell all. Unfortunately, Bobbie Arnstein died shortly after her arrest and took her secrets to the grave.
Walgreens on North Wells
This unassuming Walgreens looked similarly in 1982 when flight attendant Paula Prince bought a bottle of Tylenol. Paula Prince, like most of the world, had no idea that there was a cyanide capsule hidden in her bottle of Tylenol. This unsolved murder case still haunts Chicago, the world, and criminologists at large. The murder of 7 people in the Chicagoland area led to the advent of safety seals. Learn more about this tale on the Chicago Crime Tour or Night Crimes Tour.
The Drake Hotel
The grandeur of this century old Chicago hotel hides its criminal past. Many gangsters were known to frequent the club at the Drake Hotel during the Roaring 20s. The hotel opened in 1920 and has a secret passageway between one of the ballrooms and the general manager’s office. The Drake Hotel’s walls hold many secrets, most of which have been told by the tenured staff through the years. Connect with the past and stay for afternoon tea at the Palm Court or a late-night drink at the Coq d’Or.
As you walk the city streets, consider the layers of depth that have formed to create our beautiful Chicago. Just like the layers of the stinking onion that Chicago is named for (“shikaakwa,” means “striped skunk” or “onion” in native Algonquin), the layers of history are quite pungent! If you pay attention, you may uncover the city’s rich history filled with tales of ambition, rivalry, and the relentless pursuit of power. Join us on a Chicago Crime Tour or Night Tour to uncover the stories of even more Chicago gangster sites!
