Last month, Travel & Leisure named the Congress Plaza Hotel the most haunted place in Illinois, which came as a shock to precisely zero Chicagoans. We’ve all heard stories about the ghost of Al Capone and the legendary Room 441, but for my money, the Congress doesn’t hold a black flame candle (that’s a Hocus Pocus reference) to the poltergeist magnet that is the Drake Hotel.

Built in 1920 by John and Tracy Drake—the same brothers who opened the Blackstone Hotel a decade earlier on the other end of Michigan Avenue—the Drake has long symbolized the opulence of Chicago’s Gold Coast. Its ballrooms and cocktail bars have been graced by the likes of Bing Crosby, Frank Sinatra, Dean Martin, Marilyn Monroe, Queen Elizabeth II, Winston Churchill, and Princess Diana. And throughout the last century, high-profile deaths and unexplained phenomena have led to a host of ghost stories. Here are the three most popular.

The Woman in Red

The Drake’s oldest ghost story dates all the way back to New Year’s Eve, 1920, when 2,000 of Chicago’s most influential people gathered beneath the chandeliers for an opening gala. John Drake was there along with the hotel’s architect, Benjamin Howard Marshall, the same guy who designed the ill-fated Iroquois Theater.

That much is history, but according to legend, a woman in a blood-red dress was also in attendance, until she discovered her fiancé dancing with another woman. Distraught, she took the elevator to either the 10th floor or the roof (accounts differ) and jumped to her death. Today, guests at the Drake have reported seeing the Woman in Red wandering the Gold Coast Room, the Palm Court, and the 10th floor.

The Grieving Parents of Bobby Franks

You remember “Leopold and Loeb,” the rich University of Chicago students who kidnapped and murdered a 15-year-old boy just to see if they could get away with it? Almost immediately after the trial was over, the victim’s family sold their Kenwood mansion and moved into the Drake. The father, Jacob M. Franks—retired president of the Rockford Watch Company and a millionaire—died of a heart attack in his suite in 1928, just four years after his son was beaten to death. The mother, Flora, also died in the hotel nine years later. Both are interred in the Franks family mausoleum, along with their son Bobby, at Rosehill Cemetery in Lincoln Square.

The Woman in Black

One of Chicago’s weirdest unsolved mysteries occurred on January 19, 1944. “WOMAN SHOT AT THE DRAKE,” screamed the front page of the Chicago Daily Tribune the next morning. Adele Born Williams, a renowned socialite and the wife of a State Department attaché, was returning to her eighth-floor suite with her daughter when “a middle-aged gray-haired woman wearing a black Persian lamb coat” stepped out of the bathroom and began shooting at them both. Adele was hit in the head, but didn’t die until the next day.

Multiple witnesses saw the “woman in black” flee the scene on the eighth floor, but police never solved the case. To make things even weirder, the gun used in the crime was found several days later, at the bottom of a stairwell that police had searched thoroughly, and a spare key to Adele’s room that had gone missing turned back up at the front desk.

Adele Born Williams and her daughter, 1944. Photo: Chicago Daily Tribune
Adam Morgan writes about culture and history for Chicago magazine. He is the editor-in-chief of the Chicago Review of Books, a book critic at the Minneapolis Star-Tribune, and his writing has appeared in The Guardian, Poets & Writers, The Denver Post, Literary Hub, Electric Literature, and elsewhere.