The Drake Hotel

Built in 1920, this luxurious landmark has epitomized elegance and opulence for over a century. Illustrious visitors have included Bing Crosby, Frank Sinatra, Princess Diana, and several forlorn ghosts who have made the hotel their eternal home.

The Drake Hotel, "jewel of Lake Shore Drive," opened in 1920 and has long symbolized the opulence of Chicago's Gold Coast. Built by John and Tracy Drake, its ballrooms and cocktail bars have hosted Bing Crosby, Frank Sinatra, Dean Martin, Marilyn Monroe, Queen Elizabeth II, Winston Churchill, and Princess Diana.

The hotel's oldest ghost story dates to its opening night—New Year's Eve 1920—when 2,000 of Chicago's most influential citizens gathered beneath the chandeliers for a lavish gala. According to legend, a woman in a blood-red dress attended the celebration until she discovered her fiancé dancing with another woman. Devastated, she took the elevator to the 10th floor (or the roof, accounts differ) and jumped to her death.

The "Woman in Red" has been encountered ever since, not at the spot where she landed, but at locations where her emotions ran strongest in her final hour. Guests and staff report her wandering corridors near the Gold Coast Room and Palm Court, standing on the balcony edge from which she fell. Ghost hunters believe this represents a residual haunting—the traumatic energy creating an imprint that replays like a video across decades.

Another documented tragedy occurred when socialite Adele Born Williams was shot at The Drake in a case that made front-page headlines: "WOMAN SHOT AT THE DRAKE." Returning to her eighth-floor suite with her daughter, a gray-haired woman in a black Persian lamb coat stepped from the bathroom and opened fire. Adele was struck in the head and died the next day. Police never solved the murder.

The hotel is also said to be haunted by the mourning parents of 15-year-old Bobby Franks, kidnapped and murdered in the infamous Leopold and Loeb "thrill killing" of the early 1920s. His devastated parents moved to The Drake after the trial and, some say, never truly left.

Despite investigators being unable to locate anyone who personally witnessed the Woman in Red, the legend persists as one of Chicago's most enduring ghost stories, drawing paranormal enthusiasts to this elegant landmark overlooking Lake Michigan.