Chicago is wildly haunted with ghosts from the city’s past. Below are some of the interesting homes of some of the city’s early settlers, gangsters, and other restless souls.

Harpo Studios

In 1915, the Lake Michigan  steamship the Eastland sank abruptly in the Chicago River just after departure (ballast compartments had been emptied so that more passengers could be boarded). Over 800 passengers, including over 20 entire families, were killed. The corpses were brought to the 2nd Regiment Armory until they were identified and released to the families. Today, that armory is part of Harpo Studios, home of talk-show queen and media mogul Oprah Winfrey. Ghost stories from the armory rank it among the most haunted sites in America. The ghosts range from a benevolent “gray lady” to the sounds of laughing (but unseen) children.

The Biograph Theater

It was at Chicago’s Biograph Theater that John Dillinger allegedly met his end in 1934, having been set up by girlfriend Anna Sage (the famous “Lady in Red”). While many dispute that Dillinger indeed died that night, theorizing instead that the man shot by FBI agents was not John Dillinger but in fact Jimmy Lawrence, what is certainly not disputed is the fact that something otherworldly still spends its time at the Biograph. People passing by the Biograph have reported seeing a blue, hazy figure running down the alley next to the theater, falling down, and then vanishing (mirroring the movements of Dillinger/Lawrence prior to dying). People have also reported cold spots, chills, unexplained cool breezes, and feelings of anxiety. Local business owners have even noticed that people have stopped using this alley next to the Biograph Theater as a shortcut to Halstead Street.

O’Hare Airport (Flight 191)

In terms of fatalities, the deadliest single-airline accident on US soil was the May 25, 1979 accident of American Airlines Flight 191. The flight, en route from O’Hare to Los Angeles, crashed during takeoff, killing 258 passengers, 13 crew, and 2 on the ground. The cause of the accident was attributed to the left wing engine pylon, which had been possibly been damaged during an earlier engine change. Among those on board were a number of Chicago literary figures, on their way to a booksellers’ convention in LA. Not too long after the accident, ghostly tales about the site began to spring up. According to Des Plaines police officers, motorists began reporting seeing odd, bobbing white lights in the field where the aircraft had gone down. First thought to be flashlights carried by “souvenir” hunters, all police responses to the field found it silent and deserted (even those within moments of a report). Many residents of an adjacent trailer park have reported knocks and raps, odd behavior from animals, and even front doors answered to find a worried traveler who had to “make his connection” or “find his luggage.” Another long-standing report is from the terminal at O’Hare itself. According to travelers, many have reported seeing a man making a telephone call from a booth that is located close to the departure gate that was used by Flight 191. Those who have seen him say that he is quite normal-looking, with the exception of his business suit being oddly out of date. Allegedly, he will step away from the telephone booth, walks a few steps, and then vanishes into thin air.

These are a mere three of the myriad haunted spots in the Windy City. Adam Selzer, tour guide with Haunted Chicago and now with Weird Chicago Tours, even penned a book, Your Neighborhood Gives Me the Creeps, about all of the haunts the city has to offer. Being that I’ve only been to Chicago once (I was thirteen), I haven’t had the chance to explore any of these haunted places. Have you visited these places? What good ones am I missing?

Written by Anna
Anna is the Senior Consumer & Online Marketing Specialist, responsible for Llewellyn's New Worlds of Body, Mind & Spirit, the Llewellyn Journal, Llewellyn's monthly email newsletters, and more. In her free time, Anna enjoys reading an absurd number of books; doing crossword puzzles; watching ...