Haunted Chicago: The Scary Side of the Windy City

Time Out Chicago reviewed four Chicago ghost tours, explaining what each tour entails, how interesting the guides are, how frightening the tours are, and how long they last and cost.

Reportedly the most haunted spot in all of Chicago, Bachelor’s Grove Cemetery has featured more than 100 ghostly sightings, according to GhostReserach.org. The Web site presents a photographic tour of the graveyard, showing dilapidated chain-link fences and toppled gravestones laying atop green grass strewn with fallen leaves.

The ghosts seen at Bachelor’s Grove have taken various forms, including a “Victorian farmhouse with a white picket fence, a porch swing, and a warm light coming from within.” Other visions of ghosts near the cemetery’s pond, and faces on tombstones, have given many visitors a fright.

After a night of dancing at the now defunct O’Henry Ballroom, legend has it that Resurrection Mary got into a skirmish with her boyfriend. Distraught but determined, Mary left in search of her own ride home, but was hit by a car on Archer Avenue outside the ballroom. She was found dead later, after the driver had fled the scene, and then buried at Resurrection Cemetery. Since then, drivers in the area have reported unusual encounters with a ghostly blond women dressed in white.

Resurrection Mary was made into a movie for the Chicago Horror Film Festival. Watch the spooky trailers to prepare yourself for a visit to the scene of the crime.

Indiana native John Dillinger was a notorious gangster who roamed the Midwest with his thieving gang in the 1930s. With Dillinger leading, the group killed 10, wounded seven, robbed Chicago banks and escaped from jail three times.

In May 1934, Time Magazine discussed possible sightings of Dillinger’s ghost, including on Chicago’s North Side, where an abandoned car with bloodstained seats was suspected to be remnants of a Dillinger killing.

This unpredictable villain’s ghost is also said to haunt the Biograph Theater on Lincoln Avenue in the Lakeview neighborhood of Chicago.

The Red Lion Pub has become known as much for its crooked angles and cozy atmosphere as its ghostly occurrences. It is said that the father of John Cordwell, the bar’s original owner, haunts the bar’s staircase, making climbers feel dizzy as they pass the stained-glass window. A cowboy has also been spotted—and heard—and the scent of lavender perfume has wafted through the building, perhaps the lingering effects of a young woman who passed away there in the 1950s. 

Proceed carefully past the 2100 block of North Clark Street, where a parking lot sits wedged between a senior center and an apartment building. The vacant space was the site of the St. Valentines Day Massacre involving mobster Al Capone, and visions of a gangster dressed in a double-breasted suit have surfaced in rooms at the nearby buildings.