The city of Chicago holds a variety of crime and ghost stories throughout history. Here we explore the notoriously known criminals of Chicago and their crimes along with a variety of hauntings in the Chicago area.

Killer Clown

John Gacy experienced an abusive childhood and struggled with determining his sexuality. Gacy sexually assaulted and took the lives of 33 boys in the Cook County area from 1972 to 1978. He was known for dressing in a clown costume with makeup on. He was later executed in 1994. A movie was created, “To Catch a Killer”, exploring Gacy’s victims and their cases.

St. Valentine’s Day Massacre

On Valentine’s Day of 1929, seven members of an Irish bootlegging operation were killed by a rivaling Italian gang, allegedly known as Al Capone’s gang. The attackers were dressed as police officers and pretended to arrest the other gang members before shooting them. No members were put on trial for this horrific crime.

Lipstick Killer

William Heirens murdered three women in 1946 and left a message written on the wall in lipstick stating, “For heavens Sake catch me Before I kill more I cannot control myself.” He left a bloody fingerprint at the crime scene which eventually led to his conviction. At the end of his life, he was the longest held prisoner in Chicago, serving over 65 years.

Resurrection Mary

Resurrection Mary is the most notoriously known ghost in the Chicago area. The story dates back to the 1930s when a woman was allegedly hit by a car on Archer Avenue. The victim was never identified, but there have been numerous reportings of drivers encountering a woman in a white dress and shoes. It is said that she returns to Resurrection Cemetery every night.

Congress Hotel

Room 441 is allegedly haunted, as multiple incidents of a dark figure kicking people awake and terrifying noises have been reported. There is also a ghost that roams the halls, of a 6-year-old boy, who was supposedly thrown from a window of the hotel during World War I. The notorious ghosts of Al Capone and Peg Leg Johnny (a homeless man who was murdered behind the hotel) have been reported as well.