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Chicago Serial Killers (The Most Evil from the Windy City)

Worst Chicago Serial Killers

The Windy City has a history of violence. It has been the home of gangsters, a hotbed for murderers and spree killers, and so much more. There have also been many serial killers from Chicago and it’s actually been home to some of the most notorious.

We have written about serial killers from Wisconsin, killers from Texas and much more here on Ways to Die. Usually, you will get one recognizable and well-known killer and a few that people barely remember. With Chicago serial killers, it’s a different story. This is a city, not a state, yet it has produced several hugely notorious serial killers over the years.

John Wayne Gacy

We have written about this killer clown before. We even told you what his last meal was. Gacy’s story was a very disturbing one, made all the more memorable by the fact that he liked to dress up as a clown and entertain kids at parties.

Gary lived in Norwood Park Township, which was in the north of Chicago, and many of his victims were from the city. He would leave the bodies of these victims in his home and he also dumped some of them in the Des Plaines River.

Here’s an interesting fact for you, you may have noticed something different about Gacy’s clown makeup. He looks much more sinister than other clowns and this is not just because we know what he was up to and what sort of person he was underneath he makeup. It’s because his makeup used sharp edges, as opposed to the rounded edges that clowns typically use. This is done to make them seem less threatening and more friendly.

It is not known whether Gacy knew this, whether he made a simple mistake or whether he intentionally sought to create an intimidating aesthetic, but it certainly makes for a chilling fact.

H. H. Holmes

Said to be America’s first serial killer, Holmes is the man behind the murder castle. He was a fraudster who killed for money and pleasure. During the Chicago World’s Fair, a major event in the city’s history, he built a hotel which was fitted with secret rooms, slides, chutes and gas chambers, allowing him to kill the guests with a flick of a switch and then send their bodies to a specially designed killing floor in the basement, where he would butcher and dispose of them.

The hotel was a three-story building that housed shops on the first floor and hotel rooms above. After Holmes was arrested and convicted, it became a tourist hotspot and was eventually pulled down. A post office and carpark now sits on the spot where the Holmes Murder Castle once was.

William Heirens

Serial Killers Chicago

Perhaps better known by the name, “The Lipstick Killer”, Heirens was convicted of killing three women in 1946, earning his nickname because he scrawled a taunting message to the police at the crime scene of his second victim.

In this message Heiress basically begged the police to catch him, claiming to be out of control and threatening to take more lives if they didn’t stop him. Thanks to a few eyewitness reports, as well as a bloody fingerprint he left at the same crime scene as the lipstick-scrawled message, Heirens was eventually stopped.

He would go on to spend more than 60 years in prison, becoming the longest serving inmate in Chicago history before eventually taking his evil legacy with him to his deathbed in 2012.

The Ripper Crew

This was a gang of murderers who killed in the name of Satan, targeting prostitutes who they claimed to butcher and then cannibalize. And it gets worse, so if you’re of a nervous disposition, then you might want to skip the next bit because it gets nasty.

The Ripper Crew are said to have indulged in necrophilia. After they hacked off their victims’ breasts they would take it in turns to rape the wound, before masturbating into it, an act so unthinkably vile it makes Jeffrey Dahmer look like a court jester.

One of the gang was executed after their arrest in 1982, the other three were given life sentences. The leader of the gang, Robin Gecht, was actually a former employee of John Wayne Gacy.

Richard Speck

Richard Speck is actually considered a spree killer as opposed to a serial killer, but either way he has gone down in history as one of the worst serial killers from Chicago and one of the evilest murderers to ever step foot in the Windy City.

In the summer of 1966, just a couple months after the Church of Satan was formed (the same Satanic church that would inspire Chicago serial killers The Ripper Crew) and at the same time that the US was launching a full-scale war in Vietnam while defending their actions on home soil, Richard Speck was breaking into the South Chicago Community hospital and preparing for a night of terror that the city wouldn’t forget in a hurry.

Speck took 8 female nurses hostage in one of the hospital’s rooms, before executing every single one of them one at a time. He took turns stabbing or strangling the first seven women, before sexually assaulting and then murdering the eighth.

He claimed to have broken into the hospital with the intention of robbing the nurses, with the bloodbath resulting from his inebriated state. Whatever the reason, Speck’s unthinkably cruelty and sadistic actions earned him a death sentence, which was then commuted to life. He would remain in prison until 1991, at which point he died of a heart attack, his life snuffed out with a rapidity that wasn’t afforded to his victims.

According to reports that surfaced after his death, Speck was not remorseful and actually boasted about his crimes while in prison. He also claimed to be having the time of his life in prison, consuming drugs that were smuggled in and performing sex acts on his fellow inmates.

Other Chicago Serial Killers

Serial Killers from Chicago

That’s pretty much it for our list of the most notorious serial killers from Chicago. If you think we have missed anyone, let us know. There are also a few more major crimes worth mentioning that took place in this city, including:

The Saint Valentine’s Day Massacre

One of the most famous gangland murders ever, this massacre took the lives of seven members of a local Irish gang. They were lined up against a wall by killers who were dressed as police officers. When the gang members were in place, they opened fire, executing all of them. Al Capone was believed to be behind it, but the perpetrators were never caught.

Nathan Leopold and Richard Loeb

These two men kidnapped and murdered a 14-year old boy by the name of Bobby Franks. The murderers were wealthy and are said to have committed the crime purely to test the limits of their legal invincibility. In the end, they didn’t have as much power as they assumed and were both given significant jail time. Loeb was murdered by another inmate while Leopold was released on parole in 1958, before dying 13 years later.