Unspeakable Times
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16 Crimes That Took Chicago By Storm

Updated April 23, 2020 89.5k views16 items

The Windy City is known for awesome things like Chicago-style pizza, the Chicago Dog, two beloved baseball teams, Second City and other prominent comedy clubs, and the Sears Tower, the tallest (or second-tallest, depending on how you look at it) building in the US. Unfortunately, crime in Chicago is another citywide hallmark, from the bootlegging mobsters of the 1920s, to the modern gangs of the South Side, to the corrupt law enforcement agents and politicians (who are, sadly, timeless).  

But it doesn't stop there: the Chicago crimes scrapbook is also full of serial killers, cultists, opportunistic murderers, and riots. Let's take a look at 16 of the worst crimes in Chicago history.

  • Photo: Unknown / Wikimedia Commons / Public Domain

    H.H. Holmes's Murder Castle

    H.H. Holmes enjoys the distinction of being one of the country's first known serial killers. Holmes designed and commissioned his own hotel. He called it the World's Fair Hotel, and the establishment opened just in time for the World Columbian Exhibition in 1893.

    Cecil Adams of The Straight Dope writes, "It was a gaudy three-story building with shops on the first floor and a bizarre labyrinth of windowless rooms, false floors, secret passages, trapdoors, and chutes above.  Holmes changed contractors several times and shuffled the workers around frequently so that no one ever got a clear idea of the floor plan or what the building was for." 

    Holmes confessed to 27 murders, though he claimed to have murdered up to 200 people in his castle. Holmes left not long after the fair ended. He was eventually apprehended and was hanged in 1896.  

    Holmes's hotel, which became known as the "Murder Castle," burned down in 1895.

  • Saint Valentine's Day Massacre

    On Valentine's Day, 1929, seven members of an Irish gang were gunned down in a garage. The men were lined up against one wall of the garage by two individuals disguised as police officers, who, along with two others in civilian clothes, opened fire on the Irish gangsters.

    One man was found alive at the scene, but he refused to speak about the killers' identities and perished soon after. Despite a few suspects cropping up and a handful of solid leads, no arrests were ever made in connection with the massacre.

    It is widely believed that Al Capone, notorious leader of the South Side Italian Gang, orchestrated the attack.

  • Photo: Dallas Police Department / Wikimedia Commons / Fair Use

    Richard Speck Kills Eight Nurses In One Night

    On the evening of July 13, 1966, Richard Speck broke into a townhouse in the Jeffrey Manor neighborhood and held nine student nurses from the South Chicago Community Hospital hostage in one of their rooms. He murdered eight of the nurses while one hid under a bed. 

    He was ultimately arrested in 1966 after going to a hospital, a physician working there saw his "Born to Raise Hell" tattoo that was in the papers.

    Initially sentenced to death, Speck's sentence was reduced to life imprisonment after capital punishment was deemed unconstitutional in 1972. He passed due to a heart attack in 1991.  

    Years later, in 1996, a video shot in prison surfaced, which showed an aged Speck, three years before his passing, boasting about his crimes. The killer is heard saying on the tape, "If they only knew how much fun I was having in here, they would turn me loose."

  • The Killer Clown

    John Wayne Gacy assaulted and murdered 33 known young boys between 1972 and 1978, with the death count likely higher. Gacy became known as the "Killer Clown" due to his appearances at parades and other events as "Pogo the Clown," a character he invented.  

    While Gacy technically lived in Norwood Park, a small community north of Chicago, he took several of his victims from the Windy City and either stowed their bodies below his house, buried them somewhere else on his property, or dumped them in the Des Plaines River.  

    Gacy was executed by lethal injection on May 10, 1994.