Unspeakable Times
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16 Crimes That Took Chicago By Storm

Updated April 23, 2020 87.2k 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.

  • Leopold And Loeb's Perfect Crime

    Two wealthy University of Chicago students, Nathan Leopold, Jr. and Richard Loeb, kidnapped and murdered 14-year-old Bobby Franks, who was Loeb's cousin.  

    The details of the murder are disputed, but it is believed Loeb lured Franks into a car under the pretense of giving him a ride home. As Loeb drove, Leopold struck Franks with a chisel, then gagged him and pulled him into the backseat, where the boy eventually died. The men then drove to Wolf Lake in Hammond, Indiana, and disposed of the body.  

    The disturbing nature of this crime intensifies when considering the motive behind Leopold and Loeb's actions. The entire murder was predetermined months in advance as an exercise in the pair's immunity to societal boundaries, given their intellectual superiority. They even concocted a fake ransom letter as a means of camouflaging their involvement in the crime. They were convinced the plan was "perfect."  

    However, Leopold left behind a key piece of evidence near Franks' body: his glasses. After intense questioning, both men confessed to the murder. They were given life sentences plus 99 years in prison.  

    Loeb was murdered by another inmate. Leopold was paroled in 1958 and lived out the rest of his days in Puerto Rico, dying of a heart attack in 1971.

  • John Dillinger Gunned Down Outside The Biograph

    Events surrounding the death of gangster John Dillinger are contentious. It is known that one of Dillinger's girlfriends, Anna Sage, agreed to help FBI agents apprehend Dillinger. Sage told agents that she, Dillinger, and another girlfriend would be seeing a movie together on the night of July 22, 1934, and to help the officers better identify the trio, she would wear an orange dress.  

    FBI agents led by Agent Melvin Purvis gathered outside the Biograph Theatre on the evening in question and waited for Dillinger, Sage, and the other woman to emerge. It is here that details become sketchy. Some allege that Dillinger identified the surrounding men as FBI agents, ran ahead of the women and tucked his hand into his coat, indicating that he was reaching for a firearm. Others insist Dillinger merely ducked into an alleyway. In either case, the notorious criminal died in a hail of bullets.

  • Patricia Columbo's Cash Grab

    In the suburb of Elk Grove, IL, northwest of Chicago, 16-year-old Patricia Columbo began a strange sexual affair with Frank Deluca, a 39-year-old married man who ran a pharmacy. Columbo would often stay over at Deluca's house, with the full knowledge of Columbo's family.

    The affair continued for another three years before Columbo and Deluca, both estranged from their families, decided to kill Columbo's parents and her brother in order to receive her inheritance money. She and Deluca crept into her family home sometime during the wee hours of May 4, 1976, and shot her mother and father dead. Columbo then bludgeoned her brother and stabbed him more than 100 times with a pair of scissors.  

    The couple was eventually apprehended when acquaintances of Deluca told police he had solicited their services for the murder before decided to commit the crime with Columbo himself. And in a final twist of irony, it was also revealed that Columbo's family had already written her out of their will, meaning that there was never any inheritance to begin with.

  • Photo: Illinois Department of Corrections / Wikimedia Commons / Fair Use

    William Heirens, The Lipstick Murderer

    Convicted of the murder of three women in 1946, William Heirens became known as the "Lipstick Killer" after leaving a chilling message on the wall of his second victim, which he scrawled in lipstick:  

    For heavens 
    Sake catch me 
    Before I kill more 
    I cannot control myself  

    Heirens got his wish after leaving a bloody fingerprint at the same crime scene. This, combined with other eyewitness accounts, led to his arrest. At the time of his death in 2012, Heirens bore the distinction of being the longest-serving inmate in Chicago history, having spent more than 65 years in prison.