5 WORST Crimes in Chicago History

  1. St. Valentine’s Day Massacre: The climax of Al Capone’s grip on Chicago was February 14th, 1929, when Italian goons dressed as police officers held up 7 lieutenants of the Irish North Side Gang and unleashed the fury of shotguns and Chicago Typewriters, AKA Thompson Machine Guns. It was a public execution in the broad daylight streets of Chicago, and is forever known as one of the most iconic moments in organized crime.
  2. Leopold and Loeb: These two University of Chicago students make me proud to be a Northwestern Wildcat, when in an attempt to prove their superior intellect murdered 14-year-old Bobby Franks, in what was dubbed the Crime of the Century (this was pre-OJ). One small mistake, Leopold left his glasses behind at the scene of the crime.
  3. John Dillinger: The original public enemy #1 was the head of America’s bank robbing gang, and it was Chicago where he staked out his final days, attempting to hide his identity through failed experimental cosmetic surgery. It was his love of the ladies that turned him in, as he was betrayed by the lady in red, Ana Sage, in what led to a gunfight outside Biograph Theater, still standing in Chicago today.
  4. Tylenol Murders: This 1980s case is still unsolved, where multiple Walgreens were targeted for their Tylenol packages being swapped with cyanide capsules. While it led to many of the bottle safety practices of today, it is a case that still shocks Chicagoans. 
  5. HH Holmes: This former grave-robber turned insurance fraudster cleaned up his act in time for the 1893 Chicago World’s Fair, opening a hotel. The only problem is 27 folks are confirmed to have checked in, and never checked out! Eventually sent to the gallows, Holmes has the distinction of being America’s first serial killer.

Andre Baronov


  • The St. Valentine's Day Massacre Site
  • The famous alleyway from a legendary crime
  • The haunted Chicago theatre

And a whole lot more!