Chicago Gangster Tours

Apart from New York City, nowhere in America is more closely associated to the golden era of mob activity than Chicago, Illinois. While law enforcement finally brought crime bosses to justice after the short-lived Prohibition era, tourists from around the globe flock to see the famous spots where the Public Enemy Number One and the Chicago Outfit meted out violence against opponents, were exposed with betrayal, and finally met with justice.

The mystique of Chicagoland’s gang activities have long come from the big screen and television recounting gang-on-gang violence or police pursuit of criminals, in particular during the 1920’s and Prohibition era. After all, who hasn’t heard of the terrifying “Scarface” Al Capone or the bloody St. Valentine’s Day massacre? But as time has gone by, old Chicago has been overtaken by the steel and glass of modern needs. It takes a highly trained guide to spot the hidden history uncover the best stories there are to tell. These tours can help you trace the history of your favorite criminal landmarks during your visit.

Tours uncover the history of Capone’s Chicago Outfit and his rival on the North Side, Dean O’Banion. They’ll show you the exact spot where the St. Valentine’s Day Massacre went down, and expert guides will teach you about the rise and fall of criminals such as Big Jim Calosimo, Capone predecessor Johnny Torio, and Joe Accardo. You’ll also learn how law man Eliot Ness’s famed Untouchables finally brought down the biggest mob boss in American history.

But Chicago’s criminal past includes other unsavory figures not affiliated with organized crime. There’s the famed mass murderer H. H. Holmes and his hotel of horrors, parent killers Leopold and Loeb, and the precise spot where bank robber John Dillinger was gunned down after taking in a movie.

  • Bobby’s Bike Tours: The city’s seedy criminal history comes to life on the Old Chicago Gangster Electric Bike Tour, brought to you by Bobby.
  • Chicago Crime Tours: Hop on this 1.5 to 2 hour red and yellow bus tour to see historic crime scenes, gangster hangouts, and landmarks.
  • Gangsters and Ghost Tours: A trained historian takes your family on a memorable trip through both the city’s 1920’s era gangland and ghostly haunts.