For much of the 20th century, Chicago served as a center for organized crime in America. From the St. Valentine's Day Massacre to the death of John Dillinger outside the Biograph Theater, gangsters and their illegal activities kept the Windy City on the front page. While charismatic criminals no longer rule the city, you can visit their former hideouts and key sites in the history of organized crime on one of Chicago's crime tours.
Although better known for ghost tours, Weird Chicago Tours offers a variety of crime-centered tours. The Devil and the White City Tour follows the path of 19th-century serial killer H.H. Holmes, as described in the book of a similar name by Erik Larson, and includes stops at sites from the World's Fair of 1893. For a more modern view of Chicago serial killers, check out the Weird Chicago Serial Killer Tour, which is so disturbing that it's limited to ages 18 and over.
The Blood, Guns, and Valentines Al Capone Tour is a classic choice, including stops at Capone's house and Southside hangouts. Public Enemies fans should book the Dillinger Crime Tour, where they will see the site of Dillinger's murder by FBI agents outside the Biograph Theater. Prices, as of 2010, are $30 for adults and $20 for children 12 and under.
Weird Chicago Tours
888-GHOSTLY
weirdchicago.com
Ride around the city in black-painted school buses driven by (fake) machine gun-toting tour guides. The two-hour long tour stops at the Biograph Theater, the site of the St. Valentine's Massacre, and other gangland sites. Untouchable Tours focuses on the golden age of Chicago crime during the 1920s and 1930s, dressing up their guides as mobsters from that era and equipping them with period slang. As of 2010, tours were $28 per person.
Untouchable Tours
773-881-1195
gangstertour.com
Begun by University of Chicago graduate Paul Durica, these walking tours of the South Side vary depending on the season and interest. Check out the Tours' Facebook page for dates and descriptions of the tours, which are updated seasonally. The Leopold and Loeb Tour, which tracks the path of the infamous murderers through their Kenwood neighborhood to the killing of Bobby Franks, is a perennial favorite. Many tours end at Backstory Cafe with snacks and relevant films. As of 2010, a donation of $5 per person was suggested.
Pocket Guide to Hell Tours
facebook.com/pages/Chicago-IL/Pocket-Guide-to-Hell-Tours/75337819907
A summertime only tour for the 21+ set, Don Carlucci's Chicago Mob Tours cover a longer period of Chicago crime, ranging from Capone and Dillinger to Sam Giancana and other members of the organized crime. The tour includes dinner and a crash course in "gangster speak." Certain tour dates are set aside for charity fundraisers. Expect stops at the site of the St. Valentine's Day Massacre, Holy Name Cathedral and several old-time speakeasies. Call for pricing.
Don Carlucci's Chicago Mob Tours
815-603-5029
chicagomobtours.com
