Uncover Chicago’s Gangster Past on an Interactive True Crime Tour

Step into the shadowy world of Chicago’s most infamous gangsters, from Al Capone to John Dillinger, as you visit real crime scenes, historic mob hideouts, and legendary landmarks on this thrilling guided bus tour

Cancellation: No refunds for canceled bookings.
Highlights
  • Walk in the footsteps of Al Capone, John Dillinger, and other legendary gangsters
  • Visit real crime scenes, including the Biograph Theater and the site of the St. Valentine’s Day Massacre
  • Enjoy expert storytelling, interactive crime quizzes, and historic video footage
  • Explore six historic Chicago neighborhoods on a climate-controlled bus with…
What's Included
  • 1.5 to 2-hour guided bus tour of Chicago’s crime history
  • Stops at famous mob sites and historic landmarks
  • Live tour guide with expert true crime knowledge
  • Crime quiz, historic video footage, and a souvenir pamphlet
Additional Information
  • No restrooms on the bus; please use facilities before checking in.
  • Check-in 15 minutes early—bus departs on time.
  • Dress for the weather, as some portions take place outdoors.
  • Eating and drinking are not allowed on the bus; non-alcoholic beverages may be consumed off the bus.
Location
Chicago Crime Tours and Experiences - Gangsters, Mobsters and Criminals
East Pearson Street
Cancellation Policy

No refunds or cancelations allowed. Fees may apply for rescheduling.

Customer Ratings
4.6
(8605 Ratings)
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1 star
Nancy
Jun 16, 2025
Jay was wonderful!!!!!!!!!!! I was disappointed that we paid more online than those who walked on and paid. Also wanted to share The story of Edward "Easy Eddie" O'Hare, Al Capone's bookkeeper, is one of betrayal and redemption. Initially, O'Hare was Capone's lawyer and confidante, deeply involved in the mobster's criminal empire, particularly the greyhound racing operations. However, he later became a key informant for the IRS, providing crucial evidence that helped convict Capone on tax evasion charges. This act of defiance came at a great personal cost, as O'Hare was murdered a week before Capone's release from prison. Here's a more detailed breakdown: Early Life and Business: Edward J. O'Hare, known as "Easy Eddie," was a lawyer who became involved with Al Capone through their shared interest in greyhound racing. He ran dog tracks for Capone's syndicate in Chicago, Florida, and Massachusetts, amassing considerable wealth. Turning Against Capone: In a move that surprised many, O'Hare decided to cooperate with the IRS, providing information that helped them build a case against Capone. This decision was likely motivated by a desire to protect his son, "Butch" O'Hare, and potentially secure his admission to the Naval Academy. Providing Key Evidence: O'Hare gave investigator Frank Wilson crucial information about Capone's finances, including details about the jury tampering scheme. He also helped break the code used in Capone's ledgers. Personal Sacrifice: O'Hare's cooperation with the IRS was a dangerous undertaking. He was murdered in 1939, likely by Capone's associates, just days before Capone's release from prison. Legacy: O'Hare's son, "Butch" O'Hare, became a decorated World War II fighter pilot and was honored by having Chicago's O'Hare International Airport named after him. This act of remembrance ensures that Easy Eddie's story, and his son's heroism, are not forgotten.
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Cancellation: No refunds for canceled bookings.