Haunted Evening Chicago Gangster Pub Tour

Follow in the footsteps of some of the most famous bootleggers in Chicago history on this haunted gangster pub tour. Our stories on this tour explore some of the most famous prohibition era gangster hangouts and establishments.  Tours begin at the haunted Harry Caray’s Italian Steakhouse in downtown Chicago and are 21+ only. A costumed guide will lead tour goers on a 1.5 mile walking journey exploring the creepy past of one of Chicago’s most famous bootleggers, offering glimpses into the past and revealing the stories of long-dead phantoms and specters who still call Chicago home. You'll visit several different bars, and have time to enjoy a delicious libation (at own expense) as the guide tells them about all the spooky happenings and great history of this town!

Tours begin at haunted Harry Caray’s Italian Steakhouse in downtown Chicago's historic River North area. Guests will meet their guide, who will be wearing either a Roaring 20s Flapper or Gangster costume, and check-in. Then you will be lead on a journey through alleys, basements, around buildings, and show you what it was like to be a Chicago mobster during prohibition. Our stories on this tour explore some of the most famous prohibition era gangster hangouts and establishments. We'll visit three-four different bars where guests can grab a delicious “spirit” (at own expense) and listen to tales of gangsters past and things that go bump in the night. 21+ only. The walking tour covers approximately 1-1.5 miles and ends at The Boss Bar.