Chicago Haunts and Hooligans Tour

The tour meets at Harry Caray's Italian Steakhouse in River North, a building that once housed Frank Nitti, Al Capone's enforcer and the man who inherited the Outfit when Capone went to prison. Grab a drink from our tavern partner, hear how Nitti ran the operation from upstairs, then follow your guide onto the Magnificent Mile for a little under a mile of walking in the footsteps of the city's most notorious crime bosses. Keep an eye on the alleys and the river. Both have reputations.

This is a haunted history of organized crime, which means the stories cover loansharking, gambling, extortion, political corruption and murder as much as they cover ghosts. You will hear about secret parlors, the underground tunnels that moved liquor and bodies, a movie theater with a deadly past and a speakeasy or two whose patrons apparently never heard about Prohibition ending. The tour wraps up in the basement of a historic building where the past is close enough to touch, and nobody will judge you for not touching it.

The tour runs about ninety minutes, Thursday through Monday, rain or shine. Earlier departures are open to all ages; tours starting after 7:30 pm are 18 and over. Drinks are optional and purchased separately, and only guests 21+ with ID may order. Because of the walking distance and the basement visit, it is not recommended for anyone with mobility restrictions. Longtime Chicagoans tend to leave as surprised as the tourists.

What's included

• 90-minute guided walking tour of the Magnificent Mile
• Costumed guide and professional storyteller
• Opening stop at Harry Caray's with an optional drink
• Visit to the basement of a historic River North building
• Just under one mile of walking
• Not included: drinks, food, gratuity