Chicago Private Haunts and Hooligans Tour

The Private Haunts and Hooligans Tour starts at Harry Caray's Italian Steakhouse in River North, once home to Frank Nitti, Capone's enforcer and successor. Your group can order drinks while the guide sets the scene with the Outfit's rise, then you head onto the Magnificent Mile for about a mile of walking in the footsteps of the city's crime bosses. Along the way the guide points out what might be lurking in the alleyways and what the Chicago River has been known to give back, and the stories mix ghostly encounters with the loansharking, gambling, corruption and murder that built the 1920s underworld.

This is a favorite for corporate outings and team-building, because gangster history is the rare topic that works for the sales team and the engineers alike. It also suits bachelor parties, birthdays, visiting relatives and holiday parties that want something more memorable than a conference room. Private tours run every day of the week with start times from 1 pm to 9 pm, and the duration, meeting location and drink stop can all be adjusted. If your hotel is close to the route, the guide may be able to meet you there.

Pricing starts at $325 for up to 10 guests, with additional tickets from $27, and rises to $375 from mid-September through mid-November. One guide handles 15 to 20 guests depending on the date; groups of 16 or more should email to book and larger groups are split across guides. There are no food stops on the route, so eating at Harry Caray's beforehand is a solid plan. The SP+ and Greenway garages are the closest parking.

What's included

• 90-minute private gangster ghost tour, your group only
• Costumed guide and professional storyteller
• Opening stop at Harry Caray's with optional drinks
• About one mile along the Magnificent Mile
• Flexible start time, 1 pm to 9 pm, any day
• Not included: drinks, food, taxes, fees and gratuity