Walk out of Harry Caray’s and into Chicago’s shady past: a 90-minute, costumed evening tour that traces Prohibition-era gangsters, hidden basements, and modern ghost stories along Kinzie Street and the riverfront. Practical tips—meetup, ID rules, and transit advice—help you prepare.
More ways to explore the area's outdoor wonders
The tour opens beneath the glow of brass lamps inside Harry Caray’s Italian Steakhouse, the guide dressed like a Roaring 20s character, and the city already humming with river wind that seems to nudge you toward the dark alleys. Stepping out onto Kinzie Street, you feel the city’s layered past — brick facades, elevated tracks clattering above, and the river daring you to look for signs of the city that made and broke its notorious figures.
Difficulty
moderate
Duration
1–1.5 hours
Fitness Level
Moderate: you should be comfortable standing and walking on city sidewalks for up to 90 minutes, including occasional stairs.
Wildlife
History
The tour ties to Chicago’s Prohibition era and the Chicago Outfit; figures like Frank Nitti and Al Capone shaped the city’s illicit economy and downtown power structures.
Conservation
Respect private property and businesses during stops; support local bars/restaurants and avoid littering to minimize the tour’s impact on neighborhoods.
Reserve your spot on the Chicago Haunts and Hooligans Tour today and enjoy a trusted, highly rated experience designed to help you make the most of your adventure.
Arrive early
Plan to be inside Harry Caray’s 10–15 minutes before the start to check in and find the costumed guide by the bust.
Bring valid ID
Tours beginning at 7:30pm or later require guests 21+; bring government ID if you plan to buy alcohol during stops.
Wear supportive footwear
The route is urban with curbs, stairs and uneven sidewalks — comfortable walking shoes reduce fatigue and risk of slips.
Use public transit or rideshare
Street parking is limited downtown; transit or rideshare keeps you on schedule and avoids long walks from distant lots.
Comfortable walking shoes
Support and traction for sidewalks, stairs, and occasional wet pavement.
Government-issued photo ID
Required for 21+ tours and if you plan to purchase alcoholic drinks.
Light weatherproof jacket
Chicago evenings can turn chilly or rainy; a compact jacket keeps you comfortable.
fall
Charged smartphone
Useful for navigation, photos, and contacting the tour operator if you run late.