THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
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.
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.
Book with Nightly Spirits
Book directly with Nightly Spirits for the best rates and real-time scheduling.
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Operated by Nightly Spirits · Chicago, Illinois
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.
moderate.
1–1.5 hours.
Moderate: you should be comfortable standing and walking on city sidewalks for up to 90 minutes, including occasional stairs.
Meet inside Harry Caray’s Italian Steakhouse, 33 West Kinzie Street; look for the guide in Roaring 20s costume near the front bust and arrive 10–15 minutes early.
No — tours starting at 7:30pm or later are for guests 21 and older; check start times and age rules before booking.
No — alcohol is not included. You may be able to purchase your own libations at stop(s) where permitted; bring ID.
Organizers will wait about five minutes; the group remains at the start for 15–20 minutes. Call the operator number provided in your booking if you expect a longer delay.
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.
Respect private property and businesses during stops; support local bars/restaurants and avoid littering to minimize the tour’s impact on neighborhoods.
Nightly Spirits operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Nightly Spirits
Book directly with Nightly Spirits for the best rates and real-time scheduling.
Reserve Now