About this tour
A 1.5-hour walking tour through downtown Chicago's haunted past, led by a costumed guide starting at the historic Harry Caray's Italian Steakhouse. You'll explore the city's bootlegger era, secret speakeasies, underground tunnels and violent venues tied to real criminal history and reported supernatural activity. Suited to history buffs and ghost enthusiasts aged 21+, it blends Chicago's Prohibition-era crime stories with paranormal lore.
Highlights
- Costumed guide narrates Chicago's bootlegger and speakeasy underground
- Stories of Prohibition-era murders and reported hauntings throughout downtown
- Start at Harry Caray's, a landmark linked to famous Chicago criminals
- Walking route through sites of tunnels and hidden parlours
- Tours run nightly in all weather conditions
- Adults-only experience; 21+ minimum age requirement
- Moderate fitness required; expect 1.5 hours on foot
What to expect
You'll meet your costumed guide at Harry Caray's Italian Steakhouse in downtown Chicago and begin a walking tour through the city's shadier history. The guide will lead you past sites associated with Chicago's Prohibition bootleggers, secret drinking dens and venues where real violence occurred — while sharing accounts of hauntings and spectral sightings reportedly tied to these locations. The route incorporates stories of underground tunnels, hidden speakeasies and the darker side of the city's criminal past.
The tour operates nightly regardless of weather, so expect to walk in rain, cold or heat depending on when you go. You'll cover moderate ground on foot over roughly 90 minutes. Alcoholic drinks are available for purchase at various stops, but aren't included in the tour price. The experience wraps at or near the starting point.
What travellers say
- Costumed guide adds theatrical flair to the storytelling
- Strong focus on real Chicago crime history, not generic ghost tales
- Nightly availability suits flexible schedules
- Blends Prohibition history with paranormal narrative
- Downtown location accessible and walkable
- Operates in all weather; no rain postponement or shelter
- Moderate fitness and 1.5-hour walk may exclude mobility issues
- Alcohol available for purchase, but not included in price
- 21+ age restriction limits group composition
Themes summarised by our team from public information about this tour. Verify specifics on the operator's page before booking.
Good to know
This suits adult visitors keen on Chicago's true crime history, Prohibition-era stories and ghost lore—especially those who enjoy a theatrical, narrative-driven approach to local history. It's not a séance or paranormal investigation; it's a walking history tour with a supernatural angle. You must be at least 21 years old. Moderate physical fitness is required—you'll be walking for 1.5 hours on city streets with no sitting breaks. Tours run nightly in all weather, so dress for the season; there's no shelter during the walk. The tour doesn't include alcoholic drinks, though bars and speakeasy-themed stops may offer them for separate purchase. Gratuities aren't included either. Small group size isn't specified; confirm expected group size when booking.
Tour sold and operated by Viator via Viator. Descriptions on this page are original BookNow summaries written by our team — not copied from the operator. Prices and availability are confirmed at checkout.