Haunted Chicago Walking Tour: Crime, Ghosts & Prohibition-Era Secrets
Walk the sidewalks where Al Capone and John Dillinger once walked. This 90-minute Haunted Chicago tour blends true-crime history, access to historic interiors, and local ghost stories to bring the city’s Prohibition-era underworld to life.
The Experience
Before You Go
Bring ID for building entry
Some interior stops are in hotel lobbies and bars—carry government ID in case it’s requested for access.
Wear sturdy shoes
Expect 1.0 mile on city sidewalks and a few short staircases; comfortable closed-toe shoes make the route easier at night.
Mind the light and traffic
Portions run after dark along busy streets—use a small flashlight and stay on sidewalks when crossing between stops.
Charge your phone
Mobile tickets and photos are common; keep your battery topped up or bring a power pack.
Local Knowledge
Hidden Gems
- •The Rookery Building lobby and Frank Lloyd Wright-designed stairwell
- •Pedway art installations near Washington and the smaller theater marquees off the main strip
Wildlife
- •Peregrine falcons nesting on downtown ledges
- •Urban raccoons and pigeons common near riverfront areas
Conservation Note
Tours operate with respect for historic interiors—stay on designated paths and avoid touching architectural features; small groups minimize wear on older spaces.
Chicago’s Prohibition-era violence and political corruption shaped its downtown architecture and municipal institutions; many conflicts played out in the same buildings the tour visits.
Photographer's Notes
- • Along the Chicago River bridges looking up at office façades
- • Plaza around the Picasso sculpture for scale shots
- • Chicago Theatre marquee for neon-lit portraits
What to Bring
Comfortable walking shoesEssential
Support and traction help on uneven city sidewalks and occasional stairs.
Layered jacketEssential
Chicago nights cool quickly; layering lets you adjust between heated interiors and cold streets.
Valid photo IDEssential
Required for entry to certain historic hotel lobbies and bars included on the route.
Compact flashlight or phone light
Illuminates uneven surfaces and helps with night photography.
Common Questions
How long is the tour and how far do we walk?
The tour lasts about 90 minutes and covers roughly 1.0 mile on city sidewalks with several stops.
Is the tour suitable for children or strollers?
Yes—infants and small children can ride in a stroller, but content includes true-crime history that may not be suitable for very young kids.
Are the buildings we visit actually open to the public?
Yes. The tour includes access to several historic interiors and hotel lobbies; your guide will escort the group inside where admission is included.
Is the tour wheelchair accessible?
The tour is listed as wheelchair accessible, though some older interiors may have limited access—contact the operator with specific accessibility needs before booking.
What should I bring to the tour?
Bring a valid ID, comfortable shoes, a jacket for night weather, and your mobile ticket. A small flashlight and a charged phone are also helpful.
What is the cancellation policy?
You can cancel for a full refund up to 24 hours before the scheduled departure time; after that refunds are not available.
Book This Experience
Check AvailabilityDuration
1.5 hours (90 minutes)
Location
Chicago, Illinois
Difficulty
easy
Fitness Level
Suitable for most fitness levels; involves standing and walking up to 1 mile with occasional stairs.
Ready to Explore Chicago?
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