Step into the darker side of Chicago with a walking tour that mixes true crime, mob legends, and eerie paranormal tales. This journey through the city’s past dives into the hidden corners and whispered stories that shaped Chicago’s reputation for mystery and mischief. From infamous hangouts to sites tied to unexplained events, every stop adds another layer to the city’s shadowy history.

Your guide brings these stories to life with gritty details and insider knowledge, all while leading you through some of Chicago’s most atmospheric streets. Expect a blend of real history, chilling folklore, and the kind of stories that stay with you long after the tour ends. It is an unforgettable way to explore the city for crime buffs, ghost enthusiasts, and anyone who loves a good thrill.

Itinerary

• Death Alley: Visit one of Chicago’s most infamous back alleys, long rumored to echo with restless spirits tied to a tragic theater fire.
• Chicago Theatre: Hear the stories behind this iconic landmark and the paranormal sightings reported by performers and staff.
• Marshall Field and Company Building: Learn about the historic department store’s ties to Chicago’s darker past and the eerie legends that linger within its walls.
• Holy Name Cathedral: Stand at the site of a major mob hit and uncover the violent events that left a lasting mark on the city’s history.
• Biograph Theater: Walk the same streets where notorious outlaw John Dillinger met his end and uncover the truth behind his final moments.
• St. Valentine’s Day Massacre site: Revisit the scene of Chicago’s most infamous gangster clash and hear what really happened that cold February morning.
• The Haunted Congress Plaza Hotel: End at one of Chicago’s most haunted locations, filled with stories of unexplained sightings, mob ties, and lingering spirits.

Any restrictions to participate?

• Age: All age groups are welcome, but this tour includes ghost stories and mob-related history that may be intense for young children.
• Physical limitations: This is a walking tour. Guests should be able to walk approximately 1–1.5 miles at a comfortable pace and stand for periods of time.

Who can you accommodate for?

• Children: Children are welcome, but all participants must have a paid ticket. Parental discretion is recommended due to the tour’s spooky and historical mob content.
• Individuals with disabilities: The tour uses city sidewalks and public areas, which are generally accessible. Some uneven pavement or minor inclines may occur. Service animals are permitted.
• Languages: This tour is conducted in English.
• Pets: Pets are not allowed, except for service animals.

What to expect on the day of the experience?

• Duration: Approximately 2 hours. The experience may run slightly longer based on group pace and engagement.
• What’s included:
  • A guided walking tour exploring Chicago’s mob history, hauntings, and unsolved mysteries
  • Storytelling at notorious locations tied to Al Capone, prohibition-era gangsters, and eerie local legends
  • Visits to historical mob sites and paranormal hotspots
• Who will be present: A professional local guide will lead the tour, along with other guests in the group (typically up to 15–20 participants).
• Spectators: No spectators are allowed; all individuals must have a ticket.
• Photo / video: Photos and videos are encouraged unless specific locations request otherwise.
• Specific rules to follow: Guests must stay with the group, follow city safety rules, and be respectful at historical sites or memorial locations.

How to prepare?

• Weather dependency: This tour runs rain or shine. In cases of severe weather, modifications to the route may occur.
• Arrival: Plan to arrive 10–15 minutes before the scheduled start time to meet your guide.
• Parking: Paid street parking and nearby garages may be available; public transit or rideshare is recommended due to downtown congestion.
• What to wear: Comfortable walking shoes and weather-appropriate clothing. Evening tours may be cooler, so layers are recommended.
• What to bring:
  • Water bottle
  • Phone or camera
  • Weather accessories (umbrella, jacket, hat depending on season)
• Restrooms / lockers / changing rooms: Restrooms are not guaranteed along the walking route. Guests should plan accordingly before the tour begins.

Anything else I should know before going on this experience?

• This tour includes crime stories, ghost legends, and historical accounts of violence; discretion is advised for sensitive guests.
• The tour takes place entirely outdoors along busy sidewalks and streets; attentiveness is important.
• The guide may adjust pacing depending on group size and engagement.

Unused Experience Vouchers can be returned within 14 days for a full refund to the original purchaser, no questions asked.

If you have any unused Experience Vouchers, you can exchange them for anything else in our marketplace, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference, but if you choose one that costs less, you'll receive a credit towards your next booking.

No refunds are allowed once the experience is booked, but you can reschedule up to 24 hours before your experience, for a date within a year of the original booking. To reschedule, contact the experience provider directly. No-shows or rescheduling less than 24 hours in advance means losing the value of your experience.