Chicago's history isn't all skyscrapers and deep-dish pizza. This walking tour digs into the city's darker chapters, covering true crime, gangster history, and ghost stories along a route that starts north of the river and winds down into the Loop. A handful of historic interiors once frequented by real Chicago gangsters are included along the way.

Covering just under 2 miles at an easy pace, the tour runs largely outdoors and touches on some genuinely unsettling history, including violent crime and past disasters, so it tends to suit older kids and adults more than young children. It's a good fit for true crime fans, history buffs, or anyone who likes their sightseeing with a little edge.

Any restrictions to participate?

• Age: All ages are welcome, though the tour covers mature themes including violent crime, disasters, and disturbing history that may not suit young children
• Physical limitations: Participants should be comfortable walking almost 2 miles, mostly outdoors

Who can you accommodate for?

• Children: All participants must pay to participate, children included
• Individuals with disabilities: Accessibility varies by route; contact experience provider in advance to confirm accessibility for this specific tour
• Languages: Public tours are conducted in English
• Pets: Only service animals are allowed on this tour

What to expect on the day of the experience?

• Duration: 2 hours
• What's included: Guided walking tour with entry to a few historic interiors linked to Chicago's gangster history
• Who will be present: A guide will be present throughout the tour, along with up to 20 total guests
• Photo/video: Photos are allowed and encouraged throughout the tour; a few buildings may restrict specific photo locations
• Specific rules to follow: Guests are asked to silence phone ringers and step aside to take calls; tipping the guide is appreciated but never required

How to prepare?

• Weather dependency: Tours run rain or shine; no refunds are issued for weather-related cancellations by guests, though the operator may cancel and offer a reschedule or refund in extreme conditions
• Arrival: Plan to arrive at least 5 minutes before departure; the tour begins on the north side of the river near Erie and Dearborn Streets and ends in the Loop near Roosevelt University, with exact meeting details provided upon ticket purchase
• Parking: No dedicated parking is provided; public garages and metered street parking are available near the starting point
• What to wear: Comfortable walking shoes and weather-appropriate clothing are recommended, since the tour runs largely outdoors
• What to bring:
  • A phone or camera for photos, with ringers silenced during the tour
  • Weather-appropriate layers or an umbrella if needed
  • Cash for tipping the guide, appreciated but not required
• Restrooms/lockers/changing rooms: The tour does not make a designated restroom stop; guests are encouraged to use restrooms before the tour begins

Anything else I should know before going on this experience?

• This tour covers mature themes, including violent crime, disasters, and disturbing history, and may not be suitable for sensitive guests

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 any other experience in our marketplace, free of charge, no matter when. If you choose an experience that's more expensive, you'll need to pay the difference.

No refunds are allowed once the experience is booked, but you can reschedule up to 72 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 72 hours in advance means losing the value of your experience.