Small-Group Ghosts And True Crime Walk

Inside Chicago Walking Tours skips the postcard version of the city. Over roughly two hours the guide works through ghost tales, gangster history, and true crime with a small group. The approach lands well: 4.9 stars across 80 reviews, from $35 per person.

Overview

Inside Chicago Walking Tours runs this two-hour walk through the darker chapters of the city's past, from gangsters and restless spirits to local disasters. Most city tours skip the gruesome material. The group is capped at 20 travellers, and reviewers have described the group as engaged and nice.

The walk starts in River North, directly in front of the FedEx store near the corner of Erie and Dearborn, where you check in with your guide. From there the route moves through the city over roughly two hours, with stops tied to gangster hideouts, haunted buildings and pieces of Chicago history that hide in plain sight. Several reviewers mention going inside hotels and restaurants they would never have entered on their own. The tour finishes at the Congress Plaza Hotel on South Michigan Avenue, described by the operator as among the most haunted hotels in the country.

It suits travellers who like history with an edge and do not mind being on their feet. Reviewers frequently praise the guides' knowledge of Chicago history and architecture, and long-time Illinois residents have said they still learned new things. Expect walking at a moderate pace with standing time at each stop.

What's Included

Itinerary

1. Meet in River NorthCheck in with your guide in front of the FedEx store near the corner of Erie and Dearborn, at 34 W Erie St.
2. River North walkThe first hour is spent in River North, hearing stories of gangsters, spirits and disasters tied to the landmarks along the way.
3. Chicago walking sectionThe second hour continues through the city, with reviewers mentioning stretches along the river walk and stops inside hotels and restaurants.
4. End at Congress Plaza HotelThe tour ends near or inside the Congress Plaza Hotel at 520 S Michigan Ave, a building the operator calls the most haunted hotel in the country.

What To Expect From The Tour

A few practical points will help you get the most out of this walk.

• Comfortable shoes. This is a walking tour covering a lot of ground across two hours. One reviewer warned to be prepared to get your steps in. Wear shoes you can walk and stand in comfortably.
• Moderate fitness. The listing asks for a moderate physical fitness level and says the tour is not recommended for travellers with back problems. The distance is real, so factor that in when booking.
• Weather gear. The experience requires good weather, so dress for the forecast. There is no vehicle to retreat to, and the whole route is outdoors between stops.
• Ask questions. Several reviewers describe guides who answered extra questions and ran question and answer moments at stops. Curiosity gets rewarded here, so bring the questions you have about the city's dark history.
• Group feel. The group is limited to a maximum of 20 travellers. Reviewers describe an engaged, conversational atmosphere rather than a lecture.
• Getting there. The meeting point is near public transportation, per the listing. Plan to arrive at the FedEx store on Erie with time to check in with your guide before the start.

Common issues. The tour is not wheelchair accessible, though it is pushchair accessible and service animals are allowed. Gratuities and hotel pickup are not included in the price. One reviewer felt the walk between stops had long pauses and wished more content filled the gaps, and another thought the tour tried to cover too many topics without going deep on any. The route depends on good weather, and poor conditions can mean a cancelled departure, in which case the operator offers a different date or a full refund.

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