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Explore Chicago’s haunted past and infamous gangsters on this 1.5-hour walking tour featuring speakeasies, mob sites, and ghost stories for $35.

The Haunted Chicago: Crime and Ghosts Walking Tour offers a captivating look into the city’s dark history, notorious gangsters, and paranormal legends. Priced at $35 per person, this 1 hour 30 minute excursion guides you through Chicago’s Prohibition-era speakeasies, mob shootouts, and ghostly hotspots. The tour departs from 238 N State St and ends near 78 E Washington St, making it easy to include in a day of sightseeing or evening plans.
With a highly-rated guide who provides rare insights, this tour appeals to those intrigued by true crime, ghost stories, and Chicago’s hidden history. The small group of up to 20 travelers ensures an intimate experience, while the mobile ticket makes access straightforward. While the tour involves walking about a mile over 1.5 hours, it’s a perfect choice for visitors seeking a compact, engaging look at Chicago’s shadowy past.
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The tour kicks off at 238 N State St, where an expert guide meets the group. This initial stop offers an introduction to Chicago’s architecture and ghostly tales along the Chicago River. The guide explains the haunted history intertwined with the city’s impressive riverfront buildings, setting a mysterious tone for the walk ahead.
This first stop lasts around 15 minutes and includes admission tickets that allow entry to some of the buildings. It’s an engaging introduction that sets the stage for stories of mobsters and supernatural activity linked to the city’s renowned structures.

Next, the tour ventures into River North, known for its Prohibition-era bars. Here, visitors see buildings that once operated as secret speakeasies, offering a glimpse of Chicago’s underground nightlife during the 1920s. The guide points out famous spots associated with notorious criminals like John Dillinger.
This part of the walk lasts about 15 minutes and provides free admission. It’s a prime chance to learn how illegal alcohol trade and mob activity shaped the city’s nightlife and left traces still visible today.

Next, the group visits The Picasso, where they get to interact with the world’s largest Picasso sculpture. Here, the guide discusses corruption in Chicago and explores ghost stories linked to the nearby Chicago Theater District.
This stop offers a mix of art, history, and paranormal tales in roughly 15 minutes. It’s a visually striking location that fuels stories of haunted theaters and eerie sightings in the city’s cultural hotspots.

The tour then goes underground to the Chicago Pedway, where historically significant criminal activity took place, including a famous 1920s gangster ‘whack’. Walking through this hidden network, travelers learn about Chicago’s gangster era, when mob violence and turf wars were common.
This part lasts 15 minutes with free admission, immersing visitors in the seedy underbelly of Chicago’s criminal past. The Pedway’s secretive atmosphere adds a tangible sense of danger and history.

The group continues to Millennium Park, where stories of ghostly apparitions at the Art Institute and haunted hotels fill the air. The guide shares paranormal activity reports from some of Chicago’s most famous landmarks, blending art, architecture, and haunted legends.
This 15-minute stop offers a chance to connect Chicago’s modern landmarks with its spectral tales, making it as much about local legends as historic facts.

Finally, the tour concludes with a brief walk to the Chicago Cultural Center, just a 5-minute stroll from the starting point. Here, the guide wraps up with true crime stories and additional recommendations for exploring Chicago’s haunted and criminal history.
The tour ends at 78 E Washington St, where travelers can continue sightseeing or head to nearby attractions. This last 15-minute segment ensures a satisfying close, with the guide available for any questions or tips.

Throughout the tour, visitors get inside access to notable hotels and landmarks associated with Chicago’s mobsters and ghost stories. These include famous hotels that have hosted notorious figures and sites of historic crimes. Such access enriches the experience, making it more immersive than just viewing from the outside.
Reviews highlight Andre, the guide, as a knowledgeable and energetic storyteller. He explains architecture, crime lore, and ghost stories with enthusiasm, making the tour both informative and entertaining. Guests note that Andre’s storytelling keeps the group hooked and that he provides rare insights into Chicago’s haunted past.
This tour operates with a maximum of 20 travelers, ensuring a personal experience. It’s suitable for most people, with service animals allowed and near public transportation options. The walking distance is approximately one mile over the course of 1.5 hours, making for a manageable pace.
Booking is straightforward with a mobile ticket, and free cancellation is available up to 24 hours in advance, offering flexibility for last-minute plans or changes.
Unlike generic city tours, this experience combines Chicago’s haunted legends with its crime history, focusing on notorious gangsters and paranormal tales. The inside access to historic sites and the expert storytelling make it a standout for those interested in true crime, ghost stories, and the city’s underground history.
The Haunted Chicago: Crime and Ghosts Walking Tour offers an engaging, well-structured look into Chicago’s dark side. It’s ideal for visitors who want a short, lively, and informative experience blending history, crime, and ghost stories. The $35 price point provides good value, especially with inside access and expert narration.
While the tour covers famous landmarks and hidden sites, it remains a walking experience, so those with limited mobility should consider the physical effort involved. This tour is a great way to see a different side of Chicago that most visitors overlook, especially if you enjoy stories of mafia legends, haunted buildings, and spooky legends.
“Andre was extremely formative and enthusiastic, fun to listen to. We thoroughly enjoyed this interesting tour. Highly recommend this tour. He expl…”
Is this tour suitable for all ages?
Most travelers can participate, but the tour involves walking and stories about crime and ghosts, so it may not be ideal for very young children.
How long does the tour last?
The tour is approximately 1 hour 30 minutes long.
Where does the tour start and end?
It begins at 238 N State St and ends near 78 E Washington St, a 5-minute walk from the start.
Are tickets included for the stops?
Yes, the tour includes admission tickets for certain stops, such as the Chicago River and the Chicago Cultural Center.
Is the tour accessible by public transportation?
Yes, the tour location is near public transit options.
Can I cancel my booking?
Yes, free cancellation is available if canceled at least 24 hours before the tour.
What if I have a service animal?
Service animals are allowed on this tour.
What’s the guide’s storytelling style?
Guests praise Andre’s animated and enthusiastic narration, making the stories both informative and entertaining.
Is there a recommended clothing or footwear?
Comfortable walking shoes are advised due to the walking involved.
Can I join this tour last minute?
Yes, as long as there are available spots, you can book via the mobile ticket system.