Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

If you’re looking for a memorable way to see Chicago after dark, the Gangsters, Ghosts, and Haunted Hotels Segway Tour offers a unique blend of spooky stories, historic tragedies, and city skyline views—all rolled into a 2-hour glide through the city’s most haunted and notorious spots. We’ve checked out the details to give you a balanced look at what to expect, highlighting the adventure’s strengths and points to consider.

What immediately catches the eye is the chance to zip along Chicago’s illuminated streets while hearing tales of infamous gangsters like Al Capone, ghostly hotel legends, and historic disasters. It’s a fun, slightly chilling experience that’s perfect for night owls, history buffs, or anyone curious about Chicago’s darker stories.

One potential downside is that Segway riding can be tricky for some—a few reviews mention feeling a bit uneasy or unable to finish the tour. This underscores the importance of a proper safety briefing and comfort with the vehicle. Also, it’s not suitable for children under 12 or those with certain health conditions, so check the restrictions beforehand.

This tour suits travelers seeking a light-hearted but atmospheric experience that combines sightseeing with ghost stories. It’s especially appealing for those who enjoy a bit of thrill alongside their city exploration.

Key Points

• Nighttime adventure through Chicago’s most haunted sites and historical disasters
• Professional guides with deep local knowledge and patient instruction
• Beautiful skyline views illuminated at dusk and night, perfect for photography
• Small group size (limited to 8) for a more personalized experience
• Cost-effective at $78, offering a blend of fun, education, and scenic sights
• Safety considerations include weight limits, age restrictions, and the need to wear flat-soled shoes

An In-Depth Look at the Chicago Haunted Segway Tour

The Experience and What Makes It Special

This tour is designed for those intrigued by Chicago’s more macabre side. The route weaves through downtown, taking in iconic sites while telling stories of ghosts, disasters, and gangsters. You’ll be guided by a certified instructor, who provides a comprehensive Segway orientation, ensuring everyone is comfortable before hitting the streets. This setup is crucial, especially since some reviews mention the challenge of feeling safe on the device—so a good guide makes all the difference.

The tour kicks off at the northeast corner of Columbus Drive and Monroe Street, marked clearly by orange flags and signs. From there, you’ll glide through the shadows of the city, passing haunted hotels like the Congress Hotel, known for ghostly tales, and the site of the Iroquois Theatre fire, where over 600 lives were lost.

Expect to visit Death Alley, the site of the Fort Dearborn Massacre, and the location of Chicago’s worst maritime disaster, where 800 perished—a stark reminder of the city’s violent and tragic past. The tour also takes you down to Lake Michigan to see Al Capone’s haunted yacht, a highlight for gangster history enthusiasts.

One of the key strengths is the expert storytelling. The guides share stories of the self-playing pianos in haunted hotels and recount the eerie events that gave these sites their spooky reputations. According to a reviewer, the guides “are very helpful and good at teaching,” which can help ease nerves and make the experience more enjoyable.

The Journey and Stops

The route along Michigan Avenue allows you to enjoy the city lights while listening to ghostly tales. The Chicago River cruise by the tour’s end offers a beautiful backdrop, with the skyline glowing against the night sky. It’s a perfect way to end the tour on a scenic note, especially if you’re a fan of city silhouettes and reflections on the water.

The tour’s duration of 2 hours strikes a good balance—long enough to take in multiple sites and stories without becoming tiresome. The small group size means you get more personalized attention, and questions are encouraged, enriching your understanding of Chicago’s darker history.

The Practicalities and Value

At $78 per person, the price seems reasonable considering the guided storytelling, safety equipment, and the unique experience of touring by Segway. It’s a playful alternative to walking tours, offering a fun way to cover more ground quickly. Plus, the night setting enhances the spooky atmosphere, making it feel like you’re stepping into a ghost story.

The included helmet and thorough orientation are vital for safety, particularly since some reviews mention the initial challenge of controlling the Segway. Not everyone may feel confident, so it’s worth noting that people who are uncomfortable on a Segway or have mobility issues might want to consider other options.

What Some Travelers Say

While most reviews are positive, a couple highlight that not everyone finds Segway riding easy. One traveler mentioned, “Unable to complete the tour. My companion didn’t feel safe using the Segway,” but praised the staff’s patience and helpfulness. This suggests that, despite some initial hurdles, the guides do their best to ensure everyone feels secure.

On the bright side, another guest called it “awesome” and highly recommended it, emphasizing the stunning views and knowledgeable guides. These comments reinforce that the experience’s success hinges on comfort with the Segway and a willingness to enjoy a spooky, scenic city tour.

Who Should Consider This Tour?

This experience is best suited for adventurous travelers who enjoy a mix of history, ghost stories, and city views. It’s great for nighttime explorers, curious about Chicago’s darker past and gangster legends. Those comfortable on a Segway and over 12 years old will get the most out of it.

If you’re seeking a laid-back, educational experience with minimal physical activity, this might not be the perfect fit. However, for families with teenagers, history buffs, and thrill-seekers, it offers a memorable outing.

The Sum Up

The Chicago Gangsters, Ghosts, and Haunted Hotels Segway Tour combines scenic city views with spine-tingling stories that add a layer of intrigue to your evening in the Windy City. The expert guides, engaging storytelling, and beautiful night scenery make it a worthwhile activity for those who enjoy an atmospheric mix of history and legend.

While it isn’t for everyone—particularly those uneasy on a Segway or with certain health concerns—the tour offers excellent value, especially considering the small-group setup and the engaging, authentic stories shared. It’s a fantastic way to experience Chicago’s haunted past while enjoying a fun, active adventure.

Whether you’re a ghost story enthusiast or simply looking for a different way to see the city after sunset, this guided Segway tour provides a lively, spooky journey that leaves a lasting impression.

FAQ

Is this tour suitable for children?
This tour is recommended for travelers over 12 years old. Children under 12 are not allowed due to safety concerns and age restrictions.

What should I wear for the tour?
Wear flat-soled shoes—no sandals or flip-flops—and dress appropriately for the weather. Since bathrooms are limited before the tour, use facilities beforehand.

What if I’ve never ridden a Segway before?
The tour includes a thorough orientation by a certified instructor. Guides are patient and helpful, making sure everyone feels ready before starting.

Can I cancel if my plans change?
Yes, you can cancel up to 24 hours in advance for a full refund, offering flexibility if your plans shift unexpectedly.

Are there any health restrictions?
Yes, participants should weigh between 100 and 260 pounds, not be pregnant, and should not have conditions like seizures, recent joint replacements, or mobility impairments.

What if I don’t feel confident on the Segway?
It’s important to be comfortable riding the device; if not, you might find it challenging to finish the tour. The staff is helpful, but some users may prefer walking or a different type of tour.

In summary, the Chicago Haunted Segway Tour offers a distinctive way to explore the city’s mysterious past, combining scenic nighttime views with storytelling that’s both spooky and educational. It’s perfect for those seeking a lively, active experience that makes the most of Chicago’s haunted reputation—just be sure you’re comfortable on a Segway and eager to hear some ghostly tales.