Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

If you’re looking for a night out that mixes thrills with a dash of history—and a little spooky fun—this Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour might just be what you need. While I haven’t personally rolled along Chicago’s shadowy streets on a Segway, this experience consistently catches attention for its engaging storytelling and scenic nighttime views.

What I really like about this tour is how it transforms a city known for its architecture and lively nightlife into a setting for tales of murder, mayhem, and ghostly apparitions. Plus, the guide’s knowledge makes the experience both immersive and entertaining. However, it’s worth noting that this kind of adventure isn’t for everyone—especially if you’re uneasy on a Segway or have mobility restrictions.

All in all, this tour will suit travelers who enjoy storytelling, history, and a bit of adrenaline, especially those eager to see Chicago from a fresh, slightly spooky perspective.

Key Points

• Nighttime adventure with scenic views of Chicago’s illuminated skyline
• Engaging guides who share chilling stories and historical details
• Eerie stops at haunted hotels, Death Alley, and sites of tragic disasters
• Smooth Segway ride suitable for most but with specific weight and mobility requirements
• Great option for those interested in ghost stories and gangster tales
• Two hours of fun, with a mix of history and fright

You can check availability for your dates here:

An Overview of the Chicago Haunted Segway Tour

This 2-hour guided tour offers a unique way to explore some of Chicago’s most notorious and haunting spots after dark. The experience is designed for those who enjoy both history and a touch of the supernatural, making it a great evening activity, especially if you’re tired of daytime sightseeing.

Pricing is set at $78 per person, which, considering it includes a thorough Segway orientation, helmets, and a professional guide, feels reasonable for a memorable night out. The small group size—limited to 8 participants—means you’ll get personalized attention, which is especially helpful if you’re new to riding a Segway or nervous about the experience.

What Makes This Tour Stand Out?

The highlight is definitely the combination of scenic city views and spooky storytelling. As you glide along Chicago’s streets, you’ll pass by historic sites with dark tales—like Haunted Fort Dearborn, Death Alley, and the site of the Eastland Disaster. These stops aren’t just visual; they’re filled with stories of grim deaths, ghostly sightings, and infamous gangsters like Al Capone.

The tour’s nighttime setting adds a layer of atmosphere that daytime sightseeing just can’t match. The city’s lights flickering against the dark urban landscape lend a mysterious vibe that immerses you in the stories.

What to Expect from the Experience

Starting at the office located at the NE corner of Columbus Drive and Monroe Street, you’ll check in about 15 minutes early. After a quick safety briefing and Segway tutorial from a certified instructor, you’ll set off on your ghostly journey.

Your guide will lead you through Chicago’s shadows, sharing tales of infamous gangsters, suicides, and disasters as you cruise along well-known streets and lesser-known alleys. Expect to hear about:

• Haunted Fort Dearborn, a site with a long history of ghost sightings and tragic events.
• Death Alley, the location of the Iroquois Theatre fire, which claimed over 600 lives in a single day.
• The site of Chicago’s maritime disaster where 800 people perished—an event that still echoes through local lore.
• The Eastland Disaster, one of the city’s worst maritime tragedies, with stories of the lost lives and ghostly apparitions.

Plus, you’ll get a glimpse of Al Capone’s haunted yacht on Lake Michigan and pass by a hotel reputed to be the city’s most haunted, complete with stories of unexplainable piano music and ghostly visitors.

The Route and Stops

While the exact route may vary, what’s consistent is the focus on dark history and haunted sites. You’ll glide through downtown Chicago, including the Loop, along the Chicago River, and down the River Walk—each area providing a different backdrop for ghost stories.

Some reviews note that guides provide excellent details—one reviewer mentioned Tammy, who left them wanting more with her storytelling, and that she helped navigate effortlessly through the city. That kind of personal touch really boosts the overall experience.

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The Practical Side: What You Should Know

The tour is suitable for most people over 12 years old and within the weight limits (100 to 260 pounds). It’s important to wear flat, sturdy shoes—no sandals or flip-flops—and arrive early to check in and get comfortable with the Segway.

Participants should be comfortable standing for around two hours, and those with certain health issues—like pregnancy, recent joint replacements, seizure disorders, or mobility impairments—are advised not to participate.

The group size is limited to ensure safety and personalized guidance, which is a big plus. The tour operates in the evening, giving you that authentic nighttime atmosphere, and cancellation is flexible up to 24 hours in advance.

Experience Tips

• Bring a jacket, as evenings can be cool, especially near the water.
• Use the bathroom beforehand, as the facilities near the office are temporarily closed.
• Listen carefully during the safety briefing—it’s crucial for a smooth ride.

The Value of the Tour

At $78, this experience offers a lot of bang for your buck. Considering it’s a guided tour on a fun mode of transport, it’s a different way to see the city’s haunted side. The fact that you get a small group and a knowledgeable guide makes it feel personal and engaging.

The reviews reinforce this: one reviewer called it “pretty great,” with a guide who provided “a lot of great details,” and the city at night being a “really pretty” backdrop for the stories. Another reviewer, however, mentioned that a companion didn’t feel safe on the Segway, highlighting the importance of comfort with the ride.

Overall, if you enjoy stories of ghosts and gangsters and want to see Chicago from an unusual perspective, this tour is a solid choice.

Who Would Love This Tour?

This experience is perfect for history buffs who like spooky tales, adventure seekers comfortable on a Segway, or anyone wanting a memorable night exploring Chicago’s darker stories. It’s especially appealing for those who appreciate scenic views and engaging guides who bring stories to life.

Travelers who prefer a slower-paced or more physically demanding activity might find this a little less suited, but for most, the two-hour ride offers a nice mix of fun and learning.

The Sum Up

The Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour offers a distinctive way to explore the city’s haunted past after sunset. It combines the thrill of riding a Segway with captivating storytelling about Chicago’s most infamous and eerie sites. The guided experience ensures you’re never lost and always informed, making it a great choice for those who enjoy a good ghost story paired with city views.

While not suitable for everyone—particularly those uncomfortable on a Segway or with certain health conditions—the tour’s small group size and knowledgeable guides make it a worthwhile option for many travelers. Whether you’re a history lover, a mischievous ghost hunter, or just after a fun night activity, this tour could be a highlight of your Chicago trip.

Just remember to arrive early, wear the right shoes, and be prepared for a slightly spooky, scenic ride through the city’s shadows.

FAQs

Is this tour suitable for kids?
It’s designed for participants over 12 years old, and younger teens can join if accompanied by an adult. Children under 12 are not permitted.

Do I need to have experience riding a Segway?
No, a thorough orientation is included, and the guide will help you get comfortable with the Segway before starting.

Are there any physical requirements?
Yes, participants should weigh between 100 and 260 pounds and be able to stand for about two hours. Those with mobility issues or certain health conditions should consider this before booking.

What should I wear?
Wear flat, closed-toe shoes—no flip-flops or sandals—plus a jacket if it’s cool.

Is the tour offered in other languages?
The tour is conducted in English.

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

What if I’m worried about safety?
The tour includes a safety briefing, helmets are provided, and the group size is small for better guidance. If you’re hesitant or uncomfortable, discuss your concerns with the guide before starting.

If you’re after an evening adventure that blends history, ghost stories, and scenic views, this Segway tour could be just the ticket. It’s a fun, different way to see Chicago’s spooky side—perfect for thrill-seekers and story lovers alike.

You can check availability for your dates here: