Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

Exploring Chicago after dark takes on a thrilling new dimension with the Gangsters, Ghosts, and Haunted Hotels Segway Tour. Priced at $78 per person and lasting 2 hours, this tour offers a lively mix of spooky tales, historic tragedies, and city views, all from the unique vantage point of a Segway. Guided by professional guides, the tour combines fun, education, and chills, making it a perfect choice for those interested in Chicago’s darker side.

The tour operates in the evening, allowing participants to enjoy the illuminated city skyline while cruising through iconic neighborhoods. With a small group limit of 8 participants, the experience remains intimate and engaging. It’s especially suited for travelers who enjoy a mix of history, ghost stories, and active outdoor activities—though certain physical requirements and restrictions apply.

Key Points

• Two-hour nighttime Segway tour exploring Chicago’s haunted sites and historic disasters.
• Priced at $78 per person, includes helmet and orientation with a certified instructor.
• Guided visits to Haunted Fort Dearborn, Death Alley, and the Congress Hotel.
• The tour features stories of gangsters like Al Capone, and disasters like the Eastland Disaster.
• Enjoy views of the Chicago skyline illuminated at night while cruising on the Chicago River and River Walk.
• Small group experience with a maximum of 8 participants for personal attention.

You can check availability for your dates here:

Starting Point and How to Find It

The meeting point for this tour is at the NE corner of Columbus Drive and Monroe Street. Tour operators display orange flag signs marked “Segway Tours,” and the office is located one level below street level. Look for orange A-frame signs with arrows directing you to the entrance. It’s recommended to arrive 15 minutes early for check-in, as late arrivals cannot join the tour.

How the Tour Explores Chicago’s Haunted History

This nighttime Segway adventure takes you through downtown Chicago, where you’ll visit the most frightening ghosts and sites of tragic disasters. Stops include the Haunted Fort Dearborn, the site of the Eastland Disaster, and Death Alley, known for the Iroquois Theatre fire that claimed over 600 lives. These locations are central to Chicago’s haunted lore and provide a chilling backdrop for storytelling.

The guide shares gruesome tales about Al Capone’s yacht, which is reputed to be haunted, and discusses the most fearsome hotel in the city, alleged to be haunted with stories of unexplainable deaths and a self-playing piano. These stories add a spooky dimension to the city’s historic sites, making the ride both fun and educational.

The Route Along Michigan Avenue and Downtown

A highlight of this tour is zipping along Michigan Avenue, where you’ll hear spooky stories about the city’s iconic streets. The tour continues through the Loop, offering a chance to see the city’s illuminated skyline while being entertained by the professional guides. The combination of cruising and storytelling makes for a lively and memorable experience.

The route takes you down to Lake Michigan, where you can view Al Capone’s haunted yacht, adding a maritime element to the ghostly tales. The tour also passes by a hotel believed to be the most haunted in Chicago, and moves along the River Walk, giving you a chance to see the site of the Fort Dearborn Massacre.

The Stops at Chicago’s Most Notorious Sites

One of the tour’s main attractions is visiting Death Alley, the location of the Iroquois Theatre fire, where over 600 Chicagoans perished in a single day—a tragic event etched into the city’s history. The tour also takes you past the Chicago River, where 800 people perished in the worst maritime disaster in Chicago’s history.

The route culminates at the Fort Dearborn site, where the massacre that saw the deaths of many early settlers took place. These stops are chosen for their historical importance and their connection to Chicago’s ghostly lore, making for stories that are both chilling and educational.

More Great Tours Nearby

The Practical Aspects: Safety and Group Size

All participants are provided with helmets and receive a thorough orientation from a certified Segway instructor. The small group size of up to 8 participants ensures personalized attention and safety. Participants must sign a waiver, and restrictions include a minimum weight of 100 pounds and a maximum of 260 pounds. The activity is not suitable for pregnant women, children under 12 years, or those with certain health conditions.

Participants should avoid sandals, flip flops, pets, luggage, alcohol, or drugs. The tour route includes bathroom stops, and travelers are advised to wear flat-soled shoes. The meeting point is easy to find, and call assistance is available if needed.

The Experience with Guides and Stories

The guides lead the tour with a focus on storytelling and city history, weaving ghost tales and disasters into the ride. Guides are praised for their knowledge, with some reviews highlighting Tammy as a particularly helpful and detailed guide. The stories of ghostly sightings, murder, and disasters are delivered with enthusiasm, making the tour entertaining for teenagers and adults alike.

The pace of the tour is balanced to allow for safety and storytelling, and riders enjoy the nighttime city views as the skyline glows in the evening light. The combination of active transportation and fascinating stories creates an engaging experience that’s both fun and informative.

Limitations and Considerations

While the tour is highly rated overall, some participants have noted that not everyone feels comfortable using a Segway. One review mentions a companion who did not feel safe, though staff was helpful and patient. Participants should weigh their comfort with Segways and physical restrictions before booking.

The activity is not suitable for pregnant women, individuals with seizure disorders, recent joint replacements, or those unable to stand for over an hour. Late arrivals are not permitted to join the tour, so punctuality is important.

Who Will Love This Tour?

This haunted Segway tour appeals most to those who enjoy history, ghost stories, and active exploration. It’s a great option for families with teenagers, as it combines fun and education with easy transportation. Visitors looking for an evening activity that offers city views and spooky tales will find this tour engaging.

Chicago’s Haunted Secrets on a Segway

This tour offers a distinctive experience by blending Chicago’s dark past with the thrill of riding a Segway. It stands out for its focus on disasters, gangsters, and haunted sites, providing a comprehensive yet entertaining look at the city’s most chilling stories.

While some may find the physical requirements strict, those capable of riding a Segway will enjoy the personalized storytelling and fast-paced route. It’s an exciting way to see Chicago’s nighttime skyline while uncovering its ghostly legends.

Frequently Asked Questions

Is this tour suitable for children?
Participants must be over 12 years old with a minimum weight of 100 pounds. Children under 12 cannot participate.

What should I wear?
Wear flat-soled shoes and avoid sandals or flip flops. Dress for the weather and bring any necessary personal items, but luggage or large bags are not allowed.

Is the tour safe for beginners?
Yes, the tour begins with a thorough orientation from a certified instructor. The small group size helps ensure safety and personalized guidance.

Can I cancel or reschedule?
Yes, the tour offers free cancellation up to 24 hours in advance. You can reserve now and pay later for flexibility.

What are the main highlights of the tour?
Major stops include Haunted Fort Dearborn, Death Alley, Al Capone’s yacht, and a haunted hotel. You’ll also enjoy city views along Michigan Avenue and the River Walk.

Are there any physical restrictions?
Participants need to weigh between 100 and 260 pounds and be able to stand for over an hour. Those with seizures, joint replacements, or who are pregnant should not join.

What is the tour duration?
The entire experience lasts 2 hours, typically in the evening, making it easy to fit into an evening schedule.

What is included in the price?
The fee covers helmet and Segway orientation, as well as the guides. Gratuities are not included.

How do I find the meeting point?
Look for orange flags at the NE corner of Columbus Drive and Monroe Street. The office is one level below street level with orange A-frame signs guiding you.

What makes this tour unique?
Its combination of ghost stories, historic disasters, and riding through illuminated city streets on a Segway makes for an entertaining and spooky way to experience Chicago at night.

You can check availability for your dates here: More Great Tours Nearby