Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

If you’re looking for an evening adventure that combines a bit of thrill, history, and spooky storytelling, the Chicago Gangsters, Ghosts, and Haunted Hotels Segway Tour might just be your perfect fit. Priced at $78 per person and lasting about 2 hours, this guided tour takes you through the heart of downtown Chicago, exploring notorious gangster hideouts, haunted hotels, and sites of tragic disasters — all while cruising effortlessly on a Segway.

What we particularly love about this tour is how it blends a fun, active experience with authentic stories of Chicago’s darker past. The professional guides are knowledgeable and eager to share chilling tales, making the entire ride both entertaining and educational. Plus, the illuminated city skyline at night creates a captivating backdrop that makes the ghost stories come alive.

A possible consideration is that the tour requires participants to stand comfortably for around an hour and a half, and not everyone may feel confident on a Segway, especially if they’re new to it. It’s also essential to arrive 15 minutes early for check-in; late arrivals can’t join in, so punctuality pays off.

This experience suits travelers who enjoy mystery, history, and scenic nighttime city views. It’s especially ideal for those comfortable on a Segway and eager to explore Chicago’s haunted side in a lively, fun way. Families with teenagers, history buffs, and anyone with a penchant for ghost stories will find plenty to enjoy here.

Key Points

• Engaging night tour with a mix of history, ghost stories, and city sights
• Expert-guided with detailed storytelling and local knowledge
• Active, fun experience cruising on Segways through downtown Chicago
• Highlights include haunted hotels, disaster sites, and gangster lore
• Limited group size ensures a personalized experience
• Valuable for those interested in Chicago’s darker past and scenic night views

You can check availability for your dates here:

The Experience in Detail

Starting Off: The Meet-up and Orientation

When you arrive at the meeting point on the NE corner of Columbus Drive and Monroe Street, you’ll notice orange flags signaling the start of your adventure. The staff, including a certified Segway instructor, will give you a thorough orientation—a must for those new to Segway riding or uncertain about balancing. We found this step reassuring, as it helps you feel confident before hitting the streets.

Cruising Through Chicago’s Historic Streets

Once geared up, you’ll glide through the downtown Loop, where the city’s illuminated skyline provides a stunning backdrop against the evening sky. The tour guides tell stories as you zip along Michigan Avenue, making each pause a chance to learn about Chicago’s notorious gangsters, disasters, and haunted landmarks.

Haunted Fort Dearborn and the Ghostly Hotels

One of the tour’s most atmospheric stops is the Haunted Fort Dearborn, where legends tell of ghostly apparitions and unexplainable events. We loved the way the guide brought history alive with vivid storytelling, creating a sense of mystery that lingered even after we moved on.

The Congress Hotel, often called the most haunted hotel in Chicago, is another highlight. Guides share tales of ghost sightings and eerie piano music, adding a layer of supernatural intrigue to your evening. The self-playing piano accounts in reviews highlight how hauntingly alive the hotel’s reputation is.

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Tragedy and Disaster Sites

The tour doesn’t shy away from Chicago’s more grim chapters. You’ll pass by the site of the Eastland Disaster, where over 800 lives were lost, and cruise along the River Walk past Death Alley, the tragic scene of the Iroquois Theatre fire that claimed over 600 lives in a single day. Guides explain these events with sensitivity, making their stories both somber and captivating.

The Gangs and the Yacht

A special feature is a visit to Al Capone’s haunted yacht on Lake Michigan. The guide recounts tales of the gangster era, giving a glimpse into Chicago’s prohibition-era nightlife filled with danger and intrigue. From the boat, you get a stunning view of the city skyline, which looks especially dramatic as the lights reflect on the water.

The Final Stretch: The Chicago River and the City Lights

As you cruise along the Chicago River, the illuminated bridges and skyscrapers make a magical setting. The tour concludes with a view of Fort Dearborn, tying the tour’s stories to the city’s historic roots.

The Practicalities

The tour includes helmets, a professional guide, and a Segway orientation to ensure safety and comfort. It’s limited to 8 participants, which means plenty of personalized attention. The cost is quite reasonable considering the mix of active fun and rich storytelling, offering excellent value for an evening of entertainment and education.

A couple of reviews highlight the importance of proper footwear and being comfortable on a Segway. One reviewer mentioned that their companion didn’t feel safe using the Segway, which underscores the need for some confidence on the device. Also, note that pregnant women, children under 12, and those with mobility issues are not permitted.

The meeting point is straightforward to find, with clear signage and staff ready to help. Arriving 15 minutes early is vital, as latecomers cannot join the tour.

Authentic Traveler Insights

From the reviews, it’s clear that guides like Tammy make the experience memorable, providing great details and a friendly attitude. One traveler noted that the city looks stunning at night and that this tour is a great way for families with teenagers to explore Chicago in a different light. Another reviewer appreciated the knowledgeable guides and the scenic views.

However, not everyone felt completely comfortable on the Segway, reminding us that it’s best suited for travelers who are willing to stand and balance for the duration. The spooky stories and stunning city views seem to compensate for this, creating a perfect balance of fun and fright.

Final Thoughts

This Ghosts and Gangsters Segway Tour offers a unique way to see Chicago’s historic and haunted sites in just a couple of hours. Its blend of active sightseeing, storytelling, and atmospheric scenery makes it an engaging experience for a wide range of visitors. The small group size and professional guides ensure a personalized and safe outing.

If you’re a history buff with a curiosity about Chicago’s darker legends or a traveler looking for a fun, active night out, this tour fits the bill. It’s particularly suitable for those comfortable on a Segway and eager for stories that mix fact with a touch of ghostly legend.

FAQ

• Is the tour suitable for children?
  It’s best for ages 12 and up, as younger children may find balancing on a Segway challenging or unsafe.

• How long does the tour last?
  The experience runs approximately 2 hours.

• What should I wear?
  Wear flat, closed-toe shoes. Avoid sandals or flip-flops for safety.

• Are helmets provided?
  Yes, helmets are included.

• What if I don’t feel comfortable on the Segway?
  The guides provide a thorough orientation, but if you’re unsure, it’s best to assess your comfort level beforehand.

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

• Is the tour available at night?
  Yes, it’s primarily an evening experience, perfect for enjoying Chicago’s skyline and spooky atmosphere.

• How many people are in each group?
  Limited to 8 participants for a more personalized experience.

• Are there any restrictions for pregnant women?
  Yes, pregnant women are advised not to participate.

• Where do I meet the tour?
  At the NE corner of Columbus Drive and Monroe Street, with clear signage and staff ready to guide you.

This tour offers a lively, memorable way to explore Chicago’s haunted past while enjoying the city’s vibrant nightscape. Whether you’re a ghost story enthusiast or just looking for a fun activity, it’s a ride that promises intrigue and a bit of adrenaline—just what a city like Chicago can deliver.

You can check availability for your dates here: