Chicago Segway Tour: Haunted Crime & The Outfit

Chicago Segway Tour: Haunted Crime & The Outfit — A Deep Dive

Imagine gliding effortlessly through Chicago’s illuminated streets, hearing chilling tales of murder, gangsters, and ghosts—all from the saddle of a Segway. That’s precisely what the Haunted Crime & The Outfit tour promises. While we haven’t taken it ourselves, the reviews and detailed itinerary paint a compelling picture for those who love a mix of history, spooky stories, and a bit of adventure.

What we really appreciate about this experience is how it combines practical sightseeing with engaging storytelling. First, it offers a fun, active way to see more of the city than you could on foot—covering ground quickly, with the added thrill of a Segway. Second, the guides seem to bring the stories to life with humor and knowledge, making the tour both educational and entertaining. One potential consideration? Since the tour operates in all weather conditions, you’ll want to dress appropriately for Chicago’s unpredictable weather.

This tour is ideal for travelers who enjoy tales of Chicago’s darker past, want a unique way to see the city’s nightlights, and are comfortable on a Segway (or eager to learn). It’s especially good for small groups looking for a personalized experience with expert guides.

Key Points

• Mix of haunted stories, gangster lore, and iconic Chicago landmarks
• Efficiently cover more ground than walking, ideal for a quick but rundown
• Small group sizes ensure personalized attention and safety
• Guides are knowledgeable, funny, and passionate about Chicago’s history
• Tours operate in all weather, so dress accordingly
• Cost offers good value for the experience, safety gear, and guide expertise

An Introduction to the Haunted Chicago Segway Tour

If you’re looking for a memorable way to explore Chicago at night, this Segway tour is a clever choice. It’s a perfect blend of adventure, history, and ghost stories. The tour is designed to be fun and informative, with a focus on some of the city’s most notorious crimes, disasters, and haunted sites.

What sets this tour apart is its unique theme—it’s not just about sightseeing but about uncovering Chicago’s darker side. The fact that it covers more ground than a walking tour means you’ll get to see a lot in a short time, which is perfect for travelers with limited schedules or who want to maximize their experience.

Two things we love are the guides’ ability to make history lively and the safety focus, including thorough Segway orientation and helmets. However, since it’s weather-dependent, you’ll want to be prepared for rain or cold. This tour is best suited for those curious about Chicago’s haunted past, comfortable on a Segway, and looking for a lively evening activity.

What to Expect from the Itinerary

Starting Point: Absolutely Chicago Segway Tours at 300 E Monroe St

You’ll need to arrive 15 minutes early to check in, fill waivers, and get fitted with helmets. The initial 15 minutes are dedicated to a video and detailed training session. This ensures everyone, even the most nervous, feels confident on the Segway. Reviewers consistently praise the instructors’ patience and clarity—”Tammie was great! It was a great evening riding through Chicago learning a ton of history,” writes one happy rider.

First Stop: Introduction and Safety Briefing

The tour begins with a comprehensive orientation, making sure even beginners are comfortable. Most guests find the Segways quite user-friendly after a few minutes of practice, especially with the guide’s support.

The Heart of the Tour: Haunted Sites and Crime Stories

The primary appeal here is the stories of death, disaster, and gangsters that have haunted Chicago’s streets. As you glide past iconic landmarks, your guide shares tales—sometimes spooky, sometimes grisly—that add layers of context to the nighttime cityscape.

Landmarks Lit Up at Night

While the route isn’t explicitly detailed in the overview, you can expect to see some of Chicago’s most famous sights glowing under the night sky. The magic of touring at night is that the city’s lights cast an eerie glow over the architecture, amplifying the haunted ambiance.

Small Group Experience

With a maximum of 8 travelers per tour, your guide can give personalized attention. A reviewer remarked, “Most importantly, I felt very safe with her, and she constantly communicated hazards,” emphasizing the value of small-group safety and interaction.

Duration and Pacing

At just about two hours, the tour is a lively but manageable experience. You’ll cover more ground than on foot, making it easier to get a broad view of the city’s architecture and stories without feeling rushed.

The Value of the Experience

At a price of $75.48 per person, this tour offers a lot of bang for your buck. It includes a Segway orientation, helmets, and a personal bag—all essentials for comfort and safety. The guides’ enthusiasm and knowledge also add significant value, transforming what could be a simple ride into an engaging, story-filled evening.

Many reviews highlight the excellent guides, like Jeremy, Kevin, and Tammie, noting they’re both knowledgeable and funny. One reviewer said, “The experience is one of a kind,” emphasizing how this tour stands out from typical sightseeing.

The small group size is another advantage, ensuring you’ll get attention, clarification, and a more personal connection. It’s also a flexible experience—operating in all weather—so be prepared for Chicago’s variable climate.

Detailed Breakdown of the Tour Experience

The Starting Point

Arriving 15 minutes early, you’ll check in at the tour headquarters in downtown Chicago. Here, safety gear is fitted, waivers are signed, and everyone gets a quick rundown. Think of this as your warm-up—both for the equipment and the stories you’re about to hear.

The Training Session

The training is straightforward: a video and one-on-one coaching to ensure everyone feels comfortable riding a Segway. Reviewers consistently praise the instructors’ patience and ability to build confidence, even among first-timers. Expect about 15 minutes of instruction, which is more than enough for most guests to get the hang of it.

Glide Through the Night

Once underway, you’ll follow your guide through Chicago’s illuminated streets. The small group size makes the experience intimate. Expect to see sites lit up beautifully after dark, providing a different perspective than daytime tours.

Haunting Stories and Crime Tales

Every stop features compelling stories—ranging from tales of gangsters like those associated with “The Outfit,” to tales of disasters and ghosts lurking in the shadows. One reviewer noted, “Our guide Carrie was hilarious and made our tour truly memorable,” which shows how engaging and lively the storytelling can be.

Landmark Highlights

While the exact route isn’t specified, you might pass by notable historical sites, with the guide offering colorful commentary. The combination of lighting, architecture, and ambient noise at night creates an immersive, slightly spooky atmosphere.

End of Tour

After about two hours, the tour concludes back at the starting point. Many participants say they leave feeling like they’ve uncovered a different layer of Chicago—an electric mix of history and haunting tales.

What We Think About the Price and Overall Value

For about $75, you get an interactive experience with expert guides, safety gear, and the ability to see large parts of Chicago efficiently. Compared to traditional tours, this offers both active fun and educational storytelling. The reviews indicate the guides’ passion and humor greatly enhance the value, making it worth the price for many.

Who Would Enjoy This Tour?

This experience suits adventure-loving travelers eager to see Chicago from a new perspective. It’s ideal for those who enjoy stories of crime and ghosts and are comfortable on a Segway. It’s also perfect for small groups or couples looking for a memorable night activity. Keep in mind, minimum age is 12, and there’s a weight requirement (minimum of 100 pounds, maximum 260 pounds). Those who dislike riding in potentially rainy or cold weather might want to plan accordingly.

The Sum Up

The Haunted Crime & The Outfit Segway tour offers a distinctive way to explore Chicago’s nighttime streets, combining fun, history, and a ghostly twist. The guided storytelling adds depth to the sights, making it much more than a simple ride around town. The small group setting ensures a relaxed, personalized experience, while the efficient coverage allows you to see more in less time.

If you’re interested in Chicago’s darker side, enjoy an active outing, and like a good story, this tour could be just the ticket. The guides are praised for their knowledge and humor, making the experience both educational and entertaining. Plus, it’s a fantastic way to add some spooky flair to your Chicago trip—especially if you’re traveling with others who enjoy a bit of ghostly intrigue.

In short, a well-organized, engaging, and memorable experience that is especially appealing during the cooler months or at night when the city’s lights and shadows come alive. Just dress for the weather, arrive early, and prepare for a fun ride through Chicago’s haunted past.

FAQs

Is prior Segway experience necessary? No, the tour begins with a comprehensive orientation and training session, making it accessible even for first-timers.

What is included in the tour price? The tour includes a certified guide, thorough Segway orientation, helmet, and a bag for personal belongings.

Can I cancel if my plans change? Yes, you can cancel for free up to 24 hours before the tour, with a full refund.

What should I wear? Dress appropriately for weather conditions, as the tour operates rain or shine.

What is the group size? Tours are small, with a maximum of 8 travelers, ensuring personalized attention and safety.

Are there age or weight restrictions? Yes, minimum age is 12, minimum weight is 100 pounds, and maximum is 260 pounds.

This detailed review aims to give you a clear picture of what to expect from the Haunted Crime & The Outfit Segway tour in Chicago. Whether you’re a history buff, a ghost story enthusiast, or just looking for a fun way to explore the city at night, this experience offers a lively, memorable adventure.