Chicago Segway Tour: Haunted Crime & The Outfit

Chicago Segway Tour: Haunted Crime & The Outfit offers an unusual way to see the Windy City’s darker side. For around $75, you get about two hours of gliding through illuminated streets, uncovering stories of disasters, murders, and gangsters that shaped Chicago’s reputation. Led by a friendly, knowledgeable guide—often dressed in costume—this tour combines a ghostly narrative with the thrill of riding a self-balancing scooter.

What we love most is how efficiently the Segway allows you to cover more ground than you would on foot, making it ideal for those who want to see many sites without tiring out. Plus, the storytelling is lively and engaging, bringing to life the city’s haunted episodes with humor and clarity. It’s a fantastic evening activity that balances fun with education.

One thing to consider: weather conditions can affect your experience, so dressing appropriately is a must, especially since most reviews mention the tour operates rain or shine. It’s best suited for travelers who enjoy quirky history, lively guides, and the chance to see Chicago by night in a unique way. If you’re a lover of ghost stories or gangster lore, or simply want a fun, active way to explore the city’s hidden stories, this tour fits the bill.

Key Points

• Unique Exploration: Glide more easily and quickly through Chicago’s night streets—covering landmarks and haunted sites effortlessly.
• Engaging Guides: Friendly, knowledgeable guides, often dressed in costume, add humor and insights that bring history to life.
• Stories of the Dark Side: Learn about infamous tragedies like the 1903 Iroquois Theatre fire, maritime disasters, and gangster murders.
• Safety & Comfort: Helmets and a comprehensive orientation ensure even nervous riders feel confident.
• Small Group Experience: Limited to 8 travelers, ensuring personal attention and a friendly atmosphere.
• Ideal for Night Owls: The illuminated cityscape at night adds extra magic to the experience.

Exploring the Haunted Chicago Segway Tour in Detail

Starting Point and Orientation

The adventure begins at 300 E Monroe St, a central and convenient location in downtown Chicago. Arrive at least 15 minutes early to check in, fill out waivers, and get fitted with your helmet. The tour kicks off with a short video and a personalized Segway training session. This is especially reassuring if it’s your first time—our guides, like Jeremy or Shawn, are praised for their patience and clear instructions, making even the most hesitant rider feel at ease.

What Makes the Training Important?

Many reviews highlight the importance of the thorough orientation. As one traveler noted, “the practice session made sure we were all comfortable before starting the tour,” which helps prevent any jitters during the actual ride. This is key, because riding a self-balancing scooter can seem daunting at first, but with good instruction, you’ll soon feel like a pro.

The Ride and Its Stops

Once everyone is comfortable, your group zooms off into the Chicago night, visiting a series of sites famous—or infamous—for their tales of tragedy and mystery.

Iroquois Theatre Fire: The tour stops at the alley where over 600 lives were lost in 1903. The tragedy is a reminder of Chicago’s past risks, and the stories told here are often vivid and chilling.

Michigan Avenue Hotel Ballroom: Standing in this elegant space, you might listen for the ghostly tinkling of piano keys—an atmospheric story that adds a spooky touch to the night.

Chicago River: Gliding along the riverbank, you’ll learn about the 1915 maritime disaster that claimed 800 lives, a story that still echoes through the city’s memory.

Gangster Lore: The tour also takes you past sites linked to Chicago’s notorious gangsters, giving context to the city’s darker reputation in a fun, accessible way.

City Lights and Nighttime Views

Beyond the haunted tales, you’ll love the spectacular nighttime views of Chicago’s landmarks. The buildings lit up at night create a stunning backdrop, making the experience both eerie and beautiful. Several reviews mention how much they enjoyed seeing Chicago’s architectural highlights under the glow of evening lights—something we think adds a special touch to an already memorable tour.

The Group and Duration

The tour is deliberately kept small, with a maximum of 8 travelers, which promotes a fun, personalized atmosphere. As one reviewer said, “our guide Carrie was hilarious and made our tour truly memorable,” and many others praise their guides’ friendliness and knowledge.

The entire experience lasts about 2 hours, which is just right—long enough to see significant sites and hear their stories without feeling rushed or exhausted.

Cost and Value

At $75.48 per person, the tour is a solid value, considering the fun of riding a Segway, the stories shared, and the chance to see Chicago from a different perspective. It’s a good price for such a personalized experience, especially since the reviews repeatedly mention how guides go above and beyond to make everyone feel comfortable and keep the atmosphere lively.

Practical Considerations

You must be at least 12 years old and weigh between 100 and 260 pounds. The tour runs in all weather conditions, so dressing appropriately is wise—think layers and comfortable shoes. Since most reviews mention booking 11 days in advance on average, planning ahead is essential, especially during the busy summer months.

Review Highlights and Authentic Feedback

Travelers consistently praise the knowledgeable guides—with some mentioning guides like Jeremy, Kate, or Tammie as making the experience “fun,” “informative,” and “memorable.” Many reviews note the “great ghost stories,” “beautiful sights,” and the fact that riding the Segway is surprisingly easy after a brief practice.

A few reviewers also highlight the safety measures, such as helmets and attentive guides who communicate hazards clearly, which helps newcomers feel secure. One quote sums this up: “We felt very safe with her and she constantly communicated with us of hazards etc.!”

Potential Drawbacks

While most reviews are glowing, a handful mention weather-related issues or minor hiccups like reservation problems. For example, one reviewer noted that “Viator screwed up the reservation,” but the staff quickly rectified the issue. As the tour operates in all weather, dressing warmly in colder months or rain gear in wet weather ensures a comfortable experience.

Who Will Love This Tour?

This tour suits travelers who enjoy storytelling, light adventure, and nighttime cityscapes. It’s perfect for those interested in Chicago’s more macabre stories, from tragic fires to maritime disasters and gangster lore. The small group size and friendly guides make it an excellent choice for families, couples, or groups of friends seeking a fun, active way to learn about the city’s past.

It’s also a good fit if you’re new to Segways—many reviews describe the learning curve as gentle and accessible—making it friendly for first-timers. If you’re after a unique, lively experience that mixes history, humor, and a bit of spooky charm, this tour checks all those boxes.

The Sum Up

The Chicago Haunted Crime & The Outfit Segway Tour offers a lively, engaging way to explore the city in the evening. It combines authentic stories of tragedy and gangster tales with the fun of riding a Segway through illuminated streets. The personalized attention from guides and the spectacular night views make it stand out as a memorable, active experience.

While weather can influence the comfort level, the overall value and uniqueness of the stories make this tour a great pick for anyone interested in Chicago’s darker chapters, or simply looking for a fun night adventure with a friendly guide. It’s especially suited for those who enjoy lively storytelling and want to see the city from a fresh perspective—by night, on a Segway.

FAQ

Is this tour suitable for children?
Yes, the minimum age is 12 years old, making it accessible for older children and teenagers.

How long is the tour?
The tour lasts approximately 2 hours, giving enough time to see several sites and hear their stories without feeling rushed.

What should I wear?
Dress appropriately for the weather, as the tour operates in all conditions. Layers and comfortable shoes are recommended.

Are helmets provided?
Yes, helmets are included and fitted during the check-in process to ensure safety.

What if I am nervous about riding a Segway?
Most reviews indicate the training session is thorough and guides are very patient, making it easy for beginners to feel confident.

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

Is the tour accessible in bad weather?
Yes, it runs in all weather conditions, but you should dress appropriately for rain, cold, or wind.

What destinations are included?
Highlights include the alley where the Iroquois Theatre fire occurred, the Michigan Avenue hotel ballroom, and the Chicago River—plus spectacular city lights.

How many people are in each group?
Tours are limited to 8 travelers, promoting a friendly and personalized experience.

This tour offers a different, lively side of Chicago—perfect for those who love stories of the city’s darker past, enjoy active sightseeing, and want to experience the city illuminated at night. It’s a memorable way to combine fun, history, and a touch of mystery—all on a Segway.