Chicago: Gangsters, Ghosts, and Haunted Hotels Segway Tour

Glide through the dark underbelly of Chicago on a chilling Segway adventure. Uncover the city’s haunted past as a knowledgeable guide leads you through iconic sites, sharing captivating tales of notorious gangsters and ghostly encounters. From the eerie Congress Hotel to the somber Eastland Disaster memorial, this two-hour tour promises an intimate experience filled with breathtaking views of the illuminated skyline and a taste of the Windy City’s shadowy history. Are you brave enough to confront Chicago’s ghosts and grisly past?

Good To Know

• Explore Chicago’s haunted history and notorious gangster past on a 2-hour Segway tour, visiting sites like the Congress Hotel and Death Alley.
• Learn about the Eastland Disaster of 1915 and hear tales of Al Capone’s bootlegging and mob activities during the tour.
• Enjoy breathtaking views of the Chicago River and skyline at night while gliding on a Segway through the city.
• Experience an intimate tour with a small group size of 8 participants, led by a live guide sharing captivating stories.
• Comply with strict participant restrictions, including weight limits and medical conditions, to ensure a safe and memorable Segway tour.

You can check if your dates are available here:

Tour Overview

The Chicago Segway Tour promises an adventure-filled journey through the Windy City’s haunted history.

For 2 hours, you will zip through the streets on Segways, visiting iconic sites like the Congress Hotel, Death Alley, and the Eastland Disaster memorial.

Along the way, a live tour guide will share thrilling tales of Al Capone’s yacht and the city’s most haunted hotel.

Gliding along the Chicago River and down Michigan Avenue, guests will marvel at the illuminated skyline.

This small-group tour, limited to 8 participants, offers an immersive and intimate experience for those seeking a glimpse into Chicago’s dark past.

With a safety-first approach, the tour is suitable for most, though certain restrictions apply.

Experience Highlights

Participants on this thrilling Chicago Segway Tour will visit haunting sites that have long captured the city’s imagination.

They’ll cruise past the eerie Congress Hotel, where guests have reported ghostly encounters, and cruise through Death Alley, the site of a devastating fire.

Riders will also visit the Eastland Disaster site, where over 800 people tragically perished in 1915.

Hear chilling tales of Al Capone’s yacht and the ghosts said to haunt the city’s most haunted hotel.

Along the way, enjoy breathtaking views of the Chicago skyline illuminated at night as you glide along the Chicago River and Michigan Avenue.

Booking Information

Booking this thrilling Chicago Segway Tour is simple and flexible. You can reserve your spot now and pay later, plus you can cancel up to 24 hours in advance for a full refund.

The meeting point is at the NE corner of Columbus Drive and Monroe Street, so be sure to arrive 15 minutes early for check-in. Late arrivals won’t be able to join, so plan accordingly.

The tour operator has some participant restrictions, so check if you meet the requirements before booking.

Once you’re all set, get ready for an engaging, adventurous, and unforgettable exploration of Chicago’s haunted history on your Segway.

Participant Restrictions

Not everyone is eligible to join the thrilling Chicago Segway Tour. The tour has strict weight and height limits – participants must weigh between 99 and 260 lbs.

Pregnant women and those with mobility issues or epilepsy are also prohibited from riding the Segways. Children under 12 aren’t allowed on the tour for safety reasons.

All participants must sign a waiver and wear appropriate footwear like sneakers. The tour operator takes no chances, ensuring everyone’s wellbeing on this ghostly and gangster-filled adventure through the Windy City.

With these restrictions in place, guests can look forward to an unforgettable, adrenaline-pumping Segway experience.

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Customer Reviews

Thrilling adventures await those who brave the Chicago Segway Tour, as evidenced by the overwhelmingly positive customer reviews. Scoring an impressive 4.3 out of 5 stars, guests rave about the tour’s exceptional value, safety, and organization.

Families and teenagers particularly enjoy the engaging experience, with one reviewer describing it as a "must-do" for anyone visiting the city. Cruising along the Chicago River and gazing at the illuminated skyline leaves a lasting impression, while the haunting tales of gangsters and ghosts captivate the imagination.

Whether seeking an adrenaline-fueled exploration or a unique glimpse into the city’s storied past, the Chicago Segway Tour delivers an unforgettable adventure.

Haunted Sites

Chilling tales and haunting legends come alive as the Chicago Segway Tour explores the city’s most notorious haunted sites.

Gliding through the eerie streets, guests will discover the haunted Congress Hotel, where ghostly apparitions and unexplained noises have been reported for decades.

They’ll also visit Death Alley, the site of the tragic Eastland Disaster that claimed hundreds of lives.

At Fort Dearborn, the tour guides recount the harrowing history of this once-besieged military outpost.

Throughout the journey, thrilling stories of Al Capone’s yacht and Chicago’s most haunted hotel captivate guests, creating an unforgettably spooky adventure.

Gangsters and Yachts

As the tour glides past the glittering skyline, guests can almost imagine the notorious gangster Al Capone lounging on his luxurious yacht, scheming his next move.

Tales of Capone’s exploits and the dark underbelly of Chicago’s past come to life as the Segway winds through the city streets. Guides recount stories of bootlegging, brothels, and bloody mob wars that once plagued this bustling metropolis.

Guests lean in, envisioning the gangsters, molls, and henchmen who once prowled these very alleyways, seeking to uncover the secrets hidden in the shadows.

The tour offers a thrilling glimpse into Chicago’s notorious history, bringing the city’s shadowy past into vivid focus.

Chicago’s Skyline at Night

As the Segway tour glides away from the shadowy tales of Chicago’s gangster past, the group is met with a breathtaking sight – the city’s skyline illuminated against the night sky.

Towering skyscrapers reach for the stars, their windows aglow with the pulse of the city. The iconic Sears Tower stands tall, its distinctive silhouette a beacon guiding the way.

Cruising along the Chicago River, the group takes in the magnificent architecture that lines its banks, each building a work of art in the night’s soft glow.

The experience is nothing short of awe-inspiring, a chance to see the city from a unique perspective and witness its beauty come alive under the veil of darkness.

Frequently Asked Questions

Can I Bring My Own Segway on the Tour?

No, you can’t bring your own Segway. This tour provides the Segways for participants, ensuring a safe and seamless experience. Bringing your own Segway wouldn’t be allowed, as the tour group needs to stay together and follow the guide’s instructions.

Are There Any Age Restrictions for the Tour?

There are age restrictions for this tour – it’s not suitable for children under 12. Adventurous teens and families will love zipping through the city on Segways, exploring haunted sites and learning about Chicago’s notorious gangsters.

Is the Tour Suitable for People With Disabilities?

The tour may not be suitable for individuals with mobility impairments. Participants must be able to board and operate a Segway safely. Those with epilepsy or significant weight restrictions also cannot join the spooky, illuminated nighttime adventure.

Can I Take Photos During the Tour?

Participants can capture the eerie atmosphere and historic sites with their cameras throughout the tour. The guides encourage photo-taking, inviting guests to immortalize the haunting tales and chilling experiences along the way.

Is There a Dress Code for the Tour?

There’s no official dress code, but participants should wear comfortable, weather-appropriate clothing and closed-toe shoes. Dressing the part – perhaps with a gangster-inspired look – can add to the immersive, adventurous experience on this haunting Segway tour through Chicago’s storied past.

The Sum Up

Glide through the dark past of Chicago on this thrilling Segway tour. Witness the city’s haunted history up close, from chilling ghost stories to the notorious tales of Al Capone. With a knowledgeable guide, explore the eerie Congress Hotel and the somber Eastland Disaster memorial, all while enjoying breathtaking views of the illuminated skyline. This intimate adventure promises a captivating journey into the city’s shadowy underworld.

You can check if your dates are available here: