The Chicago Insider Segway Tour offers a unique opportunity to explore the city’s renowned landmarks and hidden histories. Guided by knowledgeable locals, small groups glide through the vibrant streets, discovering iconic sites like Millennium Park and learning about Chicago’s captivating mafia past. With comprehensive training and safety equipment provided, this tour promises an engaging and immersive experience for visitors seeking to uncover the city’s diverse charms. The affordable pricing and convenient logistics make it an appealing choice for those eager to delve deeper into the Windy City’s rich tapestry.
Key Points

- Discover iconic landmarks and hidden gems of Chicago on an engaging small-group Segway tour with a knowledgeable local guide.
- Enjoy a personalized tour experience with a maximum of 5 participants, allowing for increased interaction and a tailored itinerary.
- Receive comprehensive Segway operation training and safety equipment, ensuring a safe and comfortable ride throughout the tour.
- Explore the city’s vibrant Lakefront, Millennium Park, and its fascinating mafia history during the 96% recommended tour.
- Benefit from clear meeting instructions, parking options, and a centralized departure point at Absolutely Chicago Segway Millennium Park/Grant Park office.
Tour Overview and Highlights
The Chicago Insider Segway Tour offers visitors an engaging and immersive experience to explore the city’s iconic landmarks and hidden gems.
This small-group tour allows travelers to navigate the bustling streets and lakefront on a Segway, accompanied by a knowledgeable local guide.
Highlights include discovering Millennium Park, the Lakefront, and learning about Chicago’s mafia history and innovations.
With a 96% traveler recommendation and a Badge of Excellence, this 76-dollar experience promises an enjoyable and informative way to uncover the city’s rich culture and history.
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Tour Experience and Structure

As part of the Chicago Insider Segway Tour, participants are first introduced to the city’s history and highlights before embarking on their Segway journey.
This personalized tour includes:
- A comprehensive training session to ensure participants feel comfortable and confident on the Segway
- Live narration by a professional local guide, providing in-depth information about Chicago’s landmarks and stories
- A small-group setting, with a maximum of 5 travelers, for a more intimate and tailored experience
- Helmet and storage bag provided for added safety and convenience
Meeting Point and Logistics

The meeting point for the Chicago Insider Segway Tour is located at 300 E Monroe St, Chicago, IL 60601, USA. This is the departure point from the Absolutely Chicago Segway Millennium Park/Grant Park office.
For parking, the tour company suggests using the Millennium Park Parking Garage, and they provide a $10 off voucher. The tour returns to the original meeting point at the end.
Participants must complete a waiver prior to arrival. The tour operates in all weather conditions, and ponchos are provided if it rains.
Participant Requirements and Safety

To participate in the Chicago Insider Segway Tour, there are certain requirements and safety considerations.
The tour has a minimum age requirement of 12 years, and children under 18 must be accompanied by a guardian. Participants must also fall within a weight range of 100-260 pounds.
Plus, the tour is not wheelchair accessible, and participants must be able to climb and descend stairs. Pregnant women or those with serious medical conditions are advised against joining the tour.
All participants must complete a waiver prior to arrival, and the tour operates in all weather conditions, with ponchos provided if it rains.
Exploring Millennium Park on Segway

Though the tour starts from the Absolutely Chicago Segway Millennium Park/Grant Park office, the real highlight of the Chicago Insider Segway Tour is the exploration of Millennium Park itself.
Gliding effortlessly on Segways, guests get an intimate experience of this iconic Chicago landmark. They marvel at the famous Cloud Gate sculpture, also known as "The Bean," and cruise along the park’s winding paths, taking in the lush landscaping and stunning architecture.
The Segway format allows for efficient navigation and a more immersive sightseeing experience compared to walking. This part of the tour showcases Chicago’s renowned public spaces and modern design.
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Discovering Chicago’s Lakefront

After exploring the vibrant Millennium Park, the Chicago Insider Segway Tour continues its journey along the picturesque lakefront. Guests are treated to stunning views of Lake Michigan and the city’s iconic skyline.
The tour highlights:
- Breathtaking panoramas of the expansive shoreline and beaches
- Iconic landmarks like the Navy Pier and Museum Campus
- Insights into the city’s maritime history and engineering feats
- Opportunities to stop and capture memorable photos along the way
The lakefront segment offers a serene contrast to the bustling city, providing a truly immersive experience of Chicago’s diverse landscapes.
Uncovering the City’s Mafia History

How deep does the rabbit hole of Chicago’s dark past go? On this segway tour, you’ll uncover the city’s notorious Mafia history. From the infamous Prohibition-era gangsters to the shadowy power brokers in City Hall, Chicago’s underworld plays a starring role. Take a look at some of the key figures that shaped this sordid side of the city:
| Notorious Mobsters | Infamous Criminal Acts | Legendary Hangouts | Corrupt Politicians |
|---|---|---|---|
| Al Capone | St. Valentine’s Day Massacre | The Green Mill | Richard J. Daley |
| Johnny Torrio | Murder Inc. Killings | The Lexington Hotel | William Hale Thompson |
| Frank Nitti | The Outfit’s Extortion Rackets | The Cotton Club | Edward Kelly |
| Sam Giancana | Assassination of Michael Cassius McDonald | The Bismarck Hotel | Anton Cermak |
Traveler Reviews and Ratings

The Chicago Insider Segway Tour has earned high praise from travelers, with a remarkable 96% recommendation rate based on 51 reviews.
Feedback from participants highlights several key aspects:
- Excellent guides who provide engaging and informative narration about the city’s history and highlights
- Enjoyable, fun-filled experience exploring Chicago’s iconic landmarks and neighborhoods on Segway
- Personalized, small-group format that allows for a more intimate and tailored tour
- Well-organized logistics, including clear meeting instructions and convenient parking options
With its high ratings and positive traveler reviews, the Chicago Insider Segway Tour offers an immersive and memorable way to discover the city.
Frequently Asked Questions
How Frequently Do the Tours Run?
The tour frequency is not explicitly stated in the provided information. However, the tour is described as a "small-group" experience, suggesting it likely runs multiple times per day to accommodate different groups of travelers.
Do the Tours Operate Year-Round?
The tours operate year-round, regardless of weather conditions. Ponchos are provided if it rains, allowing the tours to proceed in all seasons. The tour description indicates it runs consistently throughout the year.
Can the Segways Accommodate a Large Group Booking?
The Segway tours can accommodate bookings for larger groups, though the maximum group size is 5 travelers to maintain a personalized experience. Group discounts may be available for reserving multiple spots on the same tour.
Are There Any Student or Military Discounts Available?
The Chicago Insider Segway Tour does not appear to offer specific student or military discounts. However, the tour operates on a small-group basis, which may provide a more personalized and cost-effective experience for groups. Customers are advised to inquire about any available discounts when booking.
What Is the Closest Public Transportation to the Meeting Point?
The closest public transportation to the meeting point at 300 E Monroe St, Chicago, IL 60601 is the CTA (Chicago Transit Authority) bus and train system. The closest CTA station is the Adams/Wabash station, approximately 0.2 miles away.
The Sum Up
The Chicago Insider Segway Tour offers an engaging and immersive experience for visitors to explore the city’s iconic landmarks and hidden gems. With personalized interactions, comprehensive training, and safety equipment, guests can enjoy a memorable adventure on Segway while discovering the highlights of Chicago, including Millennium Park and the city’s intriguing mafia history. Priced at $76, this tour provides a convenient and informative way to experience the Windy City.
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