Chicago Insider Segway Tour

Exploring Chicago becomes easier and more fun with the Chicago Insider Segway Tour. Priced at $64.80 per person, this 2-hour and 20-minute guided experience offers an engaging way to see some of the city’s most famous landmarks. Starting near Millennium Park, the tour delivers a personalized introduction to Chicago’s history, architecture, and quirky stories—all on the zippy, easy-to-learn Segway.

Perfect for those who want a fast-paced, interactive tour, this experience is suitable for ages 12 and up. The tour operates rain or shine, with safety gear and a thorough training session included, ensuring everyone can enjoy riding confidently. Since the small group size caps at just five travelers, it promises an intimate and tailored experience, with an enthusiastic local guide leading the way.

Key Points

• Personalized small-group experience with a maximum of 5 travelers
• Includes comprehensive training and safety gear for beginners
• Cruises around Millennium Park and along Chicago’s Lakefront
• Learn surprising stories about Chicago’s mafia past and city innovations
• Operates in all weather conditions, with ponchos provided if needed
• Most bookings are made about 30 days in advance, so plan ahead

Meet Your Guide at Millennium Park for a Fun Start

The tour begins at 300 E Monroe St near Millennium Park. After a personalized training session, you’ll feel comfortable riding your Segway before heading out to explore. The guides are known for being funny, knowledgeable, and engaging, making the learning curve smooth for first-time riders.

This initial part of the tour emphasizes safety and ease of use. Helmets and a bag on the Segway for personal belongings are provided. Once trained, you’ll be ready to cruise confidently through Chicago’s lively streets, enjoying the freedom of two wheels.

Iconic Millennium Park and Nearby Landmarks

The first stop is Millennium Park, where you’ll glide past famous sights like the Cloud Gate sculpture and the Jay Pritzker Pavilion. Your guide offers insights into the park’s design and significance, making this iconic location come alive beyond photos.

From Millennium Park, the tour takes you through Chicago’s newest neighborhood, Lakeshore East. You’ll see the Chicago River’s mouth, and visit yacht clubs and harbors. The guide shares stories about Al Capone’s stomping grounds, adding a touch of Chicago’s colorful past to the sightseeing.

Rolling Along the Chicago Lakefront

The second stop along the route is the Lakefront, where you’ll enjoy a 20-minute ride along the Lakeshore. Here, you can pause to hear about Chicago’s maritime history and city development. This stretch provides great views of the lake, as well as opportunities to learn surprising facts about Chicago’s architecture, history, and local stories.

This part of the tour emphasizes scenic views and relaxed riding, perfect for photo opportunities and enjoying the breeze along the water.

Exploring Chicago’s Architectural and Historical Sites

Throughout the tour, the guide shares tales about Chicago’s mafia history and city innovations that shaped the town. These stories are woven into the route, making the sightseeing feel lively and informative. The tour offers a good balance of history, architecture, and fun facts, making it suitable for those interested in Chicago’s past and present.

The tour’s pacing allows for quick stops and smooth riding, ensuring you see more in less time without feeling rushed.

Safety and Accessibility Considerations

All riders must weigh between 100 and 260 pounds and be at least 12 years old. The tour is not suitable for pregnant women or those under the influence of drugs or alcohol. Riders should be capable of climbing and descending stairs independently and be comfortable standing for the duration.

The activity operates rain or shine; ponchos are provided in case of rain. Participants must complete a waiver beforehand; the process is quick and online, ensuring smooth check-in.

Booking and Cancellation Flexibility

Most bookings are made about 30 days in advance, reflecting high demand. The tour offers a free cancellation policy if canceled at least 24 hours before the scheduled time, giving flexibility in case plans change. Cancellations within 24 hours are non-refundable, so advance planning is recommended.

The small group size and personalized guide experience make this tour a popular choice for those who prefer an intimate Chicago adventure.

What Sets This Tour Apart from Others

Unlike larger bus or boat tours, the Chicago Insider Segway Tour delivers a personalized, interactive experience. The inclusion of comprehensive training and safety gear ensures first-timers feel comfortable. The small group size enhances engagement and allows the guide to tailor stories and insights.

This tour stands out for its combination of scenic lakeside riding, city landmarks, and local lore, all delivered in a fun, energetic manner by guides praised for their knowledge and humor.

Who Will Enjoy This Tour Most

This experience suits active travelers who enjoy learning on the go and prefer small group excursions. It’s ideal for those interested in Chicago’s architecture, history, and stories, and who want a more dynamic way to explore the city.

Perfect for first-time visitors and adventure seekers, the tour’s affordability and convenient location make it a compelling option for a memorable day in Chicago.

Frequently Asked Questions

Is this tour suitable for children?
Yes, children aged 12 and older can participate, provided they meet the weight requirements and can climb stairs independently.

Do I need prior experience with Segways?
No. The tour includes a full training and safety briefing so even beginners can ride confidently.

What should I wear?
Wear comfortable closed-toe shoes and dress appropriately for the weather, as the tour operates rain or shine.

Is the tour accessible for people with mobility issues?
Participants should be able to climb and descend stairs without assistance; the tour may not suit those with significant mobility challenges.

Can I cancel if my plans change?
Yes, full refunds are available if canceled at least 24 hours in advance. Cancellations made later are non-refundable.

How large is the tour group?
The maximum group size is 5 travelers, ensuring an intimate and personalized experience.

This Chicago Insider Segway Tour offers a lively, informative, and fun way to discover the city’s highlights on two wheels. With attentive guides, scenic stops, and a flexible booking policy, it appeals to those seeking an active and engaging Chicago adventure.