Chicago on Two Wheels (or rather, two Segways): A Review of the 2-Hour Guided Tour
If you’re thinking about adding a bit of adventure and a different perspective to your Chicago trip, a 2-hour guided Segway tour might just be the move. We haven’t done this specific tour ourselves (yet!), but from what travelers say and the tour’s detailed description, it offers a lively and engaging way to see some of the Windy City’s most famous sights.
Two things stand out immediately: First, the small-group setting caps at just eight people, which promises a more personalized experience. Second, the stunning views of iconic landmarks—like Millennium Park and Buckingham Fountain—are clearly a highlight. Though, as with any activity, there are a few caveats. The duration clocks in at around two hours, which is perfect for a quick yet comprehensive snapshot of the city, but some might find this a bit rushed if they want a deep dive into Chicago’s history.
This tour is well-suited for anyone looking for a fun, active way to explore without the exhaustion of walking all day. It’s ideal if you’re comfortable on a Segway (or willing to learn) and want an exciting, memorable experience that combines sightseeing with a little bit of thrill.
Key Points

- Efficient sightseeing: Cover a lot of ground in just two hours
- Intimate group size: Limited to 8 participants, making it more personal
- Expert-guided: Guides are knowledgeable, professional, and helpful
- Scenic stops: Focus on landmarks like Millennium Park, Buckingham Fountain, and Museum Campus
- Family-friendly?: While not specifically advertised for kids, the reviews suggest even older adults and those with special needs can enjoy it
- Weather-dependent: Confirmations are immediate, but poor weather may cause cancellations for which you’ll be refunded or rescheduled
The Experience: What You Can Expect

The tour kicks off at a convenient downtown Chicago location—2 E 8th St, easy to reach via public transportation. Once you meet your guide, you’ll spend some time getting comfortable on your Segway, with training and safety gear provided. The initial instructions are straightforward and designed to make everyone feel confident, even if you’ve never been on a Segway before.
From there, the fun begins. You’ll glide through Chicago’s scenic downtown, taking in Grant Park, home to the famous Buckingham Fountain, which is a sight to see, especially in good weather. The guide will share stories and insider facts about the landmarks, making the experience both fun and educational.
You’ll also explore around the Museum Campus, which offers fantastic views of Lake Michigan and the skyline. The tour includes riding near the lakefront, giving you a chance to see some of Chicago’s most photogenic spots. Some routes also feature a cruise along the Riverwalk, where you’ll pass Navy Pier and historic bridges, and cruise up Michigan Avenue, a shopper’s paradise.
While the main focus is on sightseeing, the reviews show that guides like Mike make the experience engaging with their stories and humor. One review mentions that the guide was professional, accommodating, and very knowledgeable. Another highlights that the instructions were clear, and riders of different ages felt comfortable on the Segway, even a grandmother with her grandson.
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The Landmarks and Stops

Let’s break down some of the stops that make this tour memorable:
Millennium Park and Cloud Gate (The Bean): Although not explicitly mentioned in the itinerary, these iconic sights are often part of city tours and are easy to access from the route. They provide perfect photo opportunities and are a highlight for first-time visitors.
Buckingham Fountain: As one of Chicago’s most famous fountains, it’s a grand centerpiece in Grant Park. The fountain’s size and beauty make it a natural stopping point where you can snap some photos and listen to the guide share fun facts.
Museum Campus: The expansive park area is home to several museums and offers spectacular lake views. The park’s open spaces are perfect for a smooth Segway glide and are often praised for their scenic beauty.
Chicago River and Bridges: If your route includes the Riverwalk, you’ll get scenic views of Navy Pier, Chicago’s historic bridges, and the bustling river traffic. This part of the tour often gets rave reviews for its picturesque qualities.
Michigan Avenue: Riding along this famous street allows you to see some of Chicago’s most popular shopping and architectural spots, giving a bit of a city buzz to your experience.
What the Reviews Say
The overwhelming majority of reviews are glowing, with a 5-star rating and a 94% recommendation rate. Many users mention that guides like Mike are “fantastic,” “professional,” and “knowledgeable,” making the experience not just about the sights but also about the stories and background told along the way.
One reviewer says, “We had a blast on the Segways! Mike was a great teacher and took us to some great places for some picture opportunities.” Others appreciate how accessible the activity is, with comments like “Even a grandmother and a child with special needs could learn the Segway,” reflecting that the activity is manageable for a wide range of ages and abilities.
However, not all feedback is perfect. A few users mentioned issues like the meeting point being hard to find or the storefront being cluttered and unkempt—not the best first impression. One person had a negative experience with a guide who spoke quickly and was hard to understand, which highlights the importance of choosing a reputable provider and possibly requesting a guide known for clear instructions.
A notable caution from a couple of reviews concerns weather—since the tour relies on good weather, cancellations due to rain or storms are possible, but the policy offers a full refund or rescheduling options.
Is It Worth the Price?
At $65 per person, this tour hits a good middle ground in terms of value. Considering the length (about two hours) and the inclusion of training, safety gear, and a knowledgeable guide, it’s a pretty fair deal for a fun, guided activity with lots of sightseeing.
Compare that to walking or biking, and you’ll see how much ground you cover in a shorter amount of time, with the added fun of riding a Segway. Plus, being part of a small group means you get more personalized attention and a relaxed atmosphere.
Practical Tips and Things to Keep in Mind

- Book in advance: The tour is usually booked about 18 days ahead, so plan ahead if you want to secure a spot during peak times.
- Weather considerations: Confirm the forecast before your tour day, as poor weather might lead to cancellations.
- Comfort on the Segway: Be prepared to spend some time learning how to ride; most people find it easy, but a quick warm-up helps.
- Group size: Limited to 8 travelers, so it’s intimate and less chaotic.
- Meeting point: Keep an eye out for the somewhat cluttered storefront—arrive a little early if possible.
- Tip your guide: While gratuity isn’t included, the reviews suggest guides like Mike make the experience memorable, and a tip is appreciated.
The Sum Up
This 2-hour guided Segway tour of Chicago offers a lively, engaging way to see some of the city’s best sights without the exhaustion of walking. The small group size and knowledgeable guides make it a friendly, approachable experience, suitable for those comfortable on a Segway or willing to give it a try.
Travelers who love fun activities that combine sightseeing with a dash of adventure will find this tour a worthwhile addition to their Chicago itinerary. It’s especially appealing if you want to maximize your sightseeing in a short period and enjoy some memorable moments along the lakefront and downtown.
While it may not cover every corner of Chicago, it hits many of the highlights with efficiency and flair—plus, the views and stories help bring the city’s character to life. Just keep an eye on the weather, book ahead, and prepare to have a great time gliding through the Windy City.
2-Hour Guided Segway Tour of Chicago
“If you want to explore the "museum campus" this is the tour for you, if you except a tour of the city then you will be disappointed. The descriptio…”
FAQ

Is this tour suitable for children?
While not specifically advertised as family-friendly, reviews indicate that even older adults and those with special needs have enjoyed it, suggesting it’s accessible for a broad age range.
How long does the tour last?
The tour runs approximately 2 hours, including training and safety gear, with most of that time spent riding and sightseeing.
Where does the tour start and end?
It begins at 2 E 8th St, Chicago, and ends back at the same location.
What is included in the price?
The price covers the guided Segway tour, including Segway training and safety gear.
Are there any additional costs?
Gratuity for guides and meals are not included.
What about weather cancellations?
The tour requires good weather; if canceled due to poor conditions, you’ll be offered a different date or a full refund.
How many people are in each group?
A maximum of 8 travelers per tour, making for a more personalized experience.
Is it easy to learn how to ride a Segway?
Most travelers find it straightforward, especially with guide instructions. Several reviews mention that even first-timers felt comfortable quickly.
Can I cancel if I change my mind?
Yes, cancellations are free if made at least 24 hours in advance; less notice means no refund.
If you’re after a memorable, active way to see Chicago’s highlights, this guided Segway tour could be just the ticket. It combines fun, scenery, and stories—making your visit a little more special.
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