If you’re looking for a fun, fast, and informative way to get a feel for Chicago’s highlights, the Chicago Insider Segway Tour might just be your perfect match. This tour promises a zippy spin around some of the city’s most iconic sights, all while learning intriguing stories from passionate guides. While I haven’t tried it myself, I’ve gathered enough feedback and details to give you a clear picture of what to expect.
What I really like about this experience is how it combines personalized training with a relaxed, small-group vibe—only up to five people at a time. Plus, exploring on a Segway allows you to cover more ground than walking, making it seem like a brisk, manageable adventure rather than a tour that drags on. On the flip side, it’s not suitable for everyone; you need to meet certain weight and age requirements, and it operates rain or shine, so be prepared for weather.
This tour is great if you’re someone who enjoys active sightseeing but prefers to skip the walking marathon. It’s especially suited for travelers eager to see key Chicago sights without spending hours on foot. If you’re into learning quirky facts—like mafia stories or city innovations—this could become a highlight of your trip.
Key Points

- Small-group experience ensures personalized attention and easier navigation.
- Comprehensive training makes even first-timers feel confident on the Segway.
- Fast-paced exploration covers Millennium Park, Lakeshore, and other landmarks in just over two hours.
- Interesting narration offers stories beyond standard sightseeing.
- Weather readiness is essential—rain or shine, the tour runs.
- Age and weight restrictions are in place, so check your eligibility before booking.
Why This Tour Stands Out

When considering a city tour, especially one involving Segways, the feeling of safety and ease is key. This tour from Absolutely Chicago Segway Tours gets high marks for its clear, thorough training—crucial for first-timers or nervous riders. Many reviews highlight guides like Clark and Jeremy who are not just knowledgeable but also engaging, making the experience relaxed and fun.
Price-wise, at around $64.80 per person, you get a solid two hours of guided exploration. That’s reasonable considering the private or small-group setting, the inclusion of safety gear, and the live narration. Plus, most bookings happen about a month in advance, so planning ahead is smart.
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The Itinerary Breakdown

Stop 1: Millennium Park
Starting near Millennium Park, you’ll get to glide around with a tour guide sharing stories that bring the city’s history to life. The park is an obvious highlight—an instantly recognizable symbol of Chicago with its iconic Cloud Gate sculpture, also known as “The Bean.” From there, your guide will take you through the latest neighborhood, Lakeshore East, along with the Chicago River’s mouth, and some of the city’s yacht clubs and harbors.
What makes this stop particularly enjoyable is how the guide helps you visualize Chicago at the turn of the last century. One reviewer even pointed out, “Clark was a great teacher! Our first time on Segways and he was a great teacher,” highlighting how comfortable and approachable the training is.
Stop 2: Chicago Lakefront
Next, the tour rolls along the scenic Lakefront. You’ll get a chance to stop and listen to stories that aren’t common knowledge—about Chicago’s hidden gems and anecdotes that make the city unique. This part of the tour takes about 20 minutes, but it’s enough time to appreciate the stunning views of Lake Michigan and the city skyline.
Many visitors mention how riding along the Lakefront makes for a memorable experience—far more engaging than just walking along the shore. As one reviewer put it, “Had a really fun time with Jeremy,” and the upbeat narration made the entire experience more enjoyable.
What Makes This Tour Worth considering
The live narration and professional guides really elevate the experience. They do a good job blending city facts with entertaining stories, making the tour both educational and fun. Plus, the included helmet and personal bag are practical touches that show they’re thinking about your comfort and safety.
Adjustments for weather are straightforward—if it rains, ponchos are provided, so you won’t need to cancel just because of a drizzle. But be mindful that you must wear comfortable closed-toed shoes and dress according to the weather.
Who Should Book This Tour?

If you’re comfortable standing and can climb stairs without assistance, you’ll likely enjoy the tour without issues. It’s not recommended for pregnant women or those under the influence of drugs or alcohol. It’s also designed for ages 12 and up, with a weight range of 100 to 260 pounds.
This is a fantastic option for solo travelers, couples, or small groups wanting a lively, quick overview of Chicago’s highlights, with a dash of fascinating stories. If you want a leisurely walk, this isn’t it, but if you’re after speed, fun, and great narration, this is a winner.
The Practical Details

- Duration: About 2 hours 20 minutes, including training and riding.
- Cost: $64.80 per person—good value considering the personalized experience.
- Group size: Max five riders, which keeps things intimate and manageable.
- Booking: Most folks book roughly 30 days in advance, so plan early.
- Meeting Point: Near Millennium Park at 300 E Monroe St.
- Weather: Operates rain or shine; ponchos are provided.
- Age & Weight: Minimum age 12, weight 100-260 pounds.
- What’s Included: Live narration, safety gear, and a professional guide.
- What’s not included: Gratuities, food, and drinks.
Authentic Feedback from Participants

People seem to really enjoy this experience. One reviewer, Susan, said, “Clark was a great tour guide! Our first time on Segways and he was a great teacher. He was funny and knowledgeable.” That kind of personal touch makes a difference, especially for first-timers or nervous riders.
Another reviewer, Jennifer, called it the “highlight of the trip,” noting how much they saw and how upbeat the guide was. Many mention that the tour covers key sites efficiently without feeling rushed, which makes it perfect for those with limited time.
Final Thoughts: Is It Worth It?

If you’re after a fun, quick way to see Chicago, this Segway tour is a solid choice. It’s especially suited for travelers who appreciate stories and interesting tidbits about a city’s past and present. The guides’ knowledge and engaging manner shine through in reviews, making it more than just a sightseeing trip.
While it’s not the cheapest option, the small-group size, the interactive nature, and the chance to cover a lot of ground in a short time make it a good value. Remember to check your eligibility regarding age and weight, and be prepared for weather conditions—rain or shine, the tour runs.
All in all, this tour can be a memorable part of your Chicago trip, especially if you love active adventures and learning quirky city tales along the way.
Chicago Insider Segway Tour
“Clark was a great tour guide! Our first time on Segways and he was a great teacher. He was funny and knowledgeable”
FAQ

Q: How long is the Chicago Insider Segway Tour?
A: The total experience lasts about 2 hours and 20 minutes, which includes training, riding, and narration.
Q: What is the cost per person?
A: It’s approximately $64.80, offering a well-rounded guided experience with safety gear and narration included.
Q: Do I need prior experience to ride a Segway?
A: No, the tour includes a thorough training session, so beginners can feel confident after a quick orientation.
Q: Can kids participate?
A: Yes, the minimum age is 12 years old, and riders must meet weight requirements (at least 100 pounds).
Q: Is the tour suitable in bad weather?
A: Yes, the tour operates rain or shine, and ponchos are provided if needed.
Q: Where do I meet the guide?
A: The meeting point is at 300 E Monroe St, near Millennium Park.
Q: Are there any restrictions I should know?
A: You need to be able to climb stairs, wear comfortable closed-toed shoes, and not be pregnant or under the influence of alcohol or drugs.
Q: Can I cancel if I change my mind?
A: Yes, free cancellation is available up to 24 hours before the tour, with a full refund.
If you’re craving a lively, story-rich way to see Chicago on a compact schedule, this Segway tour ticks many boxes. Just remember to book early, dress appropriately, and prepare for a fun, zippy adventure through one of America’s most vibrant cities.
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