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Chicago Segway Tours: A wild ride in the Windy City

Chicago Segway Tours: A wild ride in the Windy City

Last Updated on April 19, 2021

Every single day we are asked where we are from: fellow travelers, bus drivers, restaurant servers. Without hesitation, Dani replies simply, “Germany.” When I say the United States, however, people want me to be more specific. And so, I answer that I am from Chicago.

But the truth is, I am not from Chicago.

the bean chicagoI am from just outside of the city in one of the many northwest suburbs – from Chicagoland, as we call it. I am from just far enough away to be constantly enamored by this city. In the last two years, we have seen dozens of global cities, hundreds of dusty villages, and everything in between. While I have been home to visit Chicago many times since leaving the U.S. in 2001, on this past visit we were looking at Chicago through the eyes of experienced nomads. From the tops of Chicago’s towers and the tables of some of the city’s trendy and comfort-food-focused restaurants, we had a blast for the four weeks we spent in the city.

However, it was, quite surprisingly, our awesome Segway tour that truly allowed us to see Chicago from its most glamorous angles.

segway tour chicago millennium park
So how did we end up on a Chicago Segway tour?

One advantage of being a tourist in your own town is the chance to get personal recommendations from people you actually know and trust, and we didn’t think twice about trying out the frozen yogurt place, the secluded beach, the coffee shop around the corner. My step-dad, a Chi-town local and avid adventure traveler, kept recommending a Chicago Segway tour. It was hard to see ourselves on we considered a clunky machine that put sightseeing in reach for people who are too lazy/overweight/old to walk? Look, it’s not like we are entirely adverse to jumping on tourist bandwagons. After all, we went on a Mediterranean cruise and did a GoCar tour in Lisbon. But us? On Segways?
chicago segway toursIn the end, his soft but persuasive methods won and we were looking up tour companies, choosing City Segway Tours. Although we were initially nervous about our ability to block out judgmental stares about how silly we looked, after our fifteen minute confidence-building training session, we were pumped and ready to ride! Our guide, a native Chicagoan and all of 22 years old, shared loads of interesting Chicago history along the way, as well as keeping us at the right speeds throughout the ride.
chicago lakeshoreAs we quickly learned, the tour is as much about the Segway as it is the city. The machine, a scientific marvel, is a self-balancing, personal transportation device controlled entirely through minuscule motions of the feet; slight leans forward and backward affect the speed, while minimal usage of the ‘handlebars’ allowed us to float along, whiz around, turn on a dime in perfect 360 degree circles.

chicago segway tourThe Segway is not all fun and games, however. Riders have to keep their attention on the machine at all times, as just one momentary attention lapse can mean losing balance and falling off. The injuries could be pretty severe, but that is why our speed is limited to 5mph for the first half of the tour. After an hour, we feel like pros, and our guide bumps up our available speed to 8-9mph – and trust me, that is just as fast as we needed.
chicago wrigley buildingUsing the machine was a blast, but it is the tour aspect of the trip that won us over (and only afterwards, when reviewing the experience on TripAdvisor, we saw that 97% of hundreds of TripAdvisor reviewers all agree that the Chicago City Segway tour is the absolute best way to see the city!)

The tour started started at the City Segway Office, just north of the famous Millennium Park, where we watched an intense safety video that scared the pants off of us (in the name of safety), and outside where we learned to ride. We continued through Grant Park to Buckingham Fountain (which you may recognize from this little TV show) and then over to the Lake Shore, which hugs the coast of Lake Michigan for miles and miles in either direction.
chicago segway tours
Next it was on to Soldier Field (home of Da Bears) and over to Museum Campus – home Chicago’s impressive Field Museum, Shedd Aquarium and the Adler Planetarium. I’ve always said that if someone blindfolded you and set you down facing the waters of Lake Michigan, you would have no way of knowing that this massive body of water was not an ocean. With the impressive lake on one side and the city’s breathtaking skyline on the other, this leg of the tour was one of total enjoyment, pure awe, utter respect, and for this (kind of) Chicago native – swelling pride. It was here, in the back of the Planetarium, where we discovered the most picturesque views of the Chicago skyline I have ever seen. Now ain’t that somethin’?
chicago segway tourWith a bit of a buzz, we returned our sleek self-balancing ships back to the office, and noticed all the tours the company runs around the world. We could have already ‘Segwayed’ in Paris, Munich, New Orleans, Washington, DC, San Francisco, Atlanta, Berlin…but we have already been to those places. There is still Vienna and Budapest! Not all cities might work as great as Chicago did for these kinds of tours, but we would definitely do this again.
chicago skyline with willis tower

Tips for your Chicago Segway Tour:

1. Wear good shoes – you are essentially standing in one place for two-three hours (there are a few breaks, of course) so you will want supportive shoes, like gym shoes/trainers.
2. Dress appropriately – riding along the lake front means a strong breeze, but if you do the 10am tour, like we did, the sun will be beating down as well. Night tours will get chilly even in summer, thanks to that good ol’ Chicago ‘lake effect’.  Bring a jacket, wear shades and don’t forget sunscreen. Even in the winter, your nose will burn a bit on a sunny day without it.
3. The Segway has a pouch for 1-2 bottles of water, an iPad and a small camcorder, so it’s tech ready. The office has water bottles for $1.


chicago view from river



Monday 26th of March 2012

I half thought about trying to convince my family to try one of these the last time I was in Chicago. But we opted for an architecture boat tour instead. This sounds like SO much fun, though!


Tuesday 27th of March 2012

Amanda, I agree, the architecture boat tour is much fun, too! I think you would've enjoyed the Segway tour though and you should definitely go on one next time you're in Chicago :)

R.J. Archer

Sunday 25th of March 2012

I grew up in the south suburbs but that was LONG before the Segway was invented. Thanks to your article, my wife and I have just added this tour to our "must do" list for this summer's planned visit to Chicagoland!


Sunday 25th of March 2012

Aw, that's awesome R.J. Please let us know if you like it! If you guys are headed in July to the Taste of Chicago, we just might see you there! :-)

Scott - Quirky Travel Guy

Sunday 25th of March 2012

This is a timely post, as I'm preparing for a big series of Chicago articles on my blog next month. I've never done the segway thing but I should consider it. I'd like an opportunity to ride a segway even more than seeing the city!


Sunday 25th of March 2012

You should definitely give it a try if you can, and we'd also recommend the architecture boat cruise for amazing perspective on the city (post to come! :-) )

For 91 Days Travel Blog

Sunday 25th of March 2012

Too bad the fountain wasn't on.

We love Chicago and can totally see spending 91 days there. We visited couple of times and we must say it's one of our most favorite cities in the US!

Looks like you had a great day .. and that weather!!!


Sunday 25th of March 2012

Yes yes yes! Do 91 days in Chicago - but we have to be there when you do it!! That is so awesome that you love 'my city' so much, but seeing as how we are all brothers from other mothers, it's not a surprise it's one of your favs.

Brock - Backpack With Brock

Friday 23rd of March 2012

Getting to know your own (or close to your own) city as a tourist is always fun and enlightening! Looks like your Segway tour was awesome


Saturday 24th of March 2012

It really is! We also went on an architecture boat tour with several Chicago natives and everybody learned something new about their hometown :) And I am pretty sure that this wasn't our last Segway tour - so much fun!