Prices checked on Sep 11, 2026Things to do in Chicago
This is a tour like no other! Our newest Segway adventure is completely unique and will cover the good, the bad, the ugly and the totally weird stories of Chicago. We will travel back through the ages as you discover the city through the lens of the Chicago Syndicate, hear the whispers of the city’s elite (or politicians), and be entertained by stories that are rarely told. You’ll think “No, really I never would have known!” Glide around Millennium Park, through the new neighborhood of Lakeshore East, and along the Lakefront as we unveil Chicago’s forgotten past in two hours! Your imagination will come alive as you hear stories of the Chicago Mob, the truth behind the 1968 Democratic National Convention, innovations that changed history, and so much more!
Take a look at some of the main attractions in Millennium Park, included Crown Fountains, Cloud Gate, and more!
You'll hear about this remarkable building while on tour.
You'll see and learn about this 2020 addition to our Skyline
We'll stop and here some fantastic stories along our River
Learn about the history of Navy Pier.
Chicago Insider Segway Tour lasts about 2 hours. The itinerary has 5 stops.
Prices start at $65 per person for this Chicago experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
The meeting point is Tours depart from Absolutely Chicago Segway Millennium Park/ Grant Park office located under the NE corner of Monroe Street and Columbus Drive near Millennium Park (level 2.) We suggest parking in the Millennium Park Parking Garage. We offer a $10 off voucher for anyone parking in the garage (subject to rules of MPG.) Once past the entrance gates, turn left toward Monroe Street. Proceed down to level 2. Park near 2W and follow the signs through the breezeway to our Lakeside office.. Hotel pickup is not part of this experience.
The experience is available in EN.
It is a small-group experience with a maximum of 5 participants.
Children under the age of 18 must be accompanied by a guardian
Yes, bookings are confirmed instantly.
By far my favorite part of our trip! Kevin our guide was TOP NOTCH! He was enthusiastic, knowledgeable, and a great guide! We saw many things and learned many insider things we would not have heard otherwise. Beautiful ride by the lake etc. Highly recommend. Worth every penny!
Hubby and I had a blast on the tour! Our guide was Marshall and there a quick training and practice and then we were off! Marshall was so funny and knowledgeable! We had such a great time and no matter how many times we come to Chicago and do tours like we ALWAYS learn something new and interesting! He recommended a couple of great hidden gems to see and I am so glad we did! Highly recommend this tour and this segway company!!
Thank you for joining us on the Chicago Insider Tour! It’s great to hear that you and your husband had such a fun time exploring the city with Marshall. He brings great energy and humor to each tour, and we’re thrilled you enjoyed both the stories and the ride. We hope to see you again for another adventure!
The tour itself was great. Beautiful sights of the city. However, it is difficult to find the office where the tour begins, it's dirty, the bathrooms were disgusting and almost out of toilet paper in all stalls ( and we were early morning arrival), the vending machines where you could buy water, pop, etc. Were empty. Save for a few sugar pops ( I had accidentally left my water in the taxi...that also got lost trying to find its way there). The Segways were old, beat up, broken down, wheels were wobbly and my husband was injured on both legs and pulled groin due to his faulty segway that finally the tour operator switched with hers and admitted it was a problematic tire. We have done this tour twice in years past and were disappointed. They need to do some upgrade ls and cleaning.
This is a great, women-owned company, with very fun tour guides. It’s easy to learn to ride a Segway quickly, and they give you instructions/practice before you head out. This insider tour goes on more city streets; the lakefront tour is prettier (note that Buckingham fountain is only on late May to early October).
Sarah our tour guide was wonderful at both trainings us and the history stuff was both fun and educational. The river side and water front were great.
We took the Insider Tour and Annie was our tour guide. She was very passionate and informative. We truly enjoyed ourselves and we learned a lot about Chicago. I highly recommend it to anyone who wants a memorable outdoor experience!
Annie was a delightful fountain of knowledge and a pleasure to spend two hours with! I learned so much about Chicago and she was able to answer every question even about things that weren't on the tour!
Went on the 9a Chicago Insider tour with a group of 5. Jeremy was our guide and was awesome! This is the third segway tour I've taken and it was my favorite!
We did the Chicago Insider Tour this past Sunday with Cedar and had an excellent time ! She was very informative and fun! She made sure the whole group was comfortable riding the Segway before we starred our tour. I would definitely recommend this tour to all our friends and fam who are visiting ( and even the ones living here like us ) !
Matt provided everything a first timer needed to enjoy a fun safe segway tour of the city. The entire experience from beginning to end was fabulous! Clark was exceptional in personally assisting me & my group in registering. I highly recommend!!
| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Chicago Insider Segway Tour | 2 hours | 4.9 (52) | $65 | |
 Chicago Architecture Center River Cruise aboard First Lady | 1h 30min | 4.9 (7,027) | $57 | View |
 Chicago Architecture River Cruise | 1h–1h 30min | 4.8 (16,969) | $39 | View |
 Chicago River 90-Minute Architecture Tour | 1h 30min | 4.7 (10,918) | $45 | View |
 Chicago Sightseeing River and Lake Cruise | 1h 30min | 4.7 (722) | $46 | View |
 Chicago River 45-Minute Architecture Tour from Magnificent Mile | 45 min | 4.7 (3,577) | $28 | View |
 Chicago By Night River and Lake Cruise | 1h 30min | 4.5 (432) | $50 | View |