Chicago Insider Segway Tour

Experience a unique glide that takes you behind the scenes of the real 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!”

On your 2-hour Segway adventure you will cruise along our city streets as you discovering the iconic landmarks, top sites, and hear live narration from our entertaining tour guides. Treat yourself by gliding around Millennium Park, and through Chicago’s newest neighborhood Lakeshore East, visit the mouth of the Chicago River, explore our yacht clubs and harbors, ride on our first airport, look at the stomping grounds of Al Capone and more! Your guide will help you envision Chicago at the turn of the century while falling in love with the modern city you see today.

Segways are safe to use, easy to learn, and fun to ride! We provide a thorough training session from our certified guides before we begin your tour. Our Segway instructors will teach your group how to ride a Segway one guest at a time so that each rider is comfortable and confident on their machine. Your tour will begin from our Millennium Park/ Grant Park office located at 300 E Monroe St. We kindly request that you arrive 15 minutes before your tour is scheduled to depart.



  • 18% Gratuity 18.00%
  • 20% Gratuity 20.00%
  • 15% Gratuity 15.00%

Cancelation Policy

We glide rain or shine!  Ponchos are provided when it rains.  WE REQUIRE A MINIMUM OF 36 HOURS ADVANCE NOTICE, OF YOUR TOUR’S DEPARTURE TIME, FOR ALL CANCELLATIONS AND RESCHEDULING (unless canceled by ACST).  Any tour that is canceled less than 12 hours prior to scheduled departure time is non-refundable and non-transferable. Cancellations made within 24 hours are subject to a 75% cancellation fee. ALL CANCELLATIONS are subject to an 8% processing cancellation fee (unless canceled by ACGT). Any tour booked through our website ( can be modified by the customer.  All other cancellations must be made with a customer service representative over the phone. In the event of extreme, inclement weather, as predicted by the National Weather Forecast Service, rain checks or rescheduling options are available.  Tours must depart at their scheduled departure time.  Guests who do not arrive at least 15 minutes before the scheduled departure time will not be able to participate and forfeit their payment.  Those persons who are under the influence of drugs or alcohol are not permitted to participate and a refund will not be issued. All participants must be at least 12 years old, WEIGH MORE THAN 100 LBS and less than 260 LBS in accordance with manufacturer recommendations.  An adult must accompany anyone under the age of 18 years old. Participants must be able to stand for extended periods of time. All participants must be able to ascend a flight of stairs without assistance.  Those who are pregnant are prohibited from participating in this activity.  Any group of 8 or more that desires to glide together is considered a private tour and is subject to a private tour service charge and gratuity. Please refer to all FAQ's for further stipulations and recommendations.  In the event of park festivals, races, construction, concerts, and the like, tours will be adjusted for safety and quality.  We do require all participants sign waivers and release forms absolving ACGT, LLC, all employees of ACGT from any and all litigant and responsibility for any and all injury or damages as you glide at their own risk.  Those who refuse to completely fill and sign a release form will not be able to participate and will not be granted a refund.  We do provide training and practice at the beginning of every tour.

WithinCancellation Fee
120 Days8.0%
1 Day75.0%
12 Hours100.0%
Guided Tours