Chicago Insider 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.