Chicago Insider Segway Tour: Unveiling Forgotten History
4.9
51 Ratings
Chicago
Uncover the forgotten history of Chicago on a unique Segway tour. Explore the city's dark secrets, political scandals, and hidden stories in just two hours!
Duration: 2 hours, 20 minutes
Cancellation: 1 day learn more
Highlights
  • Millennium Park - 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. We kindly request that you arrive 15 minutes before your tour is scheduled to depart.

  • Chicago River - Stop by the mouth of the Chicago River, and hear strange but true stories of Chicago.
  • Chicago Lakefront - Ride your Segway along the Lakefront. Stop and hear unique stories about Chicago.
What's Included
  • Professional local guide
  • Live narration during the tour
  • Comprehensive training and orientation session
  • Helmet provided for safety
  • Bag on Segway for personal item storage
What's Not Included
  • Gratuities
  • Food and Drinks
Additional Information

Embark on an unparalleled tour experience with our latest Segway journey that covers diverse tales of Chicago, spanning from intriguing to bizarre. We’ll transport you backwards in time as you explore the metropolis from the perspective of the Chicago Syndicate, picking up murmurs of power from the city’s political upper crust while enjoying rarely heard narratives. You’ll find yourself astounded, thinking, ‘I would never have imagined!’ Cruise around Millennium Park, Lakeshore East’s burgeoning locale, and the picturesque lakefront as we reveal the untold history of Chicago within a span of two hours. The tales of the Chicago Mob, the real backstory of the 1968 Democratic National Convention, groundbreaking strides that altered history and much more will captivate your imagination!

  • Minimum age is 12 years old
  • Children under the age of 18 must be accompanied by a guardian
  • All riders must weigh a minimum of 100 pounds and not more then 260 pounds
  • We operate rain or shine, ponchos will be provided if it rains
  • Guests must complete our waiver before arrival. Please use this link- https://waiver.smartwaiver.com/w/jnbll3fksztkfzutdmzhn8/web/
  • Operates in all weather conditions, please dress appropriately and wear comfortable closed toed shoes
  • All riders must be able to climb and descend stairs without assistance
  • This activity is not appropriate for pregnant women
  • Those under the influence of drugs and alcohol will not be allowed to participate, and will not be given a refund
  • All riders must be able to stand for the duration of their tour
Location
300 E Monroe St
East Monroe Street
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.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(51 Ratings)
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L
Oct 29, 2022
Fun! - 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).
Review provided by Tripadvisor
Tracy
Jul 28, 2022
Would do again - 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.
Review provided by Tripadvisor
Marco
Oct 13, 2021
Amazing Segway Tour Experience! - 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!
Review provided by Tripadvisor
Ababaian
Oct 13, 2021
Great tour! - 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!
Review provided by Tripadvisor
J3145lclaurah
Sep 28, 2021
Great Way to See the City! - 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!
Review provided by Tripadvisor
Andreahrn27
Sep 28, 2021
Chicago insider tour - 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 ) !
Review provided by Tripadvisor
Lisaab45hp
Sep 27, 2021
Awesome Segway Tour - 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!!
Review provided by Tripadvisor
Brittanyst3438tv
Sep 27, 2021
Great way to see the lakefront and city - I have always enjoyed Segway tours but in Chicago particularly it is a great way to see the lakefront and the area around Grant park. I loved learning about some of the architecture and history of Chicago. Jeremy was a knowledgeable and fun tour guide. Segways are very easy to maneuver and is so much fun to ride on. I highly recommend going on this tour for a great time and an easy way to see and learn about the city.
Review provided by Tripadvisor
Sandrat1447
Sep 14, 2021
Great - Absolutely recommended! Fred, our guide was really funny and nice. We loved the experience. A must do in Chicago.
Review provided by Tripadvisor
Ringo4433
May 30, 2023
Try another Segway company first - 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.
Review provided by Tripadvisor
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