Chicago Insider Segway Tour
Overview
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!
What's Included
- Live narration
- Thorough training and orientation session
- Helmet, and a bag on your Segway to store personal belongings
- Professional local guide
- Gratuities
- Food and Drinks
Meeting Location
300 East Monroe Street
Chicago, IL 60601, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
This activity ends back at the meeting point.
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
Millenium Park (pass by)
The St. Regis Chicago (pass by)
Additional Info
- Confirmation is instant and will be received at time of booking
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- 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
- This tour/activity will have a maximum of 5 travelers
Frequently Asked Questions (8)
Q: What is the cancellation policy for the Chicago Insider Segway Tour?
Cancellation Policy
Still have questions?
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Activity code: C-5254P11
Traveler Photos
Reviews
Average 4.90 out of 5 stars based on 52 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (8)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CST).
- Live narration.
- Thorough training and orientation session.
- Helmet, and a bag on your Segway to store personal belongings.
- Professional local guide.
- Gratuities.
- Food and Drinks.
This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Apr 2025The minimum age to participate is 12. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Chicago Insider Segway Tour is as follows:
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago Insider Segway Tour will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Live narration
- Thorough training and orientation session
- Helmet, and a bag on your Segway to store personal belongings
- Professional local guide
- Gratuities
- Food and Drinks
Additional Info
- Confirmation is instant and will be received at time of booking
- Not recommended for travelers with poor cardiovascular health
- Suitable for all physical fitness levels
- 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
- This tour/activity will have a maximum of 5 travelers
