VIP Tandem Skydive

VIP Tandem Skydive Chicago

Skydive Windy City Chicago

Skydive like a VIP with us, you choose the day you want to jump, and you can come in anytime you choose. Reserve yours today with Skydive Windy City Chicago!
Skydive like a VIP! You choose the day you want to jump and you can come in anytime you choose, you will be checked in, trained, and put on the next flight!
  • Gold Skydive $399 per Person

    Videos AND Pictures included

Enjoy a VIP Chicago Skydiving Experience

Skydive like a VIP! Choose the day you want to jump (weekends only), and you can come in anytime you choose (between 10 a.m. and 3 p.m.). We’ll check you in, get you trained, and put you on the next flight (no waiting).
You will also receive all pictures and videos (edited and raw footage may take up to 48 hours), and a special VIP shirt. VIP Fast Pass customers are usually onsite for less than one hour.
Come experience the thrill of Chicago’s closest skydive center, easily accessible via the South Shore Line and just one hour from downtown.
Book online today and skydive the Windy City!

What to Bring

  • Bring a government-issued picture ID (passport, driver’s license, military ID, or state ID); you may not be permitted to skydive without it.
  • Wear (or bring) lace-up sneakers (tennis or running shoes).
  • Wear comfortable clothes for the day (as if you’re going on a picnic). You may jump in shorts (mid-thigh or longer suggested) and a t-shirt if you wish. We will provide the harness and goggles .  At jump altitudes, temperatures are generally a bit colder than on the ground, so if you get cold easily, dress somewhat warmer than you normally would. You should wear clothes that you don’t mind getting dirty, as it is common to get grass stains on landing.

Discount and Pricing Notes

All Jumpers have to complete the digital waiver and respond to verification email at least 24 hours before their reservation time. Those who do not complete the waiver 24 hours in advance will be charged an extra $10 quick-check fee at check-in and may have to complete their waiver onsite.

A link for the waiver will be sent upon completion of your booking, or you can follow this link: 2022 Tandem Skydiving Waiver If you have completed a waiver this calendar year, you do not need to do it again (i.e. once you completed one 2021 waiver, you are good for all of 2021). We have the lowest jump package prices in Chicago, the lowest deposits, and deposits are refundable with minimum 24 hours cancellation or if weather prevents your skydive. We pride ourselves on efficient, friendly customer service, and keeping your on-site time as low as possible.

All jumpers (regardless of weight) must be under the maximum weight for their height according to our height/weight chart.

Your safety is always our primary concern, and ALL JUMPERS must be under 250lbs, and be under the maximum weight for their height according to our Maximum Weight for Height Chart. If you are under the maximum weight for your height and weigh between 210lbs and 250lbs, there is an extra charge of $40. We can skydive safely with some people over 250lbs, and if you want a personal assessment for exception to the 250lbs maximum weight, email us directly at [email protected].

The Chicago area provides a number of choices for skydiving, and no matter where you go, the skydive is going to be amazing. The difference is location/proximity to you. We have the best location for views of Chicagoland and are closest to the city of Chicago. We jump two miles from Lake Michigan and are only an hour drive from the Loop. On your flight up and skydive, you can see from St. Joseph, Michigan all the way to Gurnee, IL (the whole south end of Lake Michigan), including the beautiful Chicago skyline. There is not a more beautiful place to skydive in the entire Midwest! Wherever you choose to skydive, we know you will have a great time, but if you want the best experience, Skydive Windy City Chicago should be your choice! Altitudes are approximate and may be affected by meteorological conditions or air-traffic control limitations.

Related Skydives

If you’re looking for a real thrill, you can’t top the adrenaline rush you’ll get from tandem skydiving near Chicago! Feel the excitement as you jump into freefall and enjoy views of the city skyline.
Save an extra $30 per person (on top of group and other discounts) on Flex Tandem Skydives. Skydive Windy City is Chicago’s safest, closest, and most scenic skydiving center.