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!

VIP Tandem Skydiving

  • Duration
    1 Hour
  • Availability
    Weekends Only
  • Gold Skydive $389 per Person

    $39 deposit
    Includes Videos AND Pictures

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!

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). YOU MAY NOT SKYDIVE IN BOOTS, HARD-SOLED SHOES, SANDALS, OR BAREFOOT.
  • Wear comfortable clothes for the day. You may jump in shorts (mid-thigh or longer suggested) and a t-shirt if you wish. We will provide everything else you need, including goggles (and a full-body jumpsuit and gloves/hat if necessary). At jump altitudes, temperatures are generally a bit cooler than on the ground, so if you chill easily, dress a bit 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.

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 during check-in and may have to complete their waiver onsite. A link for the online waiver will be sent upon completion of your booking, or you can follow this link: 2020 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 2019 waiver, you are good for all of 2019). We have the lowest package prices in Chicago, have the lowest deposits, and our 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. If you are under the maximum weight for your height according to our chart, and you weigh over 210lbs, there will be an extra charge (over 210-239lbs= $30, 240-270lbs=$50, 270-300lbs=$80. We can skydive safely with many people up to 300 pounds, but it is much more difficult for the instructor and creates more wear and possible damage to the skydiving equipment. If you weigh over 300lbs (on our scale, in your clothing), we cannot skydive with you under any circumstances.

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

  • Duration
    3 Hours
  • Availability
    Weekdays or Weekends

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.

  • Duration
    2 Hours or Less
  • Availability
    Weekdays Only

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.