Flex Tandem Skydive

Flex Tandem Skydive Chicago

Skydive Windy City Chicago
Reserve your Flex Tandem Skydive with Skydive Windy City Chicago today, the Most Scenic Skydiving Center! Experience the thrill with us and enjoy your time!
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.
  • Bronze Skydive $199 or Less

    No Videos or Pictures

  • Silver Skydive $249 or Less

    Pictures included

  • Gold Skydive $279 or Less

    Videos AND Pictures included

  • Platinum Skydive $309 or Less

    Our best video and photo package!

Rates are per person, group rates as low as $129, low $39 deposit, We match prices!

Save Money When you Choose Flex-Time Tandem Skydiving Closest to Chicago

When you choose the flex-time option for $30 per person discount (can be combined with group and other discounts), you simply pick the day you want to jump (reservations close 24hrs prior) and we’ll contact you the night before your skydive to let you know which timeslot you’ve been assigned.
Flex-time jumpers allow us to operate more efficiently, and we pass the savings on to you! Come take a leap of faith at the closest skydive center to Chicago, just a one-hour drive from downtown, easily accessible via the South Shore Line.

Price Matching

We’re happy to match prices for any skydive sold in our market (within 70 miles of Chicago and/or 70 miles of Michigan City, IN). Have questions? Just email us at [email protected] for clarification.

Deposits/Down Payments

We let you make a low $39 deposit to reserve your skydive. All discounts (flex-time, group, student, birthday, public servant) are applied when you arrive and pay your remaining balance before skydiving.

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

The Platinum skydive includes everything in the Silver & Gold packages plus professionally edited video and specialty photos.

Our Gold skydive package is the complete skydive with videos AND photos included at significant discount.

Our Silver skydive package is also the complete skydive, but with videos OR photos (jumper chooses at check-in).

The Bronze skydive is primarily for those who have jumped before. It is the complete skydive, but no videos or photos.

Groups may mix-and-match any of these packages and still qualify for the group discount

Flex-Time Weekday Skydive (you pick the day, we notify you of time the night before): $30 off per person. You may add one of the following (we’ll apply the best discount you qualify for): Birthday: $20 off if jumping on actual birthday, $10 off if within 14 days of birthday. Military: $20 off if active or retired, $10 off if veteran. Student: $10 off. Public Servant (Police, Fire, Educator): $10 off. Group discounts can be combined with any of these discounts. For groups of 2-3, each jumper will get $10 off, groups of 4-7 each get $20 off, groups 8-14 each get $30 off, and groups of 15 or more jumpers enjoy a $40 discount each. If your group is over 20, contact us for a quote. Groups do not need to choose the same package (i.e. a group of 3 can be 1 Bronze, 1 Silver, and 1 Gold and still get the group discount).

Add pictures or videos (choose at check-in) to bronze or voucher skydive for $68. Add videos and pictures to bronze or voucher skydive for $98 ($88ea if 2+ in group get both). Optional video editing: $10. Optional USB drive: $15 (standard is email link within 24 hours).

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.

We may offer limited time-frame discount skydiving vouchers through a third-party such as Groupon. You are free to purchase these vouchers when available, but note the fine print. They are limited in time-frame and package type. If you purchase a voucher you must book online following instructions provided after purchase. No extra discounts apply to voucher skydives (no birthday, group, weekday, etc…). You may add video and/or pictures at the prices noted above. We match any prices including our own, so if you wish for fewer problems and limitations, purchase directly through our website.

Skydive Windy City Chicago will match published prices of other skydiving centers in our market area (within 70 miles of downtown Chicago). Skydive Windy City Chicago also matches Groupon prices for offers from us and other centers in our market, just make the booking online as normal and let us know when you arrive with evidence of the price that we can verify.

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.
Go skydiving like a VIP! You choose the day you want to jump and you can come in anytime you would like. VIP Tandem Jumpers will be checked in, trained, and put on the next flight!