Make sure to arrive 15 minutes before the START time on your reservation details.

Flex-Time™ Tandem Skydive

You pick the day, we'll assign the check-in time. Weekdays Only.

Flex-Time™ Tandem


Skydive Windy City Chicago


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.

Flex-Time™ discount agreement

I wish to let Skydive Windy City choose my appointment time on the day I have selected. I will be notified via email by 9pm the night before what time I am expected to arrive (between 9am and 6pm). I understand if I am late for my flex-time skydive, I may lose the flex discount.


The prices listed while booking will not include any discounts other than the Flex-Time™ discount.  All other applicable discounts (group, student, birthday, public servant) are applied during check-in on the day of your skydive.

What to Wear/ 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 your day. You may jump in shorts (mid-thigh or longer suggested) and a t-shirt if you wish. We provide everything else you need, including goggles (and a full-body jumpsuit and gloves/hat if necessary). At jump altitudes, temperatures are usually 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.

Down Payments

When making a reservation, we collect a $39 down payment per jumper*** to guarantee your spots.  Prices listed during booking will not include discounts you may receive at check-in. All discounts (group, flex-time, birthday, student, public servant) are applied when you arrive and pay the balance before the skydive.  All monies paid to Skydive Windy City can be refunded to you if you request to cancel and be refunded via email >24hrs prior to your appointment, or if weather (or circumstances outside our control) prevent your skydive and you choose not to reschedule.

***Customers will be charged a booking fee equal to 6% of total reservation price (usually about $15 for Bronze) for reservations not made in person.  This fee is charged by the booking system operator and we see none of it.  Booking Bronze skydives keeps the 6% fee at its minimum (remember you can select any package on arrival (only the Diamond package has limited availability).***

Bronze, Silver, Gold, or Platinum?

  • Bronze: no photos or videos included, they can be purchased online after skydive at normal prices
  • Silver: discounted package includes 60+ photos from skydive.
  • Gold: discounted package includes all Silver media plus 4-6 video clips from skydive in 1080p or better quality
  • Platinum: discounted package includes all Gold media plus professionally edited video
  • Diamond package:  Our flagship product and the only product that includes an outside (3rd person) videographer.  This product has limited availability.  Customer receives 60+ DSLR photos and 4k video taken by the outside videographer AND one complete 360º (VR) video taken by the tandem instructor (so you can use gestures on your device and "look around" in the video).  The Diamond package is not selectable online, if you wish to reserve a diamond package, email us your request as soon as practical after you make your reservation, minimum 2 days ahead is recommended.

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

  1. Note:  Photos of specific moments are not guaranteed.  Photos are normally of just before exit, exit, freefall, a few of parachute flight, and landing.
  2. Note:  Common Video clips are of boarding, takeoff, pre-exit equipment check/interview, exit/freefall/parachute opening, and some parachute flight and landing.  No specific clips are guaranteed but if we don't get the exit/freefall/parachute opening clip due to camera malfunction you will receive 100% refund of the video product (ie. if you chose Gold or Platinum and still got the photos, you would be refunded to Silver level).  If we miss takeoff, pre-exit, or parachute flight and landing you will be entitled to a partial refund of the video product.  The boarding clip is not guaranteed because it relies on customer participation.  It is very rare that clips are missed and outside of the boarding clip, missed video is historically due to camera malfunction (which cannot be resolved on the fly).


Maximum Weight for Height:

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 

Deposit/payment is refundable in case of the following:

1. If we cannot skydive due to weather or conditions out of our control.
Note: We never cancel based on forecast information, but if we feel weather may affect/prevent your skydiving appointment, we will let you know via email usually the evening prior and morning of your appointment.

2. You may cancel for any reason (you don't even need to tell us why), and as long as you provide us with at least 24 hours notice, you may elect to receive a full refund. Email is the best way to cancel or reschedule.
Reply to any email from us (or use and we will take care of everything, including sending you a new confirmation. Email is the only way to guarantee your refund for the 24 hour policy, as we have a time-stamp from when the email was sent and received.
You may reschedule by phone by calling 219.210.3338.

There is no extra charge for rescheduling, as long as you give us 24 hours notice. Less than 24 hours notice for cancellation/rescheduling may forfeit their deposit. Less than 12 hours notice for cancellation or rescheduling and you could be charged the full price for the jump (or have your voucher redeemed).

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 for clarification.

2 hours or less Weekdays