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 may be charged up to 6% fees/taxes when booking.  This is calculated on the total reservation cost, not just the deposit value. 


Bronze, Silver, Gold, or Platinum?

  • The Platinum skydive includes all Gold level content plus professionally edited video and 2 customized photos
  • Our Gold skydive includes 15 hand-picked photos and a compiled (all clips in one file) 360º video.
  • Our Silver skydive includes 15 hand-picked photos.
  • 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

Maximum Weight for Height:

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.

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 info@skydivewindycitychicago.com) 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 (24 hours per day). The phones are manned by a local answering service, and they are trained to help for standard/common inquiries & tasks. 

Email only gets answered by actual skydivers who can answer any question/concern you may have.

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 info@skydivewindycitychicago.com for clarification.

2 hours or less Weekdays