Skydive Windy City Chicago

Chicago's closest and safest skydiving center

Chicago's best skydiving center with an awesome view of Lake Michigan and the Chicago Skyline!

Open 6-7 days per week, Jump our fast 14 passenger airplane from 14,000 feet above Lake Michigan

Chicago's Best Skydive

Awesome View of Lake/City

Chicago's friendliest skydiving center, now refundable for weather!


Skydive only No Pictures or Video


$209* Groups 2-3
$199* Groups 4-7
$189* Groups 8 or more

* per person


Skydive plus video or pictures - choice at check-in

Pictures OR Video Included


$249* Groups 2-3
$239* Groups 4-7
$229* Groups 8 or more

* per person


Skydive with video and pictures

Pictures AND Video Included


$279* Groups 2-3
$269* Groups 4-7
$259* Groups 8 or more

* per person

VIP Fast Pass

VIP no-waiting package

Pictures AND Video Included


no group or other discounts

includes special pullover, video-editing, and fastest service

Prepay only

Save an extra $30 per person on weekday flex-time skydives

** all discounts (group, flex, birthday, etc..) applied on arrival, not at time of booking. Please Leave Deposit instead of pay-in-full to ensure you get all discounts) **

Price Matching Policy

Book your Skydive Today!

Chicago Skyline View Skydiving

Discounts and Pricing Notes

Discounts Available: Flex-Time Weekday Skydive (you pick the day, we notify you of time the night before): $30 off per person. You may also add one of the following (we apply the best discount you qualify for): Birthday: $20 off if jumping on actual birthday, $10 off if within 7 days of birthday, Military: $20 off if active or retired, $10 off if veteran (proof required), Student $10 off (student ID required), Public Servant: $10 off (proof required). The group discounts can be combined with any of these discounts.

Videos and Pictures: 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)

Online Waiver 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: 2019 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.

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 on the skydiving equipment. If you weigh over 300lbs (on our scale, in your clothing), we cannot skydive with you under any circumstances.

Why Skydive Here? 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 2 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 condtions or air-traffic control limitations.

Discount Vouchers 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.

Price Matching Skydive Windy City Chicago will match published prices of other skydiving centers in our market area (within 75 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.

Book your Skydive Today!

Best Chicago Skydiving

Skydive Windy City Chicago

We are Chicago's closest and best skydive center. We offer services for tandem and licensed jumpers.
We also have a view of Lake Michigan and the Chicago skyline that cannot be matched by any other sky dive center!

Tandem Skydiving

Experience the Thrill!

Tandem Skydiving is the safest, most popular, and most convenient way to experience skydiving. No experience is necessary and a Tandem Skydive is statistically 4 times safer than solo skydiving. We have the fastest service times and best packages in the midwest. Book your skydive online and save money & time.

Video & Pictures

Capture your Jump!

You can add Pictures , Video or both to your experience for very reasonable prices. The pictures and/or video are delivered to you in raw format on via internet link, usually before you leave (usually within 30 minutes of landing). You may have us edit your video and/or receive it on USB for a small extra charge.

Learn to Skydive

Solo Training Program!

If you enjoyed your Tandem as much as most, you may wish to take it a step further. Our Solo Training Program (STP) is a comprehensive program of instruction that helps you earn your United States Parachute Association (USPA) "A" Skydiving license.

Licensed Skydivers

Jump with a view!

Unlike many small dropzones, we allow experienced (licensed) skydivers. With our PAC-750XL 14-passenger jumpship, there are almost always slots available for licensed skydivers and STP (Solo Training Program) students. See the Chicago Skyline and 3 states of Lake Michigan Shoreline during your skydives.

Chicago's Best Skydiving

Email Us Today

We'd love to hear from you!

The Most Amazing Views of Lake Michigan and the Chicago skyline!