Skydive Windy City Chicago

Chicago's closest and safest skydiving center

The only skydive center with an awesome view of Lake Michigan and the Chicago skyline almost every day!

All customers completing their skydive before May 31st will receive a free special t-shirt!

(while supplies last)

Skydive next to Lake Michigan

See the Chicago skyline

All customers completing their skydive before May 31st will receive a free special t-shirt!

(while supplies last)


Skydive only No Pictures or Video

$218 (single jumper)

$208* Groups 2-3
$198* Groups 4-7
$188* Groups 8 or more

per person


Skydive plus video or pictures - choice at check-in

Pictures OR Video Included

$268 (single jumper)

$248* Groups 2-3
$238* Groups 4-7
$228* Groups 8 or more

* per person


Skydive with video and pictures

Pictures AND Video Included

$298 (single jumper)

$278* Groups 2-3
$268* Groups 4-7
$258* Groups 8 or more

* per person

VIP Fast Pass

VIP no-waiting package

Pictures AND Video Included

$389 (per jumper)

no group or other discounts

includes special t-shirt, video-editing, and customer certificate

Prepay only

Save up to an extra $40 per person on weekday skydives

** $20 flex-time discount (must book flex-time), and $20 weekday discount **

** all group, weekday, and other discounts applied on arrival, not at time of booking **

Chicago Skyline Fly-By Skydive

Book your Skydive Today!

Chicago's Most Scenic Skydive

Discounts and Pricing Notes

Discounts Available: Weekday Skydive: $20 off, Flex-Time Skydive: $20 off (can be combined with weekday discount), 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).

Video and Pictures: Add pictures or video (choose at check-in) to bronze or voucher skydive for $68, Add Video and Pictures to bronze or voucher skydive for $98, Add video editing $10, Add USB drive (standard is email link within 24 hours) $15

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 will 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: 2018 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 2018 waiver, you are good for all of 2018). We have the lowest package prices in Chicagoland and this allows us to provide efficient customer service, and keeps your on-site time as low as possible.

Maximum weight for height: All jumpers must be under the maximum weight for their height according to our height/weight chart. If you are between 210 and 239 pounds (and under max weight for height), you will be charged an extra $30.00 for your skydive. If you are between 240 and 270 pounds (and under max weight for height), you will be charged an extra $50.00 for your skydive. We can skydive safely with many people between 210 and 270 pounds, but it is much more work for the instructor and creates more wear & tear on the skydiving equipment.

Why Skydive Here? The Chicago area provides a number of choices for skydiving, and no matter where you go, the skydive is roughly the same (amazing). What is different about each Skydiving Center is their location and proximity to you. We have the best location for views of Chicagoland, and are closest to the city of Chicago (especially if you are south of 290). We jump 2 miles from Lake Michigan in Michigan City, Indiana, are only an hour 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 hope you have a great time, but if you want the most out of it, 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 From time-to-time we may offer discount skydiving vouchers through a 3rd 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.

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

Chicago Area Skydiving

Skydive Windy City Chicago

We are Chicago's closest and most convenient 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 Parachuting is the most popular way to experience the thrill of skydiving. No experience is necessary and Tandem 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. See our 2018 altitude upgrade options.

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.

Solo Training

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.

Experienced Skydivers

Jump with a view!

Unlike many small dropzones, we allow experienced (licensed) skydivers. With our Cessna 208-114A jumpship, there are almost always slots available for experienced skydivers and STP (Solo Training Program) students. See the Chicago Skyline and 3 states of Lake Michigan Shoreline during your skydives.

Chicago's Best Sky Diving

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We'd love to hear from you!

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