Click here for Pricing notes and discounts

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.

Book your Skydive Today!

Tandem Skydiving

Closest to Chicago

Tandem Skydiving is the most popular and efficient way to experience skydiving. You need no previous experience and will be trained immediately prior to your skydive.
Your instructor...the professional skydiver you will jump with will review and reinforce the training while fitting you to the harness and providing the goggles you will wear on the jump. We have jumpsuits for you to wear if we feel the conditions require it, or you can rent a jumpsuit for a small additional charge.
Once everything is ready, you and your instructor will head to the aircraft for the climb to exit altitude (two miles or more above the earth). During the climb, your instructor will review the jump with you, and "hook up" (attach your harness to the parachute system the instructor wears).
At altitude, you will exit the aircraft with your instructor, freefalling for a mile or more (up to one minute) until you deploy the parachute. On the 4-5 minute parachute ride back to the landing area, you will receive further instruction on how to fly the parachute and find the airport.
After landing, we will remove the harness and associated equipment, provide a certificate/discount card as proof of your skydive, and answer any questions you may have.
If you purchased the video and/or pictures, they are quickly uploaded to the cloud and a link sent to you so you can share them with your friends and family right away.
Skydive Windy City is the only skydiving center in the Chicago Area that jumps next to Lake Michigan and offers skyline views almost every day!
If you are interested in making a Tandem Skydive, book it online from this website, or call us at (219) 210-3338 to make your reservation. We require reservations to be made 5 days in advance to qualify for the group price. When making a reservation, and $50.00 non-refundable deposit will be required per jumper.

Be sure to check out our Chicago Skydiving FAQs page for more information and details about skydiving near chicago.

Customer Testimonials

say the nicest things

Our customers are the lifeblood of our business, without you we would not exist. We strive to provide the safest, fastest, and most comprehensive skydiving experience available anywhere, and out customers notice! Not only do we have the shortest wait times (we value your time), but we also have a top US safety record. We have been in business 7 years and have never had a bad review.

Video and Pictures Information

Video and Pictures are an important part of the skydive, so we offer package deals. When making your first skydive, your brain is overloaded with new sensations and must set aside some functions to process the extreme event. A couple things the brain sets aside are your sense of time (the freefall will feel like 5 seconds long, even though your spectators will assure you it was 35-60+ seconds) and some short-term memory functions. The video and pictures put all that back into place and your brain is whole again. You will watch your video many times and share it with all your friends. You own the rights to the video/pictures once you buy it, and you can post it anywhere you like.

Chicago Area Skydiving

Each week we compile a highlights video of the tandem jumps we made. You can be in the next one video. Check out that view!