2018 Skydiving Information

We are gearing up for the 2018 Skydiving Season.  We will have discounted gift certificates for a short time longer, so if you wish to buy a gift for someone at the discounted holday prices, get on it right away.  Our aircraft is undergoing performance upgrades, so it will be even faster (already we have one of the fastest turbojet aircraft in the country!).  The new equipment is coming in (each year we replace a good portion of our equipment to keep our fleet in top shape.  We sell the older equipment to other dropzones).  Christmas is barely behind us, and we open on April 28, 2018 for the 2018 season.  We have a couple new and exciting products for 2018, including the VIP package, and the Chicago fly-by option, where we fly by downtown chicago before climing to altitude for the skydive.  We hope to see you for another safe skydiving season in 2018!

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The spring 2016 forecast:


The weather forecast for spring looks promising, and our great spring skydive prices will help you save money!  From opening day (April 15) through April 30, you can get our best price of the year for 2 jumpers with video and pictures.  Weekends or Weekdays, it doesn't matter, 2 people skydive close to Chicago for $464, video and pictures included!  Thats only $232 each.  Hold the phone.... you can save another $10 per person by booking online and completing your online waiver (emailed to you after you book).  If you can't make your Chicago skydive in April, the super deal extends to weekdays only in May.  Weekend skydive 2 jumper packages cost $520 ($500 if you book online and do the online waiver) on weekends in May.  The view in the spring is incredible, slightly cooler weather generally means better visibility.  Chicago is just 30 miles away across Lake Michigan, and is usually clearly visible and an impressive vista.  Skydive Windy City Chicago is conveniently located just of I-94 (exit 40B) about 1 hour drive from downtown Chicago.  We are also accessible via South Shore Line (Carroll St. station), so you don't even need a car to come skydive with us.  We hope to see you this spring!

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Chicago's Best Skydiving is almost here for 2016

Skydive Chicago-Style!

Making a skydive in the Chicago area is convenient and affordable.  Not only is Skydive Windy City Chicago the most convenient skydiving center to Chicago, but also have the best view of Lake Michigan and the Dowtown Chicago skyline, great pricing packages as low as $222 per person (video and pictures are included in that price), and one of the fastest service times in the skydiving industry (you don't have to spend all day with us).  We expect to run at near capacity for most of the season, so make your reservations early to ensure you get the date/time you want.  Some dates are already filling up.  

Skydive Windy City Chicago prides itself on unbeatable customer service, a top safety record in the industry (5 years in business and we finished 2015 with zero (0) injuries), the best video and pictures packages, and a life-changing experience for you.  

If you live in the Chicagoland area, Northwest Indiana, or Southwest Michigan, we are the no-brainer choice for your skydiving experience.  Check out our facebook page at https://www.facebook.com/skydivewindycitychicago to see pictures and videos of our operation and customers.  More pictures are available at our Instagram page and our Pinterest page.

If skydiving videos are your thing, you must checkout our Youtube channel.  Every week during the season we compile a weekly highlights video with everyone who jumped with us, making them superstars.  Friends can't belive you did it, prove it to them with our professional video and pictures packages (you take the video and pictures with you when you leave... usually they are ready within 30 minutes of you landing from your tandem skydive).

See you soon!




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The engine is back!

Our engine is back now, and we are hanging it on the airplane today.  At a cost of almost $30,000.00, this type of maintenance is not cheap, but it is imperrative to maintain performance and safety.  Skydiving Safely is always our #1 goal.  We skydive with you, so we have as much to lose as you do.  

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Readiness for the 2016 Skydiving Season

Hello:  Winter is a time we don't make a lot of posts to this blog, but nonetheless things continue to move forward in preparation for the following season.  This year the only team member around is Troy, as he works on the aircraft and (hopefully) the new building construction in prep for the 2016 season.  We sold quite a few gift certificates and took many reservations for the 2016 season before Christmas.

The full season's schedule is up, so if you have a date in mind, pick it early and make your reservation.  You need only leave a $50 deposit per person (it will be applied to your skydive), and it ensures the date and time you want to make your skydive will be reserved.  Your money is in good hands, in 5 full seasons, we have never siezed a deposit.  We want you to skydive.  If we have weather-related reschedules, or if you need to reschedule for your own reasons and give us fair notice (we ask for 5 days), your money will move with your reservation.

The airplane maintenance is coming along, although it has been delayed.  It turns out we spun a main bearing in the engine (not entirely uncommon, but involves more work), so we needed to get the case repaired and get a new crankshaft.  We don't know when this happened, but a new (albeit minor) oil leak developed a couple years ago, and we think that is when it happened.  Goes to show you how durable these motors are.  Since the airplane is down longer than expected, Troy is cleaning up the interior and installing the trim we planned.  Once the engine is done and reinstalled, Troy will fly it to FL to visit his family (this trip was planned for over Xmas & New Years but the delay changed that) and break in the $30K overhauled engine.  The updated engine will take the airplane from 235 horsepower to 285 HP, resulting in faster climb times and less waiting for customers.  The updated engine should last us 5 seasons before it needs major work again.  Exciting times!

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Aircraft Upgrades

As some of you may know, we are upgrading our aircraft over the winter.  Our Cessna 182L, tail number N3400R, has been a fantastic aircraft for us over 5 full seasons of Chicago area Skydiving.  This winter we are overhauling and upgrading the engine.  A normal overhaul would result in a fresh engine with 235 horsepower.  The P-Ponk conversion we are doing will result in a fresh engine with 285+ horsepower.  The propeller has been sent out, inspected, dressed, painted, and rebalanced.  We are also finishing the interior, which was only partially complete in 2015 (panels were up but trim was not).  We have also gone through the entire airplane with a more-thorough-than-required annual inspection.  We repaired the landing gear, including new seals and oil in the strut and new main tires.  Of course all wheel bearings were inspected and regreased and tires balanced.  The upgraded engine was supposed to be back soon but it looks like mid January before we get it back.

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Beanies added to closeout items

Today I added the closeout beanies (Plymouth Sky Sports embroidered logo) to the store.  The shirts are selling faster than I thought, so if you want any of these products don't wait until the ones you want are gone.  Blue Skies and Happy Holidays!

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T-Shirts on sale

Due to the rebranding from Plymouth Sky Sports to Skydive Windy City Chicago during the 2015 season, we have many Plymouth Sky Sports T-Shirts to close out.  We have dropped the prices substantially on these collector item shirts (you won't be able to get these again).  Free shipping on all shirts as well.  We are even selling the left over "Sky Team" shirts.  The only way you could get these shirts before is to be on the team.  Check them out, shirts and hoodies on sale now under the "Store" tab on the website.

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Happy Black Friday Weekend!

Hello Everyone:

We hope your Thanksgiving was relaxing and fulfilling (keyword:  Filling).  As you start preparing for Christmas, remember that you can give the gift of adventure this holiday season... Sky Diving Gift Certificates.  We do have a winter special gift certificate that is good for the entire 2016 season.

 That deal is 2 jumpers for $500 (includes video and pictures for both), which represents at least a $70 savings off normal prices of our 2-jumper deals.

Have a great Black Friday weekend!


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Welcome to our new website


Skydive Windy City (formerly Plymouth Sky Sports) has been in business for 5 full skydiving seasons.  In 2015 a few things happened:

1.  Our home airport decided to rebuild the runway, which would cause us to close the business.

2.  We decided not to close but to move the business to Michigan City, Indiana.

3.  The move makes us the closest skydive center to Chicago.

4.  The move makes us accessible from Chicago by train (South Shore Line - Carroll Ave. Station).

5.  The move also makes us the most scenic skydive in the midwest, skydiving here you can see:

  • 3 states of Lake Michigan Shoreline:  Illinois, Indiana, and Michigan (and sometimes even Wisconsin)
  • The downtown Chicago skyline and cityscape (nowhere else in Chicagoland can you get this view)
  • Beautiful NorthWestern Indiana, including the lakes in LaPorte, Indiana Dunes, and Indiana Beaches

6.  We finished our 5th year in business on November 8, 2015... Injury-free (this means no tandems or licensed skydivers had injuries requiring medical attention).

7.  We designed a new website showcasing our new brand (Skydive Windy City Chicago).


We hope you like the new site design.  It will continue to improve.  We have great gift certificate deals for 2016, check them out.  Our reservations calendar is also up for 2016 so you can start booking your skydive today!

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