Skydive Windy City Chicago

We're the closest...


Plymouth Sky Sports is now Skydive Windy City Chicago. Operating at the Michigan City Airport in NW Indiana, we are the most convenient skydiving center to Chicago, less than a 1 hour drive from the loop and South suburbs. We have one of the best reputations in the skydiving industry. Come experience skydiving the way it should be, with unmatched amazing views of Lake Michigan shoreline and downtown Chicago that you can't get anywhere else! (219) 210-3338

Chicago Sky Diving

2-jumper DEAL!

Skydiving Deal

If you can jump on a Monday, Tuesday, or Friday, you can save a lot of money with our budget weekday Chicago skydiving deal.



Plymouth Sky Sports
Welcome to Skydive Windy City's landing page.


Plymouth Sky Sports is now Skydive Windy City (Chicago). We are only a 1 hour drive from downtown Chicago or the South suburbs. We are 30 minutes from St. Joseph, South Bend, Valparaiso and South Bend. We are also accessible from Chicago by train via the South Shore Line (Carroll Ave. Station). Skydive Windy City pairs the thrill of jumping out of a perfectly good airplane with unmatched views of beautiful NW Indiana, 3 states of Lake Michigan Shoreline (Illinois, Indiana, and Michigan) and the downtown Chicago skyline just across Lake Michigan. You can call us at (219) 210-3338 or visit our main site directly at

Also check out our amazing deals for your skydive near Chicago:

2016 early season special: 2 for $444 deal running through April 30, 2016 (save $156)


Main Site
Skydive Center Chicago

The best view in the Midwest is near Chicago

Amazing views of 3 states of Lake Michigan shoreline (Illinois, Indiana, and Michigan), and downtown Chicago. The view is unmatched in the midwest!

Chicago's best skydive

Great views out the plane window before you jump

While riding up in our well-maintained airplane, enjoy spectacular views from the windows before you jump out and freefall 120 MPH with 100% pure adrenaline!

Skydive near Chicago

Excitement awaits you at Skydive Windy City

The excitement of a skydive is hard to contain! From arrival to after landing you will have the best and most convenient experience available anywhere!


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