Skydive Windy City is Chicago’s closest skydiving center, and the most scenic skydive in the midwest. Jump next to Lake Michigan with an incredible view of the entire southern tip of the lake, including the Chicago skyline. We have great prices, the fastest service times in the midwest, and one of the best reputations in the country. Skydiving is an amazing experience wherever you do it, but add a breathtaking view and your choice should be simple! Located at the Michigan City Airport, less than 1 hour from downtown Chicago.