Below is a list of commonly asked questions about Chicago area skydiving and the city's best skydiving center. Skydive Windy City is Chicago's closest skydive. We offer consistently fast service (almost twice as fast as our competitors), a top safety record for the area, and unmatched views of three states on the Lake Michigan shoreline (Illinois, Indiana, and Michigan) and the beautiful Chicago skyline. On some days we can even see Milwaukee from the air! No other skydiving center can offer you these views or our proximity to the city.