Windy City Flyers is a premier flight school and aircraft rental club located at the Chicago Executive Airport (KPWK) Windy City Flyers has trained thousands of pilots using a structured program that allows you to move at your own pace. With the largest rental and training fleet in the Chicagoland area, we recognize the need for superior customer service, professional flight instructors and expert aircraft maintenance. Scheduled flying lessons and aircraft rentals are available 24 hours a day, 7 days a week.