The Boca Raton (KBCT) to Chicago Midway (KMDW) route is a popular private jet connection between South Florida and the Chicago area. Ideal for business travelers, seasonal residents, families, and weekend trips, this route provides convenient access to downtown Chicago while avoiding the crowds and schedules of major commercial airports. Let’s Fly Private can arrange aircraft ranging from light and midsize jets to super-midsize and heavy jets, with departure times built around your schedule.