These transportation options in Orland Park might help your romantic trip get off to a smooth start: To get to Orland Park, book a flight to Chicago Midway Airport (MDW), which is the closest major airport, located 12.4 mi (19.9 km) from the city center. If you want to journey outside of the area, ride aboard a train from Orland Park 143rd Street Station, Orland Park 153rd Street Station, or Orland Park 179th Street Station.