Aviation SWA to launch Caribbean flights from Chicago Midway By Jerry Limone / January 11, 2013 Share 1 -- Southwest Airlines this spring will launch service from Chicago Midway to two Caribbean destinations: Montego Bay, Jamaica, and Punta Cana, Dominican Republic. Southwest’s AirTran subsidiary will operate the flights. Tickets are on sale for both routes. The Montego Bay service will start April 14 and operate on Mondays, Tuesdays, Fridays and Sundays. Punta Cana flights will begin May 19 and operate on Mondays, Thursdays, Saturdays and Sundays. No other airline flies to the two Caribbean destinations from Midway, but United flies to both seasonally from Chicago O’Hare. American flies seasonally to Montego Bay from O’Hare, and Frontier Airlines operates charters to both destinations from O’Hare for Apple Vacations.