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  1. There are 156 weekly flights from Orlando to Chicago (Midway) on Southwest Airlines. Does Southwest fly nonstop on weekdays from Orlando to Chicago (Midway)? Yes, Southwest flies nonstop from Orlando to Chicago (Midway) 7 times per day from Monday through Friday.

  2. Use our route map to explore where Southwest flies and plan your next trip with Southwest Airlines. Search and find flights by city, date, and airport.

  3. All Southwest Airlines flights on an interactive flight map, including Southwest Airlines timetables and flight schedules. Find Southwest Airlines routes, destinations and airports, see where they fly and book your flight!

  4. Southwest Airlines Destinations and flight schedules from and to Orlando Airport (MCO)

  5. Find flights to Detroit from $35. Fly from Orlando on Frontier, Spirit Airlines and more. Search for Detroit flights on KAYAK now to find the best deal.

  6. Orlando (MCO) to Chicago (MDW) flight schedule. The monthly calendar shows every direct flight departure from Orlando International (MCO) with all airlines. Click on a date to see a list of flights or search for the best prices. All weekly departures with Southwest Airlines.

  7. Follow the links below in order to see all the flights scheduled for Southwest Airlines. - Southwest Airlines Arrivals. - Southwest Airlines Departures. Check-in. In order to check in for your flight at Chicago Midway Airport (MDW), go to the departures zone of the terminal, or follow the instructions provided in your ticket.