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  1. 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.

  2. 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.

  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 route map - from Chicago Midway is presented on this page | AirlineRouteMaps.com – world’s largest online airline route map database with over 1200 maps from nearly 800 airlines in 200 countries.

  5. Visit one of America's historic cities with a flight to Detroit on Southwest Airlines®. We have nonstop flights and low fares to Michigan for your next trip.

  6. Detailed flight information from Orlando MCO to Chicago ORD. See all airline(s) with scheduled flights and weekly timetables up to 9 months ahead. Flightnumbers and complete route information.

  7. 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.