Originally Posted by
pinniped
If Midway is your more convenient Chicago airport, then WN to DCA is going to be by far your best bet. Worst case - your office is right by IAD - DCA is really only 45 minutes or so worse than IAD, so no connecting flight is ever going to be worth your time.
Since OP's "next project will be in western VA," the 45-minute argument in DCA's favor doesn't apply.
AirTran's DCA slots were critical to WN's acquisition. Five years earlier, WN launched IAD:
Southwest Airlines will begin its Dulles service with a total of 12 daily nonstop departures to the following cities: Chicago Midway (seven daily), Las Vegas (one daily), Orlando (two daily), and Tampa Bay (two daily). The airline will offer direct or connecting service to 35 other destinations such as Denver, Ft. Lauderdale/Hollywood, and Los Angeles.
"Dulles will be a fantastic complement to our Baltimore/Washington operation," Kelly said. "Our Customers in Washington, D.C., and the surrounding areas now have another excellent choice of airports when they want Southwest Airlines' convenient, low-fare service."