A FlyerTalk Posting Legend
Join Date: Jul 2002
Location: MCI
Programs: AA Gold 1MM, AS MVP, UA Silver, WN A-List, Marriott LT Titanium, HH Diamond
Posts: 52,551
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.
Some would argue that DCA isn't even 45 minutes worse, given that it's much easier to rent a car and easier to get in, out, and through the airport in general. I spent years commuting in/out of DCA, sometimes renting a car, sometimes using taxis or Metro, and even a year or so parking my own car. It was always easier than IAD.