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In winter months, If I'm flying from the Mid-Atlantic or SE US, heading west I don't want (ever) to fly to BWI or MDW for connections ! That's a sure bet to get stranded. Sure wish SWA would help out with more conections via smaller reigional airports. In general, for the traveller, the smaller the airport the better. Large mega airports are a nightmare. We love: PHF, MLB, PBI, AUS, ALB, CLT etc.
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Plus, connecting thru any wagers in the NE or thru MDW in the winter is always a risk!
Have you checked for flights connecting thru DAL, HOU, DEN, or PHX? Given SW’s large operations at these airports (that are either very reasonably sized or contained within one concourse of a larger airport), these are more centrally located.
With that said, given SW’s presence at MDW and BWI, I’m sure we will still see those as popular connection airports. At least BWI has good food options??? 🙂