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For a flight that short, it doesn't really matter. Go with the one that fits your strategy for the whole year
I'm out of ORD and fly American. What I here from my United flier peers is that unless you have top status, status means almost nothing because everybody flying out of O'hare during the week has United Status. More flight options for United though, so pros/cons to either
I do American for DCA-ORD and as only platinum get upgraded often
Upgrades to First? I get economy plus with my United silver most of the time. Is that equiv to plat on American? Assuming no
I get first when using the 500 mile upgrades, which are required for anything below exec plat. American Plat is similar to Gold on united
Frequency of DCA - ORD is much higher for United (hourly). Having status helps me move my flights up or down as convenient. I will confess to not knowing AA's flexibility here, but this helps me a lot. On the other hand, T1 at ORD is a bit more of a pain than T3 during the morning hours.