If I don't have to, I don't fly (just don't like it). On that premises, if I were you, I'd go to the DC one (I see that you live in Virginia).
As for me, if I were home in NY, I think I would still go to the DC one - Chicago is not a far drive from NY, but you can take the train from NY to DC, which leads to a much more relaxing ride. Instead of driving and watching out for crazy drivers, you can sleep/read/mess around on the computer.
And no parking when you get to either city (I hate finding/paying for parking!)
I'd say DC ~ (If I weren't in Hong Kong