Join Date: Apr 2009
Location: Bye Delta
Programs: AA EXP, UA Silver, HH Diamond, IHG Plat, Hyatt Plat, Marriott Titanium, Nat'l EE, Avis PC, Hertz PC
Posts: 16,633
I like the E-175s if traveling by myself - no better seat than 1A. With a companion it becomes a bit more of a toss-up.
I find the security lines at MDW to be worse than at ORD if you have Priority access.
No doubt MDW is much closer if you're at McCormick Place. If you're cabbing it to ORD, it's probably twice as far.
MDW tends to get snarled up less than ORD does during adverse weather. On the flip side, if something does go wrong, you will have more alternatives out of ORD.
If you're not going to have lounge access anyway, that's one factor removed from the ORD side of the scales.
I don't think there's really a bad choice here.