Thank you everyone for the posts. I appreciate the info regarding the layover times.

Also, I think I'm just green behind the ears and got excited over the whole "miles and points" thing once I learned I could basically get free points and miles since work pays for it all.

One thing is that if I *do* use MKE (usually $30 to $50 cheaper than ORD), most of the United flights I find include connections as well, and so if using MKE, I think using Delta would be okay since I'd have to connect anyway (AA connects too).

But y'all are right...for DCA to ORD, it would be more appropriate for a nonstop flight. Like I said, I got a little excited and jumped the gun (however, I may be flying to India via AF so maybe it won't be a completely dumb decision). The extra time, the risk of connecting flights, and also flying on smaller/not-as-nice planes due to segments sort of make this seem silly. I shouldn't have based my decision based on CC availability. To that point though, I can still get an AA Citi card I believe.

Thanks all for the help.