From what I see from all the internet tough guys, it should be tougher than it could be because around half the flights are on Eagle. Since you're supposedly scum by wanting to go to PSA.

For real though, I would say any of the PSA bases from ORD wouldn't be too terrible. It's all 50 seaters, or for the most part to DAY and TYS. Airways has all mainline to CLT. But just be aware as the integration moves on, it will become full blown hub to hub, which can be difficult. I would say there is no such thing as a good or easy commute. Personally, I would pick the most junior base and then go with CLT as you get more senior. CLT-ORD has some flights that go very late, so that would be more beneficial to you on go home day.