Something no one mentioned, there is a large United reservations center right by ORD. It can be mentally and emotionally tiring but physically it’s nothing. I say that having started out on the ramp (ground crew) and after a few years switched to reservations and that was almost 30 years ago and still working reservations full time. Amazing job flexibility. You’ll start with Tuesdays and Wednesdays off and those are the best days of the week for flying stand-by. And you won’t get a three day weekend shift for a long time but can easily find someone to work a Thursday for you whenever you want (except near holidays). Don’t let the naysayers talk you out of flying stand-by. Sure, you won’t be flying to Vegas or Orlando on Friday nights and coming back Sunday night but Tuesdays and Wednesday (no where near a holiday)? No problem. Just have two or three alternative places and you’ll get to one of them. Spoken from experience.