Originally Posted by
UKtravelbear
Also AA have a history of lots of schedule changes so whilst I would book it I'd be looking at the booking on a Monday to see if it has changed - AA do schedule changes on a weekend.
+1
Downside: you need to be on top of your bookings, ideally using one of many apps to send a ping when AA fiddles with them. And check, often.
Upside: if they do, then ring them as the agents have (IME) a lot of freedom to rebook you any way that's remotely reasonable and sometimes they overdeliver (eg. once had them adjust the outbound which hadn't changed, as well as the return which they had retimed). It's a massive free option to play
At ORD, the Hilton was historically more than adequate, though I haven't been for a few years. It's directly opposite terminals. They used to run a "Christmas in July" sale as well. If you have time to go into town, subway directly below.