Very sorry to hear about your grandfather! I've gone through it once before, and hope that I don't have to go through it for a long time!!

As far as AA, was there no way for you to get to ORD that night, and then fly first thing on the 5th? If you could have gotten to IAD, UA187 would have gotten you to IAD at 9:30am.

Considering the fact that you fly so much, I feel as though you should have factored in the possibility for a delay/cancellation. I would have gone out of JFK much earlier in the day, rather than waiting until the evening... My $0.02.