I have a flight on the 22nd
LGA-ORD-OGG ...According to the info in MyItineraries it shows there's 27 minutes of time to switch. Seems a little tight to me. The LGA-ORD flight is at 8 am and gets in at 9:33. The ORD-OGG flight leaves at 10 am.
There are earlier flights to ORD, at 7am and at 6 am...I think I shouldn't have too much of a problem having UA switch me to the earlier flight.
Also, there is only 1 ORD-OGG flight that day. I don't want too get stranded at ORD for a whole day