Originally Posted by DataPlumber

The "legal" connecting time for Intl to domestic connections at ORD is 1:30. So AA will not even let you ticket the 4:19PM. You'll have to ticket on the 8:05PM and then standby if you make it to T3 in time for the earlier flight.

The issue is how long it will take to take the Tram from T5 (Intl) to T3 (AA) and reclear security. I've heard of it done in an hour or so, but if you are delayed in customs or waiting for the tram you'll miss the 4:19 flight.