UA 1775 then AA 1976 at O'Hare
Washington → Chicago → Puerto Vallarta
Timetable, Chicago time
09:45UA 1775 from Washington at the gate
08:43AA 1976 to Puerto Vallarta leaves the gate
22 h 58 apart on the timetable, overnight
AA 1976 leaves 22 h 58 after UA 1775 arrives on the timetable: more than half a day, so not a connection we count.