AA 1409 then AA 5543 at Charlotte
Chicago O'Hare → Charlotte → Pittsburgh
Timetable, Charlotte time
16:27AA 1409 from Chicago O'Hare at the gate
08:30AA 5543 to Pittsburgh leaves the gate
16 h 03 apart on the timetable, overnight
AA 5543 leaves 16 h 03 after AA 1409 arrives on the timetable: more than half a day, so not a connection we count.