AA 1249 then AA 2423 at Charlotte
Pensacola → Charlotte → Chicago O'Hare
Timetable, Charlotte time
14:49AA 1249 from Pensacola at the gate
14:47AA 2423 to Chicago O'Hare leaves the gate
23 h 58 apart on the timetable, overnight
AA 2423 leaves 23 h 58 after AA 1249 arrives on the timetable: more than half a day, so not a connection we count.