AA 4499 then AA 9867 at O'Hare
Charlottesville → Chicago → Springfield Branson National
Timetable, Chicago time
08:32AA 4499 from Charlottesville at the gate
06:30AA 9867 to Springfield Branson National leaves the gate
21 h 58 apart on the timetable, overnight
AA 9867 leaves 21 h 58 after AA 4499 arrives on the timetable: more than half a day, so not a connection we count.