AA 3309 then AA 5229 at Charlotte
Milwaukee → Charlotte → Roanoke
Timetable, Charlotte time
15:31AA 3309 from Milwaukee at the gate
12:40AA 5229 to Roanoke leaves the gate
21 h 09 apart on the timetable, overnight
AA 5229 leaves 21 h 09 after AA 3309 arrives on the timetable: more than half a day, so not a connection we count.