AA 3309 then AA 5133 at Charlotte
Milwaukee → Charlotte → Richmond
Timetable, Charlotte time
15:31AA 3309 from Milwaukee at the gate
13:55AA 5133 to Richmond leaves the gate
22 h 24 apart on the timetable, overnight
AA 5133 leaves 22 h 24 after AA 3309 arrives on the timetable: more than half a day, so not a connection we count.