AA 9908 then UA 4452 at O'Hare
Milwaukee → Chicago → Richmond
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:59UA 4452 to Richmond leaves the gate
21 h 09 apart on the timetable, overnight
UA 4452 leaves 21 h 09 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.