AA 9908 then UA 5917 at O'Hare
Milwaukee → Chicago → Roanoke
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:25UA 5917 to Roanoke leaves the gate
20 h 35 apart on the timetable, overnight
UA 5917 leaves 20 h 35 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.