AA 9908 then UA 3600 at O'Hare
Milwaukee → Chicago → Raleigh-Durham
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
09:05UA 3600 to Raleigh-Durham leaves the gate
19 h 15 apart on the timetable, overnight
UA 3600 leaves 19 h 15 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.