AA 9908 then UA 4505 at O'Hare
Milwaukee → Chicago → Huntsville
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:35UA 4505 to Huntsville leaves the gate
20 h 45 apart on the timetable, overnight
UA 4505 leaves 20 h 45 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.