AA 9908 then UA 5748 at O'Hare
Milwaukee → Chicago → Traverse City
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
11:20UA 5748 to Traverse City leaves the gate
21 h 30 apart on the timetable, overnight
UA 5748 leaves 21 h 30 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.