AA 9908 then UA 2414 at O'Hare
Milwaukee → Chicago → Nashville
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
10:45UA 2414 to Nashville leaves the gate
20 h 55 apart on the timetable, overnight
UA 2414 leaves 20 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.