AA 9908 then UA 3422 at O'Hare
Milwaukee → Chicago → Cleveland
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
09:00UA 3422 to Cleveland leaves the gate
19 h 10 apart on the timetable, overnight
UA 3422 leaves 19 h 10 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.