AA 9908 then AA 5005 at O'Hare
Milwaukee → Chicago → Cleveland
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
13:45AA 5005 to Cleveland leaves the gate
23 h 55 apart on the timetable, overnight
AA 5005 leaves 23 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.