AA 9950 then AA 4919 at O'Hare
Philadelphia → Chicago → Milwaukee
Timetable, Chicago time
13:49AA 9950 from Philadelphia at the gate
10:05AA 4919 to Milwaukee leaves the gate
20 h 16 apart on the timetable, overnight
AA 4919 leaves 20 h 16 after AA 9950 arrives on the timetable: more than half a day, so not a connection we count.