AA 9950 then AA 2074 at O'Hare
Philadelphia → Chicago → Boston
Timetable, Chicago time
13:49AA 9950 from Philadelphia at the gate
13:37AA 2074 to Boston leaves the gate
23 h 48 apart on the timetable, overnight
AA 2074 leaves 23 h 48 after AA 9950 arrives on the timetable: more than half a day, so not a connection we count.