AA 9950 then UA 2287 at O'Hare
Philadelphia → Chicago → Sarasota
Timetable, Chicago time
13:49AA 9950 from Philadelphia at the gate
11:44UA 2287 to Sarasota leaves the gate
21 h 55 apart on the timetable, overnight
UA 2287 leaves 21 h 55 after AA 9950 arrives on the timetable: more than half a day, so not a connection we count.