AA 1007 then UA 5566 at O'Hare
Charlotte Amalie → Chicago → Pittsburgh
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
15:50UA 5566 to Pittsburgh leaves the gate
19 h 50 apart on the timetable, overnight
UA 5566 leaves 19 h 50 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.