AA 1007 then UA 4535 at O'Hare
Charlotte Amalie → Chicago → Pittsburgh
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
12:48UA 4535 to Pittsburgh leaves the gate
16 h 48 apart on the timetable, overnight
UA 4535 leaves 16 h 48 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.