AA 1007 then UA 1369 at O'Hare
Charlotte Amalie → Chicago → Washington National
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
18:00UA 1369 to Washington National leaves the gate
22 h apart on the timetable, overnight
UA 1369 leaves 22 h after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.