AA 1007 then UA 5838 at O'Hare
Charlotte Amalie → Chicago → Louisville
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
14:30UA 5838 to Louisville leaves the gate
18 h 30 apart on the timetable, overnight
UA 5838 leaves 18 h 30 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.