AA 1007 then UA 3755 at O'Hare
Charlotte Amalie → Chicago → Louisville
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
16:20UA 3755 to Louisville leaves the gate
20 h 20 apart on the timetable, overnight
UA 3755 leaves 20 h 20 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.