AA 1007 then UA 3598 at O'Hare
Charlotte Amalie → Chicago → Louisville
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
18:10UA 3598 to Louisville leaves the gate
22 h 10 apart on the timetable, overnight
UA 3598 leaves 22 h 10 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.