AA 1007 then UA 5854 at O'Hare
Charlotte Amalie → Chicago → Lexington
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
16:30UA 5854 to Lexington leaves the gate
20 h 30 apart on the timetable, overnight
UA 5854 leaves 20 h 30 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.