AA 1007 then UA 1066 at O'Hare
Charlotte Amalie → Chicago → Houston
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
17:23UA 1066 to Houston leaves the gate
21 h 23 apart on the timetable, overnight
UA 1066 leaves 21 h 23 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.