AA 1007 then UA 5985 at O'Hare
Charlotte Amalie → Chicago → Cleveland
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
16:27UA 5985 to Cleveland leaves the gate
20 h 27 apart on the timetable, overnight
UA 5985 leaves 20 h 27 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.