AA 1007 then UA 5984 at O'Hare
Charlotte Amalie → Chicago → Cleveland
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
13:14UA 5984 to Cleveland leaves the gate
17 h 14 apart on the timetable, overnight
UA 5984 leaves 17 h 14 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.