AA 1007 then AA 5005 at O'Hare
Charlotte Amalie → Chicago → Cleveland
Timetable, Chicago time
20:00AA 1007 from Charlotte Amalie at the gate
13:46AA 5005 to Cleveland leaves the gate
17 h 46 apart on the timetable, overnight
AA 5005 leaves 17 h 46 after AA 1007 arrives on the timetable: more than half a day, so not a connection we count.