AA 975 then UA 5539 at O'Hare
Montego Bay → Chicago → Cleveland
Timetable, Chicago time
19:46AA 975 from Montego Bay at the gate
10:45UA 5539 to Cleveland leaves the gate
14 h 59 apart on the timetable, overnight
UA 5539 leaves 14 h 59 after AA 975 arrives on the timetable: more than half a day, so not a connection we count.