AA 562 then UA 5539 at O'Hare
Portland (Oregon) → Chicago → Cleveland
Timetable, Chicago time
19:44AA 562 from Portland (Oregon) at the gate
10:45UA 5539 to Cleveland leaves the gate
15 h 01 apart on the timetable, overnight
UA 5539 leaves 15 h 01 after AA 562 arrives on the timetable: more than half a day, so not a connection we count.