AA 4360 then UA 5201 at O'Hare
Cleveland → Chicago → Milwaukee
Timetable, Chicago time
05:59AA 4360 from Cleveland at the gate
20:00UA 5201 to Milwaukee leaves the gate
14 h 01 apart on the timetable
UA 5201 leaves 14 h 01 after AA 4360 arrives on the timetable: more than half a day, so not a connection we count.