AA 9928 then UA 416 at O'Hare
New York LaGuardia → Chicago → Milan
Timetable, Chicago time
06:45AA 9928 from New York LaGuardia at the gate
21:35UA 416 to Milan leaves the gate
14 h 50 apart on the timetable
UA 416 leaves 14 h 50 after AA 9928 arrives on the timetable: more than half a day, so not a connection we count.