ET 3608 then UA 416 at O'Hare
Anchorage → Chicago → Milan
Timetable, Chicago time
07:16ET 3608 from Anchorage at the gate
21:35UA 416 to Milan leaves the gate
14 h 19 apart on the timetable
UA 416 leaves 14 h 19 after ET 3608 arrives on the timetable: more than half a day, so not a connection we count.