CV 21 then UA 416 at O'Hare
Anchorage → Chicago → Milan
Timetable, Chicago time
22:27CV 21 from Anchorage at the gate
21:35UA 416 to Milan leaves the gate
23 h 08 apart on the timetable, overnight
UA 416 leaves 23 h 08 after CV 21 arrives on the timetable: more than half a day, so not a connection we count.