CV 251 then UA 764 at O'Hare
Anchorage → Chicago → Calgary
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
08:40UA 764 to Calgary leaves the gate
13 h 40 apart on the timetable, overnight
UA 764 leaves 13 h 40 after CV 251 arrives on the timetable: more than half a day, so not a connection we count.