CA 8443 then AS 325 at O'Hare
Anchorage → Chicago → Portland (Oregon)
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:07AS 325 to Portland (Oregon) leaves the gate
21 h 08 apart on the timetable, overnight
AS 325 leaves 21 h 08 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.