CA 8443 then UA 5362 at O'Hare
Anchorage → Chicago → Duluth
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
12:40UA 5362 to Duluth leaves the gate
19 h 41 apart on the timetable, overnight
UA 5362 leaves 19 h 41 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.