CA 8443 then UA 5407 at O'Hare
Anchorage → Chicago → Appleton
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:30UA 5407 to Appleton leaves the gate
21 h 31 apart on the timetable, overnight
UA 5407 leaves 21 h 31 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.