CA 8443 then UA 5530 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
13:59UA 5530 to Madison leaves the gate
21 h apart on the timetable, overnight
UA 5530 leaves 21 h after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.