CA 8443 then UA 4166 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
10:42UA 4166 to Madison leaves the gate
17 h 43 apart on the timetable, overnight
UA 4166 leaves 17 h 43 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.