CA 8443 then UA 5637 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
16:00UA 5637 to Milwaukee leaves the gate
23 h 01 apart on the timetable, overnight
UA 5637 leaves 23 h 01 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.