CA 8443 then UA 5933 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
12:29UA 5933 to Milwaukee leaves the gate
19 h 30 apart on the timetable, overnight
UA 5933 leaves 19 h 30 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.