CA 8443 then AS 9915 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
16:59CA 8443 from Anchorage at the gate
14:24AS 9915 to Milwaukee leaves the gate
21 h 25 apart on the timetable, overnight
AS 9915 leaves 21 h 25 after CA 8443 arrives on the timetable: more than half a day, so not a connection we count.