CA 3103 then AS 9915 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
15:07CA 3103 from Anchorage at the gate
14:24AS 9915 to Milwaukee leaves the gate
23 h 17 apart on the timetable, overnight
AS 9915 leaves 23 h 17 after CA 3103 arrives on the timetable: more than half a day, so not a connection we count.