CA 1011 then AA 4992 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
04:54CA 1011 from Anchorage at the gate
21:35AA 4992 to Milwaukee leaves the gate
16 h 41 apart on the timetable
AA 4992 leaves 16 h 41 after CA 1011 arrives on the timetable: more than half a day, so not a connection we count.