CA 1055 then AA 4992 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
22:20CA 1055 from Anchorage at the gate
21:35AA 4992 to Milwaukee leaves the gate
23 h 15 apart on the timetable, overnight
AA 4992 leaves 23 h 15 after CA 1055 arrives on the timetable: more than half a day, so not a connection we count.