BR 608 then AA 4919 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
20:03BR 608 from Anchorage at the gate
10:05AA 4919 to Milwaukee leaves the gate
14 h 02 apart on the timetable, overnight
AA 4919 leaves 14 h 02 after BR 608 arrives on the timetable: more than half a day, so not a connection we count.