CV 251 then AA 4919 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
10:05AA 4919 to Milwaukee leaves the gate
15 h 05 apart on the timetable, overnight
AA 4919 leaves 15 h 05 after CV 251 arrives on the timetable: more than half a day, so not a connection we count.