CV 251 then AA 9915 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
11:00AA 9915 to Milwaukee leaves the gate
16 h apart on the timetable, overnight
AA 9915 leaves 16 h after CV 251 arrives on the timetable: more than half a day, so not a connection we count.