CV 21 then AA 6251 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
22:27CV 21 from Anchorage at the gate
17:24AA 6251 to Milwaukee leaves the gate
18 h 57 apart on the timetable, overnight
AA 6251 leaves 18 h 57 after CV 21 arrives on the timetable: more than half a day, so not a connection we count.