CV 2095 then AA 6257 at O'Hare
Anchorage → Chicago → Milwaukee
Timetable, Chicago time
22:35CV 2095 from Anchorage at the gate
21:34AA 6257 to Milwaukee leaves the gate
22 h 59 apart on the timetable, overnight
AA 6257 leaves 22 h 59 after CV 2095 arrives on the timetable: more than half a day, so not a connection we count.