CV 251 then AA 4384 at O'Hare
Anchorage → Chicago → Pensacola
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
11:32AA 4384 to Pensacola leaves the gate
16 h 32 apart on the timetable, overnight
AA 4384 leaves 16 h 32 after CV 251 arrives on the timetable: more than half a day, so not a connection we count.