CV 251 then AA 2256 at O'Hare
Anchorage → Chicago → Punta Cana
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
08:14AA 2256 to Punta Cana leaves the gate
13 h 14 apart on the timetable, overnight
AA 2256 leaves 13 h 14 after CV 251 arrives on the timetable: more than half a day, so not a connection we count.