DL 5614 then AA 4443 at Boston
Milwaukee → Boston → New York LaGuardia
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
15:20AA 4443 to New York LaGuardia leaves the gate
21 h 27 apart on the timetable, overnight
AA 4443 leaves 21 h 27 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.