DL 5619 then DL 5609 at Boston
Milwaukee → Boston → New York LaGuardia
Timetable, Boston time
22:02DL 5619 from Milwaukee at the gate
21:00DL 5609 to New York LaGuardia leaves the gate
22 h 58 apart on the timetable, overnight
DL 5609 leaves 22 h 58 after DL 5619 arrives on the timetable: more than half a day, so not a connection we count.