DL 5614 then AA 2881 at Boston
Milwaukee → Boston → Washington National
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
17:25AA 2881 to Washington National leaves the gate
23 h 32 apart on the timetable, overnight
AA 2881 leaves 23 h 32 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.