DL 5619 then AA 2925 at Boston
Milwaukee → Boston → Chicago O'Hare
Timetable, Boston time
22:02DL 5619 from Milwaukee at the gate
19:40AA 2925 to Chicago O'Hare leaves the gate
21 h 38 apart on the timetable, overnight
AA 2925 leaves 21 h 38 after DL 5619 arrives on the timetable: more than half a day, so not a connection we count.