DL 5614 then AA 1260 at Boston
Milwaukee → Boston → Chicago O'Hare
Timetable, Boston time
17:53DL 5614 from Milwaukee at the gate
16:41AA 1260 to Chicago O'Hare leaves the gate
22 h 48 apart on the timetable, overnight
AA 1260 leaves 22 h 48 after DL 5614 arrives on the timetable: more than half a day, so not a connection we count.