DL 5619 then UA 2229 at Boston
Milwaukee → Boston → Chicago O'Hare
Timetable, Boston time
22:02DL 5619 from Milwaukee at the gate
20:25UA 2229 to Chicago O'Hare leaves the gate
22 h 23 apart on the timetable, overnight
UA 2229 leaves 22 h 23 after DL 5619 arrives on the timetable: more than half a day, so not a connection we count.