DL 2804 then UA 416 at O'Hare
Boston → Chicago → Milan
Timetable, Chicago time
22:36DL 2804 from Boston at the gate
21:35UA 416 to Milan leaves the gate
22 h 59 apart on the timetable, overnight
UA 416 leaves 22 h 59 after DL 2804 arrives on the timetable: more than half a day, so not a connection we count.