UA 2220 then DL 5665 at Boston
Chicago O'Hare → Boston → Richmond
Timetable, Boston time
15:36UA 2220 from Chicago O'Hare at the gate
15:23DL 5665 to Richmond leaves the gate
23 h 47 apart on the timetable, overnight
DL 5665 leaves 23 h 47 after UA 2220 arrives on the timetable: more than half a day, so not a connection we count.