OO 225 then DL 2985 at O'Hare
Richmond → Chicago → New York LaGuardia
Timetable, Chicago time
11:48OO 225 from Richmond at the gate
11:30DL 2985 to New York LaGuardia leaves the gate
23 h 42 apart on the timetable, overnight
DL 2985 leaves 23 h 42 after OO 225 arrives on the timetable: more than half a day, so not a connection we count.