F9 3990 then DL 1665 at Detroit
Dallas-Fort Worth → Detroit → Chicago O'Hare
Timetable, Detroit time
21:43F9 3990 from Dallas-Fort Worth at the gate
19:56DL 1665 to Chicago O'Hare leaves the gate
22 h 13 apart on the timetable, overnight
DL 1665 leaves 22 h 13 after F9 3990 arrives on the timetable: more than half a day, so not a connection we count.