DL 5359 then UA 5381 at Detroit
Cleveland → Detroit → Chicago O'Hare
Timetable, Detroit time
15:14DL 5359 from Cleveland at the gate
14:09UA 5381 to Chicago O'Hare leaves the gate
22 h 55 apart on the timetable, overnight
UA 5381 leaves 22 h 55 after DL 5359 arrives on the timetable: more than half a day, so not a connection we count.