DL 5359 then WN 2631 at Detroit
Cleveland → Detroit → Chicago Midway
Timetable, Detroit time
15:14DL 5359 from Cleveland at the gate
13:30WN 2631 to Chicago Midway leaves the gate
22 h 16 apart on the timetable, overnight
WN 2631 leaves 22 h 16 after DL 5359 arrives on the timetable: more than half a day, so not a connection we count.