AA 5331 then F9 1342 at DFW
Midland → Dallas-Fort Worth → Chicago O'Hare
Timetable, Dallas-Fort Worth time
08:40AA 5331 from Midland at the gate
06:55F9 1342 to Chicago O'Hare leaves the gate
22 h 15 apart on the timetable, overnight
F9 1342 leaves 22 h 15 after AA 5331 arrives on the timetable: more than half a day, so not a connection we count.