UA 2160 then UA 5539 at O'Hare
Dallas-Fort Worth → Chicago → Cleveland
Timetable, Chicago time
17:00UA 2160 from Dallas-Fort Worth at the gate
10:50UA 5539 to Cleveland leaves the gate
17 h 50 apart on the timetable, overnight
UA 5539 leaves 17 h 50 after UA 2160 arrives on the timetable: more than half a day, so not a connection we count.