UA 1107 then UA 5539 at O'Hare
Tampa → Chicago → Cleveland
Timetable, Chicago time
21:00UA 1107 from Tampa at the gate
10:50UA 5539 to Cleveland leaves the gate
13 h 50 apart on the timetable, overnight
UA 5539 leaves 13 h 50 after UA 1107 arrives on the timetable: more than half a day, so not a connection we count.