UA 6097 then UA 5539 at O'Hare
White Plains → Chicago → Cleveland
Timetable, Chicago time
16:00UA 6097 from White Plains at the gate
10:50UA 5539 to Cleveland leaves the gate
18 h 50 apart on the timetable, overnight
UA 5539 leaves 18 h 50 after UA 6097 arrives on the timetable: more than half a day, so not a connection we count.