OO 9909 then AA 5005 at O'Hare
Waterloo → Chicago → Cleveland
Timetable, Chicago time
16:47OO 9909 from Waterloo at the gate
13:46AA 5005 to Cleveland leaves the gate
20 h 59 apart on the timetable, overnight
AA 5005 leaves 20 h 59 after OO 9909 arrives on the timetable: more than half a day, so not a connection we count.