AA 9909 then UA 5565 at O'Hare
Waterloo → Chicago → Charlottesville
Timetable, Chicago time
17:10AA 9909 from Waterloo at the gate
14:10UA 5565 to Charlottesville leaves the gate
21 h apart on the timetable, overnight
UA 5565 leaves 21 h after AA 9909 arrives on the timetable: more than half a day, so not a connection we count.