OO 9909 then UA 5890 at O'Hare
Waterloo → Chicago → Charlottesville
Timetable, Chicago time
16:47OO 9909 from Waterloo at the gate
10:25UA 5890 to Charlottesville leaves the gate
17 h 38 apart on the timetable, overnight
UA 5890 leaves 17 h 38 after OO 9909 arrives on the timetable: more than half a day, so not a connection we count.