OO 9909 then UA 4448 at O'Hare
Waterloo → Chicago → Roanoke
Timetable, Chicago time
16:47OO 9909 from Waterloo at the gate
14:10UA 4448 to Roanoke leaves the gate
21 h 23 apart on the timetable, overnight
UA 4448 leaves 21 h 23 after OO 9909 arrives on the timetable: more than half a day, so not a connection we count.