AA 9909 then UA 5827 at O'Hare
Waterloo → Chicago → Washington National
Timetable, Chicago time
17:10AA 9909 from Waterloo at the gate
17:00UA 5827 to Washington National leaves the gate
23 h 50 apart on the timetable, overnight
UA 5827 leaves 23 h 50 after AA 9909 arrives on the timetable: more than half a day, so not a connection we count.