AA 9909 then UA 3755 at O'Hare
Waterloo → Chicago → Louisville
Timetable, Chicago time
17:10AA 9909 from Waterloo at the gate
16:20UA 3755 to Louisville leaves the gate
23 h 10 apart on the timetable, overnight
UA 3755 leaves 23 h 10 after AA 9909 arrives on the timetable: more than half a day, so not a connection we count.