AA 9909 then AS 325 at O'Hare
Waterloo → Chicago → Portland (Oregon)
Timetable, Chicago time
17:10AA 9909 from Waterloo at the gate
14:07AS 325 to Portland (Oregon) leaves the gate
20 h 57 apart on the timetable, overnight
AS 325 leaves 20 h 57 after AA 9909 arrives on the timetable: more than half a day, so not a connection we count.