AA 9909 then UA 2182 at O'Hare
Waterloo → Chicago → Portland (Oregon)
Timetable, Chicago time
17:10AA 9909 from Waterloo at the gate
12:49UA 2182 to Portland (Oregon) leaves the gate
19 h 39 apart on the timetable, overnight
UA 2182 leaves 19 h 39 after AA 9909 arrives on the timetable: more than half a day, so not a connection we count.