UA 5337 then AA 9912 at O'Hare
Green Bay → Chicago → Richmond
Timetable, Chicago time
09:37UA 5337 from Green Bay at the gate
07:30AA 9912 to Richmond leaves the gate
21 h 53 apart on the timetable, overnight
AA 9912 leaves 21 h 53 after UA 5337 arrives on the timetable: more than half a day, so not a connection we count.