UA 5639 then AA 9908 at O'Hare
Winnipeg → Chicago → Milwaukee
Timetable, Chicago time
16:50UA 5639 from Winnipeg at the gate
10:00AA 9908 to Milwaukee leaves the gate
17 h 10 apart on the timetable, overnight
AA 9908 leaves 17 h 10 after UA 5639 arrives on the timetable: more than half a day, so not a connection we count.