AA 9908 then UA 1660 at O'Hare
Milwaukee → Chicago → Seattle (SEA)
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:45UA 1660 to Seattle (SEA) leaves the gate
22 h 55 apart on the timetable, overnight
UA 1660 leaves 22 h 55 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.