AA 9908 then UA 2220 at O'Hare
Milwaukee → Chicago → Boston
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
12:11UA 2220 to Boston leaves the gate
22 h 21 apart on the timetable, overnight
UA 2220 leaves 22 h 21 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.