AA 9908 then UA 2620 at O'Hare
Milwaukee → Chicago → Orlando
Timetable, Chicago time
13:50AA 9908 from Milwaukee at the gate
13:30UA 2620 to Orlando leaves the gate
23 h 40 apart on the timetable, overnight
UA 2620 leaves 23 h 40 after AA 9908 arrives on the timetable: more than half a day, so not a connection we count.