UA 3908 then AA 2074 at O'Hare
Fort Myers → Chicago → Boston
Timetable, Chicago time
14:19UA 3908 from Fort Myers at the gate
13:37AA 2074 to Boston leaves the gate
23 h 18 apart on the timetable, overnight
AA 2074 leaves 23 h 18 after UA 3908 arrives on the timetable: more than half a day, so not a connection we count.