DL 2804 then AA 6257 at O'Hare
Boston → Chicago → Milwaukee
Timetable, Chicago time
22:36DL 2804 from Boston at the gate
21:34AA 6257 to Milwaukee leaves the gate
22 h 58 apart on the timetable, overnight
AA 6257 leaves 22 h 58 after DL 2804 arrives on the timetable: more than half a day, so not a connection we count.