DL 2804 then AA 4992 at O'Hare
Boston → Chicago → Milwaukee
Timetable, Chicago time
21:51DL 2804 from Boston at the gate
21:35AA 4992 to Milwaukee leaves the gate
23 h 44 apart on the timetable, overnight
AA 4992 leaves 23 h 44 after DL 2804 arrives on the timetable: more than half a day, so not a connection we count.