AA 4414 then AA 888 at Boston
Madison → Boston → Chicago O'Hare
Timetable, Boston time
11:16AA 4414 from Madison at the gate
16:47AA 888 to Chicago O'Hare leaves the gate
5 h 31 apart on the timetable
The last days
AA 4414 and AA 888 weren’t both flown 15 min to 12 h apart in the last 21 days.
Statistics from past flights, not live flight information. Always check times and your connection with your airline, and don’t base travel or booking decisions on these numbers.