AA 4391 then AA 2925 at Boston
Madison → Boston → Chicago O'Hare
Timetable, Boston time
10:23AA 4391 from Madison at the gate
19:38AA 2925 to Chicago O'Hare leaves the gate
9 h 15 apart on the timetable
The last days
AA 4391 and AA 2925 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.