AA 442 then AA 2461 at Boston
Orlando → Boston → Chicago O'Hare
Timetable, Boston time
16:08AA 442 from Orlando at the gate
17:58AA 2461 to Chicago O'Hare leaves the gate
1 h 50 apart on the timetable
Boston’s board gives an arrival time for only about 58% of its flights, so many days show no gate time.
The last days
AA 442 and AA 2461 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.