AS 262 then AS 429 at Seattle
Cleveland → Seattle → Chicago O'Hare
Timetable, Seattle time
10:24AS 262 from Cleveland at the gate
11:23AS 429 to Chicago O'Hare leaves the gate
59 min apart on the timetable
Seattle’s board gives a departure time for only about 56% of its flights, so many days show no gate time.
The last days
AS 262 and AS 429 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.