S9 290 then AC 7164 at Toronto Pearson
Chicago Midway → Toronto → Montréal
Timetable, Toronto time
16:06S9 290 from Chicago Midway at the gate
22:30AC 7164 to Montréal leaves the gate
6 h 24 apart on the timetable
The last days
S9 290 and AC 7164 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.