DL 5404 then CI 5301 at JFK
Milwaukee → New York → Toronto
Timetable, New York time
11:28DL 5404 from Milwaukee at the gate
09:05CI 5301 to Toronto leaves the gate
21 h 37 apart on the timetable, overnight
CI 5301 leaves 21 h 37 after DL 5404 arrives on the timetable: more than half a day, so not a connection we count.