BR 658 then WS 2558 at Toronto Pearson
Chicago O'Hare → Toronto → Cancún
Timetable, Toronto time
17:39BR 658 from Chicago O'Hare at the gate
16:35WS 2558 to Cancún leaves the gate
22 h 56 apart on the timetable, overnight
WS 2558 leaves 22 h 56 after BR 658 arrives on the timetable: more than half a day, so not a connection we count.