BR 608 then UA 5748 at O'Hare
Anchorage → Chicago → Traverse City
Timetable, Chicago time
20:40BR 608 from Anchorage at the gate
11:20UA 5748 to Traverse City leaves the gate
14 h 40 apart on the timetable, overnight
UA 5748 leaves 14 h 40 after BR 608 arrives on the timetable: more than half a day, so not a connection we count.