UA 5360 then BR 643 at O'Hare
Charlottesville → Chicago → Anchorage
Timetable, Chicago time
15:19UA 5360 from Charlottesville at the gate
14:50BR 643 to Anchorage leaves the gate
23 h 31 apart on the timetable, overnight
BR 643 leaves 23 h 31 after UA 5360 arrives on the timetable: more than half a day, so not a connection we count.