CV 12 then UA 5530 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
19:11CV 12 from Anchorage at the gate
13:59UA 5530 to Madison leaves the gate
18 h 48 apart on the timetable, overnight
UA 5530 leaves 18 h 48 after CV 12 arrives on the timetable: more than half a day, so not a connection we count.