CV 251 then UA 4166 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
19:00CV 251 from Anchorage at the gate
10:42UA 4166 to Madison leaves the gate
15 h 42 apart on the timetable, overnight
UA 4166 leaves 15 h 42 after CV 251 arrives on the timetable: more than half a day, so not a connection we count.