CA 3103 then UA 4166 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
15:07CA 3103 from Anchorage at the gate
10:42UA 4166 to Madison leaves the gate
19 h 35 apart on the timetable, overnight
UA 4166 leaves 19 h 35 after CA 3103 arrives on the timetable: more than half a day, so not a connection we count.