BR 608 then UA 630 at O'Hare
Anchorage → Chicago → Madison
Timetable, Chicago time
20:40BR 608 from Anchorage at the gate
19:59UA 630 to Madison leaves the gate
23 h 19 apart on the timetable, overnight
UA 630 leaves 23 h 19 after BR 608 arrives on the timetable: more than half a day, so not a connection we count.