CI 5240 then AA 3960 at O'Hare
Anchorage → Chicago → Valparaiso
Timetable, Chicago time
15:04CI 5240 from Anchorage at the gate
08:34AA 3960 to Valparaiso leaves the gate
17 h 30 apart on the timetable, overnight
AA 3960 leaves 17 h 30 after CI 5240 arrives on the timetable: more than half a day, so not a connection we count.