CA 1011 then UA 2101 at O'Hare
Anchorage → Chicago → Boston
Timetable, Chicago time
17:12CA 1011 from Anchorage at the gate
13:59UA 2101 to Boston leaves the gate
20 h 47 apart on the timetable, overnight
UA 2101 leaves 20 h 47 after CA 1011 arrives on the timetable: more than half a day, so not a connection we count.