UA 375 then CX 2095 at O'Hare
Boston → Chicago → Anchorage
Timetable, Chicago time
15:32UA 375 from Boston at the gate
10:00CX 2095 to Anchorage leaves the gate
18 h 28 apart on the timetable, overnight
CX 2095 leaves 18 h 28 after UA 375 arrives on the timetable: more than half a day, so not a connection we count.