UA 3911 then AA 4384 at O'Hare
Portland (Oregon) → Chicago → Pensacola
Timetable, Chicago time
17:09UA 3911 from Portland (Oregon) at the gate
11:32AA 4384 to Pensacola leaves the gate
18 h 23 apart on the timetable, overnight
AA 4384 leaves 18 h 23 after UA 3911 arrives on the timetable: more than half a day, so not a connection we count.