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Portland Man - Chicago Midway (CHI)

Here is the updated flight timetable for Portland Man - Chicago Midway (CHI) for 2025. Click on your desired route or flight to see detailed timetables and additional information.

The timetable shows local time!

Southwest Airlines
Departure
07:40
Flight time: 2 h 35 min
Arrival
09:15
Southwest Airlines
Departure
10:25
Flight time: 2 h 35 min
Arrival
12:00
Southwest Airlines Boeing 737-700
Departure
10:30
Flight time: 2 h 30 min
Arrival
12:00
Southwest Airlines Boeing 737-700
Departure
10:30
Flight time: 4 h 15 min
Arrival
13:45
Southwest Airlines Boeing 737-800
Departure
10:35
Flight time: 2 h 30 min
Arrival
12:05
Southwest Airlines
Departure
14:40
Flight time: 2 h 35 min
Arrival
16:15
Southwest Airlines Boeing 737-800
Departure
16:00
Flight time: 2 h 35 min
Arrival
17:35
Southwest Airlines
Departure
16:45
Flight time: 2 h 35 min
Arrival
18:20
Southwest Airlines Boeing 737-800
Departure
16:50
Flight time: 2 h 35 min
Arrival
18:25
Southwest Airlines Boeing 737-700
Departure
16:55
Flight time: 2 h 35 min
Arrival
18:30
Southwest Airlines
Departure
17:25
Flight time: 4 h 15 min
Arrival
20:40
Southwest Airlines Boeing 737
Departure
17:50
Flight time: 2 h 35 min
Arrival
19:25
Southwest Airlines Boeing 737-700
Departure
18:55
Flight time: 2 h 35 min
Arrival
20:30
Southwest Airlines Boeing 737
Departure
18:55
Flight time: 2 h 35 min
Arrival
20:30
Southwest Airlines Boeing 737-800
Departure
19:10
Flight time: 2 h 35 min
Arrival
20:45
Southwest Airlines Boeing 737-700
Departure
19:40
Flight time: 2 h 35 min
Arrival
21:15
Southwest Airlines Boeing 737-700
Departure
19:55
Flight time: 2 h 35 min
Arrival
21:30
Southwest Airlines Boeing 737-800
Departure
19:55
Flight time: 2 h 35 min
Arrival
21:30