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Flights
Portland Oregon - Chicago Midway (CHI)

Here is the updated flight timetable for Portland Oregon - 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 Boeing 737-800
Departure
05:00
Flight time: 3 h 55 min
Arrival
10:55
Southwest Airlines Boeing 737
Departure
05:00
Flight time: 4 h 55 min
Arrival
10:55
Southwest Airlines Boeing 737-700
Departure
05:50
Flight time: 3 h 55 min
Arrival
11:45
Southwest Airlines Boeing 737
Departure
05:50
Flight time: 3 h 55 min
Arrival
11:45
Southwest Airlines Boeing 737
Departure
06:00
Flight time: 4 h 0 min
Arrival
12:00
Southwest Airlines Boeing 737
Departure
06:00
Flight time: 4 h 55 min
Arrival
11:55
Southwest Airlines Boeing 737
Departure
06:00
Flight time: 4 h 55 min
Arrival
11:55
Southwest Airlines Boeing 737-800
Departure
06:00
Flight time: 3 h 55 min
Arrival
11:55
Southwest Airlines Boeing 737-800
Departure
06:00
Flight time: 4 h 0 min
Arrival
12:00
Southwest Airlines Boeing 737
Departure
06:05
Flight time: 4 h 0 min
Arrival
12:05
Southwest Airlines Boeing 737-800
Departure
06:05
Flight time: 3 h 55 min
Arrival
12:00
Southwest Airlines Boeing 737-700
Departure
06:10
Flight time: 4 h 0 min
Arrival
12:10
Southwest Airlines Boeing 737
Departure
06:10
Flight time: 3 h 55 min
Arrival
12:05
Southwest Airlines Boeing 737
Departure
06:15
Flight time: 4 h 55 min
Arrival
12:10
Southwest Airlines Boeing 737
Departure
06:20
Flight time: 3 h 55 min
Arrival
12:15
Southwest Airlines Boeing 737
Departure
06:30
Flight time: 4 h 55 min
Arrival
12:25
Southwest Airlines Boeing 737-800
Departure
06:30
Flight time: 4 h 55 min
Arrival
12:25
Southwest Airlines Boeing 737
Departure
06:30
Flight time: 4 h 55 min
Arrival
12:25
Southwest Airlines Boeing 737-800
Departure
06:45
Flight time: 4 h 55 min
Arrival
12:40
Southwest Airlines Boeing 737
Departure
06:55
Flight time: 4 h 0 min
Arrival
12:55
Southwest Airlines Boeing 737
Departure
07:00
Flight time: 6 h 30 min
Arrival
15:30
Southwest Airlines Boeing 737-700
Departure
07:20
Flight time: 3 h 55 min
Arrival
13:15
Southwest Airlines Boeing 737-800
Departure
07:45
Flight time: 4 h 55 min
Arrival
13:40
Southwest Airlines Boeing 737-700
Departure
08:15
Flight time: 3 h 55 min
Arrival
14:10
Southwest Airlines Boeing 737-700
Departure
08:30
Flight time: 3 h 55 min
Arrival
14:25
Southwest Airlines Boeing 737-700
Departure
08:30
Flight time: 10 h 45 min
Arrival
21:15
Southwest Airlines Boeing 737-700
Departure
08:55
Flight time: 3 h 55 min
Arrival
14:50
Southwest Airlines Boeing 737-700
Departure
09:20
Flight time: 3 h 55 min
Arrival
15:15
Southwest Airlines Boeing 737-700
Departure
09:20
Flight time: 3 h 55 min
Arrival
15:15
Southwest Airlines
Departure
10:20
Flight time: 4 h 55 min
Arrival
16:15
Southwest Airlines Boeing 737
Departure
10:35
Flight time: 6 h 35 min
Arrival
19:10
Southwest Airlines Boeing 737-800
Departure
10:35
Flight time: 4 h 0 min
Arrival
16:35
Southwest Airlines Boeing 737-800
Departure
10:50
Flight time: 3 h 50 min
Arrival
16:40
Southwest Airlines Boeing 737-700
Departure
13:20
Flight time: 3 h 55 min
Arrival
19:15
Southwest Airlines Boeing 737
Departure
13:25
Flight time: 3 h 55 min
Arrival
19:20
Southwest Airlines Boeing 737
Departure
13:30
Flight time: 4 h 0 min
Arrival
19:30
Southwest Airlines Boeing 737
Departure
13:35
Flight time: 4 h 0 min
Arrival
19:35
Southwest Airlines Boeing 737
Departure
13:50
Flight time: 3 h 55 min
Arrival
19:45
Southwest Airlines Boeing 737-800
Departure
13:55
Flight time: 3 h 55 min
Arrival
19:50
Southwest Airlines Boeing 737-700
Departure
14:30
Flight time: 3 h 55 min
Arrival
20:25
Southwest Airlines Boeing 737
Departure
14:30
Flight time: 3 h 55 min
Arrival
20:25
Southwest Airlines Boeing 737-800
Departure
14:35
Flight time: 3 h 50 min
Arrival
20:25