Airlines with flights from Portland to Chicago
There are two airlines with scheduled flights between PWM and MDW. Southwest is the only airline with non-stop flights from Portland International Jetport to Midway International Airport and the flight time is 2 hours and 35 minutes.
Choose airline
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 2 hours and 35 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
1 flight per week
PWM
Direct
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
The next flight with this airline is scheduled on 2025-06-05.
The timetable & schedule information was updated at 2024-12-13
Via Baltimore with Southwest Airlines
-
Total flight time: 4h 20m - 8h 25m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
17 flights per week
PWM
Via BWI
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
The next flight with this airline is scheduled on 2025-06-05.
The timetable & schedule information was updated at 2024-12-13
Via Detroit with Delta Air Lines
-
Total flight time: 4h 25m - 5h 25m.
-
Sky Team Alliance
-
7 flights per week
PWM
Via DTW
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13
Via Nashville with Southwest Airlines
-
Total flight time: 5h 45m - 8h 40m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
3 flights per week
PWM
Via BNA
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
The next flight with this airline is scheduled on 2025-06-05.
The timetable & schedule information was updated at 2024-12-13
Via Minneapolis with Delta Air Lines
-
Total flight time: 7h 25m - 7h 39m.
-
Sky Team Alliance
PWM
Via MSP
MDW
W1, Dec 30 - Jan 05
Flight
Mon
Jan 1
Tue
Jan 2
Wed
Jan 3
Thu
Jan 4
Fri
Jan 5
Sat
Jan 6
Sun
Jan 7
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2024-12-13