Airlines with flights from Chicago to Portland

There are two airlines with scheduled flights between MDW and PWM. Southwest is the only airline with non-stop flights from Midway International Airport to Portland International Jetport and the flight time is 2 hours and 10 minutes.

Choose airline

Schedules

Non-stop with Southwest Airlines

  • Total flight time: 2 hours and 10 minutes
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 7 flights per week
MDW
Direct
PWM

The timetable & schedule information was updated at 2024-10-16

Via Baltimore with Southwest Airlines

  • Total flight time: 4h 00m - 8h 35m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
  • 39 flights per week
MDW
 
Via BWI
 
PWM
 
Flight
Mon
Nov 4
Tue
Nov 5
Wed
Nov 6
Thu
Nov 7
Fri
Nov 8
Sat
Nov 9
Sun
Nov 10
WN281
WN805
----
----
----
----
----
06:40
----
WN1382
WN1356
07:20
07:20
07:20
----
----
----
----
WN4325
WN1947
----
----
----
08:15
08:15
----
08:15
WN1035
WN2438
10:05
10:00
10:05
----
----
----
----
WN1997
WN1544
----
----
----
12:35
12:35
----
12:35
WN2226
WN1733
----
----
----
----
----
13:15
----
WN6511
WN1733
15:20
----
----
----
----
----
----
WN3710
WN1733
17:30
17:25
17:30
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

The timetable & schedule information was updated at 2024-10-16

Via Detroit with Delta Air Lines

  • Total flight time: 4h 07m - 5h 57m.
  • Sky Team Alliance
  • 7 flights per week
MDW
 
Via DTW
 
PWM

The timetable & schedule information was updated at 2024-10-16

Via Nashville with Southwest Airlines

  • Total flight time: 6h 20m - 7h 05m.
  • Low-cost airline
  • Chicago is a Southwest Airlines focus city (Operating base).
MDW
 
Via BNA
 
PWM
 
Flight
Mon
Nov 4
Tue
Nov 5
Wed
Nov 6
Thu
Nov 7
Fri
Nov 8
Sat
Nov 9
Sun
Nov 10
WN281
WN805
----
----
----
----
----
06:40
----
WN1382
WN1356
07:20
07:20
07:20
----
----
----
----
WN4325
WN1947
----
----
----
08:15
08:15
----
08:15
WN1035
WN2438
10:05
10:00
10:05
----
----
----
----
WN1997
WN1544
----
----
----
12:35
12:35
----
12:35
WN2226
WN1733
----
----
----
----
----
13:15
----
WN6511
WN1733
15:20
----
----
----
----
----
----
WN3710
WN1733
17:30
17:25
17:30
----
----
----
----
SHOW RETURN SCHEDULE
CHECK PRICES FOR MDW - PWM

The timetable & schedule information was updated at 2024-10-16

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