Airlines with flights from Portland to Chicago
There are three airlines with scheduled flights between PDX and MDW. Southwest is the only airline with non-stop flights from Portland International to Midway International Airport and the flight time is 3 hours and 55 minutes.
There are three airlines with scheduled flights between PDX and MDW. Southwest is the only airline with non-stop flights from Portland International to Midway International Airport and the flight time is 3 hours and 55 minutes. Choose airline
Non-stop
3h 55min
Via Denver
6h 45min
Via Minneapolis
6h 7min
Via Sacramento
7h 50min
Via Denver
7h 19min
Starts 14/04
Via Detroit
7h 47min
Starts 07/06
Via Saint Louis
5h 48min
Starts 07/06
Via Kansas City
6h 10min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 3 hours and 55 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
10 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Direct
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN3049
06:35
08:00
09:00
08:00
06:35
06:25
06:35
The timetable & schedule information was updated at 2025-01-15
Via Denver with Southwest Airlines
-
Total flight time: 5h 25m - 9h 10m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
15 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Via DEN
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN681
WN1722
WN1722
----
----
----
----
----
05:00
----
WN681
WN258
WN258
----
----
----
----
----
05:00
----
WN133
WN553
WN553
----
05:00
----
05:00
----
----
----
WN133
WN2337
WN2337
----
----
06:50
----
----
----
----
WN133
WN2756
WN2756
----
----
06:50
----
----
----
----
WN133
WN4876
WN4876
----
----
06:50
----
----
----
----
WN2361
WN999
WN999
06:55
----
----
----
06:55
----
06:55
WN4221
WN5303
WN5303
----
----
07:45
----
----
----
----
WN1816
WN4514
WN4514
08:55
----
----
----
08:55
----
08:55
WN1816
WN805
WN805
08:55
----
----
----
08:55
----
08:55
WN777
WN4514
WN4514
----
09:00
----
09:00
----
----
----
WN133
WN4514
WN4514
----
----
----
----
----
09:10
----
WN133
WN1325
WN1325
----
----
----
----
----
09:10
----
WN2078
WN340
WN340
----
----
13:10
----
----
----
----
WN2078
WN4156
WN4156
----
----
----
----
----
13:40
----
WN2078
WN898
WN898
----
----
----
----
----
13:40
----
The timetable & schedule information was updated at 2025-01-15
Via Minneapolis with Delta Air Lines
-
Total flight time: 5h 45m - 7h 51m.
-
Sky Team Alliance
-
6 flights per week
PDX
Via MSP
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
DL2359
DL3778
DL3778
----
00:59
00:59
00:59
00:59
00:59
----
The timetable & schedule information was updated at 2025-01-15
Via Sacramento with Southwest Airlines
-
Total flight time: 6h 00m - 10h 25m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
5 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Via SMF
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
WN681
WN1722
WN1722
----
----
----
----
----
05:00
----
WN681
WN258
WN258
----
----
----
----
----
05:00
----
WN133
WN553
WN553
----
05:00
----
05:00
----
----
----
WN133
WN2337
WN2337
----
----
06:50
----
----
----
----
WN133
WN2756
WN2756
----
----
06:50
----
----
----
----
WN133
WN4876
WN4876
----
----
06:50
----
----
----
----
WN2361
WN999
WN999
06:55
----
----
----
06:55
----
06:55
WN4221
WN5303
WN5303
----
----
07:45
----
----
----
----
WN1816
WN4514
WN4514
08:55
----
----
----
08:55
----
08:55
WN1816
WN805
WN805
08:55
----
----
----
08:55
----
08:55
WN777
WN4514
WN4514
----
09:00
----
09:00
----
----
----
WN133
WN4514
WN4514
----
----
----
----
----
09:10
----
WN133
WN1325
WN1325
----
----
----
----
----
09:10
----
WN2078
WN340
WN340
----
----
13:10
----
----
----
----
WN2078
WN4156
WN4156
----
----
----
----
----
13:40
----
WN2078
WN898
WN898
----
----
----
----
----
13:40
----
The timetable & schedule information was updated at 2025-01-15
Via Denver with Frontier Airlines
-
Total flight time: 5h 35m - 7h 47m.
-
Low-cost airline
-
Chicago is a Frontier Airlines focus city.
-
3 flights per week
PDX
Via DEN
MDW
W8, Feb 17 - Feb 23
Flight
Mon
Feb 17
Tue
Feb 18
Wed
Feb 19
Thu
Feb 20
Fri
Feb 21
Sat
Feb 22
Sun
Feb 23
Sorry. We could not find any flights for this week.
The timetable & schedule information was updated at 2025-01-15
