Airlines with flights from Chicago to Portland
There are two airlines with scheduled flights between MDW and PDX. Southwest is the only airline with non-stop flights from Midway International Airport to Portland International and the flight time is 4 hours and 25 minutes.
There are two airlines with scheduled flights between MDW and PDX. Southwest is the only airline with non-stop flights from Midway International Airport to Portland International and the flight time is 4 hours and 25 minutes. Choose airline
Direct
Non-stop
4h 25min
Via Denver
5h 55min
Via Kansas City
6h 0min
Via Minneapolis
6h 5min
Via Sacramento
6h 30min
Via Salt Lake City
8h 25min
Via Indianapolis
8h 55min
Starts 06/06
Via Saint Louis
6h 5min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 4 hours and 25 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
23 flights per week
-
Boeing 737MAX 8 Passenger
MDW
Direct
PDX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2809
10:05
10:15
10:15
10:05
10:05
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10:00
WN3928
----
----
----
----
----
10:25
----
WN4765
16:40
17:35
17:35
16:40
16:40
----
----
WN2852
21:35
21:10
21:10
21:35
21:35
20:25
21:45
The timetable & schedule information was updated at 2026-04-21
Via Denver with Southwest Airlines
-
Total flight time: 5h 55m - 10h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
158 flights per week
-
Boeing 737MAX 8 Passenger
MDW
Via DEN
PDX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2989
WN300
WN300
05:15
05:30
05:30
05:15
05:15
05:25
----
WN2989
WN2736
WN2736
----
----
----
----
----
----
05:25
WN2765
WN1667
WN1667
06:45
----
----
06:45
06:45
----
----
WN1267
WN4271
WN4271
----
----
----
----
----
----
08:00
WN1866
WN4271
WN4271
----
----
----
----
----
----
08:50
WN1102
WN4271
WN4271
----
09:00
09:00
----
----
----
----
WN206
WN4271
WN4271
----
----
----
----
----
09:55
----
WN2733
WN4271
WN4271
----
----
----
----
----
----
10:10
WN2960
WN4026
WN4026
----
11:20
11:20
----
----
----
----
WN1331
WN1669
WN1669
----
----
----
----
----
12:50
----
WN4450
WN1669
WN1669
13:10
----
----
13:10
13:10
----
----
WN1893
WN1669
WN1669
13:15
----
----
13:15
13:15
----
----
WN2142
WN1669
WN1669
----
----
----
----
----
----
13:45
WN2768
WN290
WN290
----
----
----
----
----
14:15
----
WN2768
WN1682
WN1682
14:30
----
----
14:30
14:30
----
----
WN2766
WN4708
WN4708
----
14:45
14:45
----
----
----
----
WN2769
WN1669
WN1669
----
----
----
----
----
----
15:25
WN4450
WN1671
WN1671
----
----
----
----
----
----
15:30
WN2769
WN1670
WN1670
16:15
----
----
16:15
16:15
----
----
WN1893
WN1671
WN1671
----
----
----
----
----
----
16:35
WN2769
WN1671
WN1671
----
16:40
16:40
----
----
----
----
WN2769
WN4698
WN4698
----
----
----
----
----
16:50
----
WN2844
WN4698
WN4698
----
----
----
----
----
17:10
----
WN481
WN1671
WN1671
----
----
----
----
----
----
17:20
WN2675
WN1671
WN1671
----
18:00
18:00
----
----
----
----
WN1497
WN1671
WN1671
18:00
----
----
18:00
18:00
----
----
The timetable & schedule information was updated at 2026-04-21
Via Kansas City with Southwest Airlines
-
Total flight time: 6h 00m - 8h 30m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
4 flights per week
-
Boeing 737MAX 8 Passenger
MDW
Via MCI
PDX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2810
WN753
WN753
----
----
----
----
----
----
09:50
The timetable & schedule information was updated at 2026-04-21
Via Minneapolis with Delta Air Lines
-
Total flight time: 6h 05m - 8h 15m.
-
Sky Team Alliance
-
16 flights per week
MDW
Via MSP
PDX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
DL4713
DL2391
DL2391
19:16
19:16
19:16
19:16
19:16
----
19:16
The timetable & schedule information was updated at 2026-04-21
Via Sacramento with Southwest Airlines
-
Total flight time: 6h 30m - 10h 50m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
25 flights per week
-
Boeing 737MAX 8 Passenger
MDW
Via SMF
PDX
W25, Jun 15 - Jun 21
Flight
Mon
Jun 15
Tue
Jun 16
Wed
Jun 17
Thu
Jun 18
Fri
Jun 19
Sat
Jun 20
Sun
Jun 21
WN2094
WN422
WN422
10:20
----
----
10:20
10:20
----
----
WN1876
WN3813
WN3813
----
10:20
10:20
----
----
----
----
WN1524
WN432
WN432
----
17:45
17:45
----
----
----
----
The timetable & schedule information was updated at 2026-04-21
