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
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).
-
19 flights per week
-
Boeing 737MAX 8 Passenger
MDW
Direct
PDX
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2809
10:05
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WN4246
----
10:20
10:20
18:30
18:30
10:15
10:25
WN806
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20:55
20:55
10:40
10:40
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WN4765
16:40
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WN4840
----
----
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20:50
20:50
18:00
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WN265
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21:20
WN2852
21:35
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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
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2989
WN300
WN300
05:15
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WN2717
WN1601
WN1601
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06:40
06:40
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----
----
06:30
WN2765
WN1667
WN1667
06:45
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----
----
----
----
----
WN2717
WN449
WN449
----
----
----
----
----
06:50
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WN136
WN1603
WN1603
----
----
----
----
----
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07:55
WN199
WN874
WN874
----
08:20
08:20
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WN400
WN1603
WN1603
----
----
----
----
----
----
09:30
WN271
WN1603
WN1603
----
----
----
----
----
10:00
----
WN3539
WN1161
WN1161
----
10:05
10:05
----
----
----
----
WN271
WN874
WN874
----
10:05
10:05
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----
----
----
WN4571
WN3142
WN3142
----
----
----
----
----
----
10:10
WN1148
WN1161
WN1161
----
11:10
11:10
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----
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----
WN2719
WN2045
WN2045
----
12:00
12:00
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----
----
----
WN2719
WN1601
WN1601
----
----
----
12:15
12:15
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WN2719
WN3142
WN3142
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----
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----
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12:25
WN4450
WN1669
WN1669
13:10
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----
----
----
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WN1893
WN1669
WN1669
13:15
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WN2718
WN3142
WN3142
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13:40
WN102
WN1161
WN1161
----
----
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14:05
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WN1271
WN874
WN874
----
----
----
----
----
14:15
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WN2768
WN1682
WN1682
14:30
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WN267
WN874
WN874
----
----
----
----
----
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14:40
WN2769
WN1670
WN1670
16:15
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WN655
WN1534
WN1534
----
----
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16:25
16:25
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WN2721
WN1615
WN1615
----
18:00
18:00
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----
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16:45
WN163
WN1303
WN1303
----
----
----
17:00
17:00
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WN2721
WN874
WN874
----
----
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----
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17:05
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WN1497
WN1671
WN1671
18:00
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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
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN615
WN4639
WN4639
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10:30
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WN704
WN2422
WN2422
----
----
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15:35
WN984
WN2422
WN2422
----
----
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17:35
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
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
DL4713
DL2391
DL2391
19:06
19:06
19:06
19:06
19:06
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19:06
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
W32, Aug 03 - Aug 09
Flight
Mon
Aug 3
Tue
Aug 4
Wed
Aug 5
Thu
Aug 6
Fri
Aug 7
Sat
Aug 8
Sun
Aug 9
WN2815
WN2513
WN2513
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06:10
WN4713
WN198
WN198
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10:05
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WN4713
WN2761
WN2761
----
10:10
10:10
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WN2094
WN422
WN422
10:20
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The timetable & schedule information was updated at 2026-04-21
