Airlines with flights from Portland to Chicago
There are two 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 48 minutes.
There are two 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 48 minutes. Choose airline
Direct
Non-stop
3h 48min
Via Denver
5h 20min
Via Minneapolis
5h 32min
Via Sacramento
6h 0min
Via Detroit
7h 27min
NEW
Via Indianapolis
8h 15min
Starts 06/06
Via Kansas City
5h 25min
Starts 06/06
Via Saint Louis
5h 25min
Schedules
Non-stop with Southwest Airlines
-
Total flight time: 3 hours and 48 minutes
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
24 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Direct
MDW
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
WN130
----
----
----
----
----
----
05:10
WN1148
06:00
----
----
06:00
06:00
----
----
WN3669
----
06:00
06:00
----
----
----
----
WN3325
----
----
----
----
----
06:05
----
WN3202
11:50
11:15
11:15
11:50
11:50
----
----
WN3203
23:30
23:30
23:30
23:30
23:30
23:30
23:30
The timetable & schedule information was updated at 2026-04-21
Via Denver with Southwest Airlines
-
Total flight time: 5h 20m - 10h 00m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
171 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Via DEN
MDW
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
WN3195
WN755
WN755
05:50
05:35
05:35
05:50
05:50
05:15
05:50
WN4099
WN1539
WN1539
07:10
----
----
07:10
07:10
----
----
WN471
WN1524
WN1524
----
----
----
----
----
07:55
----
WN3693
WN1524
WN1524
----
----
----
----
----
----
08:30
WN3693
WN1603
WN1603
----
08:35
08:35
----
----
----
----
WN2146
WN1603
WN1603
----
----
----
----
----
----
10:10
WN1658
WN1251
WN1251
11:00
----
----
11:00
11:00
----
----
WN2519
WN223
WN223
----
----
----
----
----
14:10
----
WN2519
WN1614
WN1614
----
14:35
14:35
----
----
----
14:45
WN2519
WN1615
WN1615
14:45
----
----
14:45
14:45
----
----
The timetable & schedule information was updated at 2026-04-21
Via Minneapolis with Delta Air Lines
-
Total flight time: 5h 32m - 6h 36m.
-
Sky Team Alliance
-
28 flights per week
PDX
Via MSP
MDW
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
DL2359
DL4712
DL4712
00:31
00:31
00:31
00:31
00:31
00:31
----
The timetable & schedule information was updated at 2026-04-21
Via Sacramento with Southwest Airlines
-
Total flight time: 6h 00m - 9h 55m.
-
Low-cost airline
-
Chicago is a Southwest Airlines focus city (Operating base).
-
30 flights per week
-
Boeing 737-800 (winglets) Passenger/BBJ2Boeing 737MAX 8 Passenger
PDX
Via SMF
MDW
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
WN3211
WN3769
WN3769
----
05:25
05:25
----
----
----
----
WN300
WN3769
WN3769
10:00
----
----
10:00
10:00
----
----
WN3213
WN3802
WN3802
20:15
19:50
19:50
20:15
20:15
----
----
WN423
WN3802
WN3802
----
----
----
----
----
20:20
----
WN902
WN3802
WN3802
----
----
----
----
----
----
21:45
The timetable & schedule information was updated at 2026-04-21
Via Detroit with Delta Air Lines
-
Total flight time: 7h 27m - 8h 02m.
-
Sky Team Alliance
-
32 flights per week
PDX
Via DTW
MDW
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
DL919
DL4684
DL4684
23:15
----
----
23:15
23:15
----
23:15
The timetable & schedule information was updated at 2026-04-21
