All airlines flying from Chicago Midway (MDW) to Portland (PDX).

FLIGHT SCHEDULE
Direct Flights:
Mon,Thu,Fri 12:05 Chicago Midway (MDW) 14:30 Portland (PDX) Southwest Airlines WN 236 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 12:05 Chicago Midway (MDW) 14:30 Portland (PDX) Southwest Airlines WN 236 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-20 through 2026-03-01
Sat 14:15 Chicago Midway (MDW) 16:45 Portland (PDX) Southwest Airlines WN 519 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Operates only on 2026-01-03
Mon,Thu,Fri 10:40 Chicago Midway (MDW) 12:50 Portland (PDX) Southwest Airlines WN 806 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-06 through 2026-09-28
Tue,Wed 20:35 Chicago Midway (MDW) 22:50 Portland (PDX) Southwest Airlines WN 806 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-04 through 2026-09-30
Sun 21:20 Chicago Midway (MDW) 23:30 Portland (PDX) Southwest Airlines WN 806 Non-stop Boeing 737 MAX 8 (7M8) 4:10 Effective 2026-08-09 through 2026-09-27
Sun 10:00 Chicago Midway (MDW) 12:20 Portland (PDX) Southwest Airlines WN 1651 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-12 through 2026-05-17
Sun 10:00 Chicago Midway (MDW) 12:20 Portland (PDX) Southwest Airlines WN 1651 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Operates only on 2026-05-31
Mon-Fri 15:35 Chicago Midway (MDW) 18:00 Portland (PDX) Southwest Airlines WN 1691 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 15:35 Chicago Midway (MDW) 18:00 Portland (PDX) Southwest Airlines WN 1691 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-01-18 through 2026-01-23
Mon-Fri 15:35 Chicago Midway (MDW) 18:00 Portland (PDX) Southwest Airlines WN 1691 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 15:35 Chicago Midway (MDW) 18:00 Portland (PDX) Southwest Airlines WN 1691 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-08 through 2026-02-11
Tue,Wed 15:35 Chicago Midway (MDW) 18:00 Portland (PDX) Southwest Airlines WN 1691 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-01-11 through 2026-01-16
Mon,Sun 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-02-01 through 2026-02-06
Mon,Sun 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2026-02-17 through 2026-02-23
Mon 08:10 Chicago Midway (MDW) 10:45 Portland (PDX) Southwest Airlines WN 2029 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Operates only on 2026-03-02
Wed,Thu 16:50 Chicago Midway (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Valid until 2026-01-01
Mon,Tue,Fri,Sun 19:30 Chicago Midway (MDW) 22:00 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Valid until 2026-01-04
Mon 21:50 Chicago Midway (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737-800 (73H) 4:30 Operates only on 2026-01-05 The flight arrives 1 day after departure.
Sat 08:35 Chicago Midway (MDW) 11:15 Portland (PDX) Southwest Airlines WN 2406 Non-stop Boeing 737-700 (Scimitar Winglets) 4:40 Effective 2026-01-10 through 2026-02-07
Mon,Thu,Fri 10:15 Chicago Midway (MDW) 12:35 Portland (PDX) Southwest Airlines WN 2497 Non-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2026-04-09 through 2026-06-01
Sat 10:15 Chicago Midway (MDW) 12:35 Portland (PDX) Southwest Airlines WN 2497 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-11 through 2026-05-30
Tue,Wed 20:50 Chicago Midway (MDW) 23:10 Portland (PDX) Southwest Airlines WN 2497 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-07 through 2026-06-03
Sun 10:00 Chicago Midway (MDW) 12:20 Portland (PDX) Southwest Airlines WN 2809 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 10:05 Chicago Midway (MDW) 12:25 Portland (PDX) Southwest Airlines WN 2809 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-04 through 2026-08-03
Tue,Wed 10:15 Chicago Midway (MDW) 12:30 Portland (PDX) Southwest Airlines WN 2809 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-06-09 through 2026-07-29
Sat 20:25 Chicago Midway (MDW) 22:45 Portland (PDX) Southwest Airlines WN 2852 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-06 through 2026-08-01
Tue,Wed 21:10 Chicago Midway (MDW) 23:30 Portland (PDX) Southwest Airlines WN 2852 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 21:35 Chicago Midway (MDW) 23:55 Portland (PDX) Southwest Airlines WN 2852 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-04 through 2026-08-03
Sun 21:45 Chicago Midway (MDW) 00:05 Portland (PDX) Southwest Airlines WN 2852 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-07 through 2026-08-02 The flight arrives 1 day after departure.
Sat 20:30 Chicago Midway (MDW) 23:00 Portland (PDX) Southwest Airlines WN 2905 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2026-02-14 through 2026-02-28
Tue,Wed 10:10 Chicago Midway (MDW) 12:30 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-07 through 2026-06-03
Sat 18:05 Chicago Midway (MDW) 20:25 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-11 through 2026-05-30
Sun 20:35 Chicago Midway (MDW) 22:55 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Operates only on 2026-05-24
Sun 21:45 Chicago Midway (MDW) 00:05 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-12 through 2026-05-17 The flight arrives 1 day after departure.
Sun 21:45 Chicago Midway (MDW) 00:05 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Operates only on 2026-05-31 The flight arrives 1 day after departure.
Mon,Thu,Fri 21:50 Chicago Midway (MDW) 00:10 Portland (PDX) Southwest Airlines WN 3579 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-04-09 through 2026-06-01 The flight arrives 1 day after departure.
Sat 10:15 Chicago Midway (MDW) 12:30 Portland (PDX) Southwest Airlines WN 3928 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-06-06 through 2026-08-01
Sun 10:05 Chicago Midway (MDW) 12:30 Portland (PDX) Southwest Airlines WN 3975 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-08 through 2026-04-05
Mon-Fri 10:30 Chicago Midway (MDW) 12:50 Portland (PDX) Southwest Airlines WN 3975 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-03-05 through 2026-04-06
Sat 11:00 Chicago Midway (MDW) 13:20 Portland (PDX) Southwest Airlines WN 3975 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-03-07 through 2026-04-04
Tue,Wed 20:45 Chicago Midway (MDW) 23:10 Portland (PDX) Southwest Airlines WN 3976 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-10 through 2026-04-01
Sun 21:40 Chicago Midway (MDW) 00:05 Portland (PDX) Southwest Airlines WN 3976 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-08 through 2026-04-05 The flight arrives 1 day after departure.
Mon,Thu,Fri 22:20 Chicago Midway (MDW) 00:45 Portland (PDX) Southwest Airlines WN 3976 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-05 through 2026-04-06 The flight arrives 1 day after departure.
Sat 22:30 Chicago Midway (MDW) 00:55 Portland (PDX) Southwest Airlines WN 3976 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2026-03-14 through 2026-04-04 The flight arrives 1 day after departure.
Sat 10:15 Chicago Midway (MDW) 12:30 Portland (PDX) Southwest Airlines WN 4246 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-08 through 2026-09-26
Tue,Wed 10:20 Chicago Midway (MDW) 12:35 Portland (PDX) Southwest Airlines WN 4246 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-04 through 2026-09-30

1 2

A domestic route departing from the Chicago Midway airport (MDW) and arriving at Portland airport (PDX).
The flight distance is 1745 miles, or 2809 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 4:10 and 4:40.

Return (PDX-MDW) flights

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All airlines flying from Chicago Midway (MDW) to Portland (PDX).

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN236

12:05

Chicago Midway (MDW)

14:30

Portland (PDX)

Effective 2026-02-12 through 2026-02-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN236

12:05

Chicago Midway (MDW)

14:30

Portland (PDX)

Effective 2026-02-20 through 2026-03-01

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN519

14:15

Chicago Midway (MDW)

16:45

Portland (PDX)

Operates only on 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:30, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN806

10:40

Chicago Midway (MDW)

12:50

Portland (PDX)

Effective 2026-08-06 through 2026-09-28

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN806

20:35

Chicago Midway (MDW)

22:50

Portland (PDX)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN806

21:20

Chicago Midway (MDW)

23:30

Portland (PDX)

Effective 2026-08-09 through 2026-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:10, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1651

10:00

Chicago Midway (MDW)

12:20

Portland (PDX)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1651

10:00

Chicago Midway (MDW)

12:20

Portland (PDX)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1691

15:35

Chicago Midway (MDW)

18:00

Portland (PDX)

Effective 2026-01-06 through 2026-01-14

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1691

15:35

Chicago Midway (MDW)

18:00

Portland (PDX)

Effective 2026-01-18 through 2026-01-23

Mon
-

Tue

Wed

Thu

Fri

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1691

15:35

Chicago Midway (MDW)

18:00

Portland (PDX)

Effective 2026-01-26 through 2026-02-04

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1691

15:35

Chicago Midway (MDW)

18:00

Portland (PDX)

Effective 2026-02-08 through 2026-02-11

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN1691

15:35

Chicago Midway (MDW)

18:00

Portland (PDX)

Effective 2026-02-18 through 2026-03-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Effective 2026-01-11 through 2026-01-16

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Effective 2026-01-19 through 2026-01-25

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Effective 2026-02-01 through 2026-02-06

Mon
-

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Effective 2026-02-09 through 2026-02-15

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Effective 2026-02-17 through 2026-02-23

Mon

Tue

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2029

08:10

Chicago Midway (MDW)

10:45

Portland (PDX)

Operates only on 2026-03-02

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:35, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2039

16:50

Chicago Midway (MDW)

19:20

Portland (PDX)

Valid until 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2039

19:30

Chicago Midway (MDW)

22:00

Portland (PDX)

Valid until 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2039

21:50

Chicago Midway (MDW)

00:20(+1)

Portland (PDX)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN2406

08:35

Chicago Midway (MDW)

11:15

Portland (PDX)

Effective 2026-01-10 through 2026-02-07

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:40, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2497

10:15

Chicago Midway (MDW)

12:35

Portland (PDX)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Southwest Airlines WN2497

10:15

Chicago Midway (MDW)

12:35

Portland (PDX)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2497

20:50

Chicago Midway (MDW)

23:10

Portland (PDX)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2809

10:00

Chicago Midway (MDW)

12:20

Portland (PDX)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2809

10:05

Chicago Midway (MDW)

12:25

Portland (PDX)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2809

10:15

Chicago Midway (MDW)

12:30

Portland (PDX)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2852

20:25

Chicago Midway (MDW)

22:45

Portland (PDX)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2852

21:10

Chicago Midway (MDW)

23:30

Portland (PDX)

Effective 2026-06-09 through 2026-07-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2852

21:35

Chicago Midway (MDW)

23:55

Portland (PDX)

Effective 2026-06-04 through 2026-08-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN2852

21:45

Chicago Midway (MDW)

00:05(+1)

Portland (PDX)

Effective 2026-06-07 through 2026-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN2905

20:30

Chicago Midway (MDW)

23:00

Portland (PDX)

Effective 2026-02-14 through 2026-02-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3579

10:10

Chicago Midway (MDW)

12:30

Portland (PDX)

Effective 2026-04-07 through 2026-06-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3579

18:05

Chicago Midway (MDW)

20:25

Portland (PDX)

Effective 2026-04-11 through 2026-05-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3579

20:35

Chicago Midway (MDW)

22:55

Portland (PDX)

Operates only on 2026-05-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3579

21:45

Chicago Midway (MDW)

00:05(+1)

Portland (PDX)

Effective 2026-04-12 through 2026-05-17

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3579

21:45

Chicago Midway (MDW)

00:05(+1)

Portland (PDX)

Operates only on 2026-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3579

21:50

Chicago Midway (MDW)

00:10(+1)

Portland (PDX)

Effective 2026-04-09 through 2026-06-01

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3928

10:15

Chicago Midway (MDW)

12:30

Portland (PDX)

Effective 2026-06-06 through 2026-08-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3975

10:05

Chicago Midway (MDW)

12:30

Portland (PDX)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3975

10:30

Chicago Midway (MDW)

12:50

Portland (PDX)

Effective 2026-03-05 through 2026-04-06

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3975

11:00

Chicago Midway (MDW)

13:20

Portland (PDX)

Effective 2026-03-07 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3976

20:45

Chicago Midway (MDW)

23:10

Portland (PDX)

Effective 2026-03-10 through 2026-04-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN3976

21:40

Chicago Midway (MDW)

00:05(+1)

Portland (PDX)

Effective 2026-03-08 through 2026-04-05

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3976

22:20

Chicago Midway (MDW)

00:45(+1)

Portland (PDX)

Effective 2026-03-05 through 2026-04-06

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN3976

22:30

Chicago Midway (MDW)

00:55(+1)

Portland (PDX)

Effective 2026-03-14 through 2026-04-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:25, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Southwest Airlines WN4246

10:15

Chicago Midway (MDW)

12:30

Portland (PDX)

Effective 2026-08-08 through 2026-09-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Southwest Airlines WN4246

10:20

Chicago Midway (MDW)

12:35

Portland (PDX)

Effective 2026-08-04 through 2026-09-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)

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A domestic route departing from the Chicago Midway airport (MDW) and arriving at Portland airport (PDX).
The flight distance is 1745 miles, or 2809 km.
The timezone of the departure airport is UTC-6 , and the timezone of the arrival airport is UTC-8 . Current time at the point of departure is (loading...), and (loading...) at the point of arrival. There is a (loading...) hour time difference between the airports.
For direct flights, the flight time varies between 4:10 and 4:40.

Return (PDX-MDW) flights

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