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

FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 13:25 Portland (PDX) 19:20 Midway, Chicago (MDW) Southwest Airlines WN 298 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-10-07 through 2025-10-29
Mon,Thu,Fri 05:30 Portland (PDX) 11:30 Midway, Chicago (MDW) Southwest Airlines WN 407 Non-stop Boeing 737-700 (73W) 4:00 Valid until 2025-06-02
Sun 06:00 Portland (PDX) 12:00 Midway, Chicago (MDW) Southwest Airlines WN 407 Non-stop Boeing 737-700 (73W) 4:00 Valid until 2025-05-18
Sun 06:00 Portland (PDX) 12:00 Midway, Chicago (MDW) Southwest Airlines WN 407 Non-stop Boeing 737-700 (73W) 4:00 Operates only on 2025-06-01
Tue,Wed 06:15 Portland (PDX) 12:15 Midway, Chicago (MDW) Southwest Airlines WN 407 Non-stop Boeing 737-700 (73W) 4:00 Valid until 2025-06-04
Sat 06:45 Portland (PDX) 12:45 Midway, Chicago (MDW) Southwest Airlines WN 407 Non-stop Boeing 737-800 (73H) 4:00 Valid until 2025-05-31
Fri 10:50 Portland (PDX) 16:40 Midway, Chicago (MDW) Southwest Airlines WN 914 Non-stop Boeing 737-800 (73H) 3:50 Operates only on 2025-07-04
Thu 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 1098 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-11-27
Mon,Thu,Fri 14:35 Portland (PDX) 20:25 Midway, Chicago (MDW) Southwest Airlines WN 1603 Non-stop Boeing 737-800 (73H) 3:50 Effective 2025-10-02 through 2025-10-31
Sat 10:35 Portland (PDX) 16:35 Midway, Chicago (MDW) Southwest Airlines WN 2149 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 13:35 Portland (PDX) 19:35 Midway, Chicago (MDW) Southwest Airlines WN 2149 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-07 through 2025-09-29
Sun 13:20 Portland (PDX) 19:15 Midway, Chicago (MDW) Southwest Airlines WN 2248 Non-stop Boeing 737-700 (73W) 3:55 Operates only on 2025-08-31
Sun 13:50 Portland (PDX) 19:45 Midway, Chicago (MDW) Southwest Airlines WN 2248 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-08-10 through 2025-08-24
Sun 13:50 Portland (PDX) 19:45 Midway, Chicago (MDW) Southwest Airlines WN 2248 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-09-07 through 2025-09-28
Tue,Wed,Sun 06:05 Portland (PDX) 12:00 Midway, Chicago (MDW) Southwest Airlines WN 2321 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-06-08 through 2025-08-03
Tue,Wed 09:20 Portland (PDX) 15:15 Midway, Chicago (MDW) Southwest Airlines WN 2668 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-08-05 through 2025-10-01
Tue,Wed 06:00 Portland (PDX) 12:00 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-05 through 2025-10-01
Sat 06:00 Portland (PDX) 12:00 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-09 through 2025-09-27
Sun 06:05 Portland (PDX) 12:05 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-10 through 2025-08-24
Sun 06:05 Portland (PDX) 12:05 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-09-07 through 2025-09-28
Mon,Thu,Fri 06:10 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737-800 (73H) 4:00 Effective 2025-08-07 through 2025-09-29
Sun 06:55 Portland (PDX) 12:55 Midway, Chicago (MDW) Southwest Airlines WN 2678 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Operates only on 2025-08-31
Mon,Thu,Fri 05:50 Portland (PDX) 11:45 Midway, Chicago (MDW) Southwest Airlines WN 2735 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 05:50 Portland (PDX) 11:45 Midway, Chicago (MDW) Southwest Airlines WN 2735 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-07-07 through 2025-08-04
Sat 06:20 Portland (PDX) 12:15 Midway, Chicago (MDW) Southwest Airlines WN 2735 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-06-07 through 2025-08-02
Tue,Wed 08:55 Portland (PDX) 14:50 Midway, Chicago (MDW) Southwest Airlines WN 2735 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-06-10 through 2025-07-30
Sun 12:30 Portland (PDX) 18:25 Midway, Chicago (MDW) Southwest Airlines WN 2927 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-05-25
Tue,Wed 13:30 Portland (PDX) 19:30 Midway, Chicago (MDW) Southwest Airlines WN 3186 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2025-08-05 through 2025-10-01
Mon,Thu,Fri 05:00 Portland (PDX) 10:55 Midway, Chicago (MDW) Southwest Airlines WN 3617 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-10-02 through 2025-10-31
Tue,Wed,Sat 06:00 Portland (PDX) 11:55 Midway, Chicago (MDW) Southwest Airlines WN 3617 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-10-04 through 2025-11-01
Mon,Thu,Fri 08:15 Portland (PDX) 14:10 Midway, Chicago (MDW) Southwest Airlines WN 3780 Non-stop Boeing 737-700 (73W) 3:55 Effective 2025-08-07 through 2025-09-29
Sun 06:10 Portland (PDX) 12:05 Midway, Chicago (MDW) Southwest Airlines WN 3946 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-10-05 through 2025-10-26
Sat 07:45 Portland (PDX) 13:40 Midway, Chicago (MDW) Southwest Airlines WN 4013 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-11-22 through 2025-11-29
Sat 07:45 Portland (PDX) 13:40 Midway, Chicago (MDW) Southwest Airlines WN 4013 Non-stop Boeing 737-800 (73H) 3:55 Effective 2025-12-20 through 2026-01-03
Mon-Wed 05:00 Portland (PDX) 10:55 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 05:00 Portland (PDX) 10:55 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-19 through 2026-01-04
Sun 06:00 Portland (PDX) 11:55 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-11-30
Tue,Wed 06:15 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-04 through 2025-11-12
Mon-Thu 06:15 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-17 through 2025-11-20
Mon-Fri 06:15 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-02 through 2025-12-11
Mon-Wed 06:15 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-15 through 2025-12-17
Wed,Thu 06:15 Portland (PDX) 12:10 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-24 through 2026-01-01
Mon,Thu,Fri,Sun 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-02 through 2025-11-16
Mon,Fri,Sun 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-11-21 through 2025-11-28
Fri,Sun 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2025-12-07 through 2025-12-14
Thu 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2025-12-18
Mon 06:30 Portland (PDX) 12:25 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2026-01-05
Sat 10:20 Portland (PDX) 16:15 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-11-08 through 2025-11-15
Sat 10:20 Portland (PDX) 16:15 Midway, Chicago (MDW) Southwest Airlines WN 4016 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2025-12-06 through 2025-12-13
Fri 07:20 Portland (PDX) 13:15 Midway, Chicago (MDW) Southwest Airlines WN 4169 Non-stop Boeing 737-700 (73W) 3:55 Operates only on 2025-07-04

1 2

A domestic route departing from the Portland airport (PDX) and arriving at Midway, Chicago airport (MDW).
The flight distance is 1745 miles, or 2809 km.
The timezone of the departure airport is UTC-8 , and the timezone of the arrival airport is UTC-6 . 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 3:50 and 4:00.

Return (MDW-PDX) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN298

13:25

Portland (PDX)

19:20

Midway, Chicago (MDW)

Effective 2025-10-07 through 2025-10-29

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN407

05:30

Portland (PDX)

11:30

Midway, Chicago (MDW)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN407

06:00

Portland (PDX)

12:00

Midway, Chicago (MDW)

Valid until 2025-05-18

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN407

06:00

Portland (PDX)

12:00

Midway, Chicago (MDW)

Operates only on 2025-06-01

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN407

06:15

Portland (PDX)

12:15

Midway, Chicago (MDW)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN407

06:45

Portland (PDX)

12:45

Midway, Chicago (MDW)

Valid until 2025-05-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN914

10:50

Portland (PDX)

16:40

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 3:50, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN1098

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN1603

14:35

Portland (PDX)

20:25

Midway, Chicago (MDW)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:50, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2149

10:35

Portland (PDX)

16:35

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2149

13:35

Portland (PDX)

19:35

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2248

13:20

Portland (PDX)

19:15

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2248

13:50

Portland (PDX)

19:45

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2248

13:50

Portland (PDX)

19:45

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2321

06:05

Portland (PDX)

12:00

Midway, Chicago (MDW)

Effective 2025-06-08 through 2025-08-03

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2668

09:20

Portland (PDX)

15:15

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2678

06:00

Portland (PDX)

12:00

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2678

06:00

Portland (PDX)

12:00

Midway, Chicago (MDW)

Effective 2025-08-09 through 2025-09-27

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2678

06:05

Portland (PDX)

12:05

Midway, Chicago (MDW)

Effective 2025-08-10 through 2025-08-24

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2678

06:05

Portland (PDX)

12:05

Midway, Chicago (MDW)

Effective 2025-09-07 through 2025-09-28

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2678

06:10

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN2678

06:55

Portland (PDX)

12:55

Midway, Chicago (MDW)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2735

05:50

Portland (PDX)

11:45

Midway, Chicago (MDW)

Effective 2025-06-05 through 2025-07-03

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2735

05:50

Portland (PDX)

11:45

Midway, Chicago (MDW)

Effective 2025-07-07 through 2025-08-04

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2735

06:20

Portland (PDX)

12:15

Midway, Chicago (MDW)

Effective 2025-06-07 through 2025-08-02

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN2735

08:55

Portland (PDX)

14:50

Midway, Chicago (MDW)

Effective 2025-06-10 through 2025-07-30

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2927

12:30

Portland (PDX)

18:25

Midway, Chicago (MDW)

Operates only on 2025-05-25

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3186

13:30

Portland (PDX)

19:30

Midway, Chicago (MDW)

Effective 2025-08-05 through 2025-10-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN3617

05:00

Portland (PDX)

10:55

Midway, Chicago (MDW)

Effective 2025-10-02 through 2025-10-31

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN3617

06:00

Portland (PDX)

11:55

Midway, Chicago (MDW)

Effective 2025-10-04 through 2025-11-01

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN3780

08:15

Portland (PDX)

14:10

Midway, Chicago (MDW)

Effective 2025-08-07 through 2025-09-29

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3946

06:10

Portland (PDX)

12:05

Midway, Chicago (MDW)

Effective 2025-10-05 through 2025-10-26

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4013

07:45

Portland (PDX)

13:40

Midway, Chicago (MDW)

Effective 2025-11-22 through 2025-11-29

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4013

07:45

Portland (PDX)

13:40

Midway, Chicago (MDW)

Effective 2025-12-20 through 2026-01-03

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-800 (73H)

Southwest Airlines WN4016

05:00

Portland (PDX)

10:55

Midway, Chicago (MDW)

Effective 2025-11-25 through 2025-12-01

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

05:00

Portland (PDX)

10:55

Midway, Chicago (MDW)

Effective 2025-12-19 through 2026-01-04

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:00

Portland (PDX)

11:55

Midway, Chicago (MDW)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:15

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-11-04 through 2025-11-12

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:15

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-11-17 through 2025-11-20

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:15

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-12-02 through 2025-12-11

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:15

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-12-15 through 2025-12-17

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:15

Portland (PDX)

12:10

Midway, Chicago (MDW)

Effective 2025-12-24 through 2026-01-01

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Effective 2025-11-02 through 2025-11-16

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Effective 2025-11-21 through 2025-11-28

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Effective 2025-12-07 through 2025-12-14

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

06:30

Portland (PDX)

12:25

Midway, Chicago (MDW)

Operates only on 2026-01-05

Mon

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Southwest Airlines WN4016

10:20

Portland (PDX)

16:15

Midway, Chicago (MDW)

Effective 2025-11-08 through 2025-11-15

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN4016

10:20

Portland (PDX)

16:15

Midway, Chicago (MDW)

Effective 2025-12-06 through 2025-12-13

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN4169

07:20

Portland (PDX)

13:15

Midway, Chicago (MDW)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 3:55, non-stop
Boeing 737-700 (73W)

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A domestic route departing from the Portland airport (PDX) and arriving at Midway, Chicago airport (MDW).
The flight distance is 1745 miles, or 2809 km.
The timezone of the departure airport is UTC-8 , and the timezone of the arrival airport is UTC-6 . 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 3:50 and 4:00.

Return (MDW-PDX) flights

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