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

FLIGHT SCHEDULE
Direct Flights:
Tue,Wed 08:30 Midway, Chicago (MDW) 10:50 Portland (PDX) Southwest Airlines WN 339 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-08-05 through 2025-10-01
Mon,Thu,Fri 07:50 Midway, Chicago (MDW) 10:00 Portland (PDX) Southwest Airlines WN 383 Non-stop Boeing 737-700 (73W) 4:10 Effective 2025-08-07 through 2025-09-29
Sat 14:15 Midway, Chicago (MDW) 16:45 Portland (PDX) Southwest Airlines WN 519 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2025-11-22 through 2025-11-29
Sat 14:15 Midway, Chicago (MDW) 16:45 Portland (PDX) Southwest Airlines WN 519 Non-stop Boeing 737-700 (Scimitar Winglets) 4:30 Effective 2025-12-20 through 2026-01-03
Thu 08:35 Midway, Chicago (MDW) 11:05 Portland (PDX) Southwest Airlines WN 572 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-11-27
Sat 08:15 Midway, Chicago (MDW) 10:30 Portland (PDX) Southwest Airlines WN 621 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-08-09 through 2025-09-27
Mon,Thu,Fri 07:50 Midway, Chicago (MDW) 10:10 Portland (PDX) Southwest Airlines WN 1155 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-10-02 through 2025-10-31
Tue,Wed 16:05 Midway, Chicago (MDW) 18:25 Portland (PDX) Southwest Airlines WN 1656 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-10 through 2025-07-30
Sat 21:10 Midway, Chicago (MDW) 23:35 Portland (PDX) Southwest Airlines WN 1656 Non-stop Boeing 737-700 (73W) 4:25 Effective 2025-06-07 through 2025-08-02
Mon,Thu,Fri 22:05 Midway, Chicago (MDW) 00:25 Portland (PDX) Southwest Airlines WN 1656 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-05 through 2025-07-03 The flight arrives 1 day after departure.
Mon,Thu,Fri 22:05 Midway, Chicago (MDW) 00:25 Portland (PDX) Southwest Airlines WN 1656 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-07-07 through 2025-08-04 The flight arrives 1 day after departure.
Sun 22:25 Midway, Chicago (MDW) 00:45 Portland (PDX) Southwest Airlines WN 1656 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-08 through 2025-08-03 The flight arrives 1 day after departure.
Tue,Wed 15:50 Midway, Chicago (MDW) 18:05 Portland (PDX) Southwest Airlines WN 1766 Non-stop Boeing 737-700 (73W) 4:15 Effective 2025-08-05 through 2025-10-01
Sun 20:20 Midway, Chicago (MDW) 22:35 Portland (PDX) Southwest Airlines WN 1766 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Operates only on 2025-08-31
Mon,Thu,Fri 20:50 Midway, Chicago (MDW) 23:05 Portland (PDX) Southwest Airlines WN 1766 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-08-07 through 2025-09-29
Sun 22:25 Midway, Chicago (MDW) 00:40 Portland (PDX) Southwest Airlines WN 1766 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-08-10 through 2025-08-24 The flight arrives 1 day after departure.
Sun 22:25 Midway, Chicago (MDW) 00:40 Portland (PDX) Southwest Airlines WN 1766 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-09-07 through 2025-09-28 The flight arrives 1 day after departure.
Sat 09:40 Midway, Chicago (MDW) 12:15 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-11-08 through 2025-11-15
Sat 09:40 Midway, Chicago (MDW) 12:15 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:35 Effective 2025-12-06 through 2025-12-13
Tue,Wed 16:50 Midway, Chicago (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-04 through 2025-11-12
Mon-Thu 16:50 Midway, Chicago (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-17 through 2025-11-20
Mon-Fri 16:50 Midway, Chicago (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-12-02 through 2025-12-11
Mon-Wed 16:50 Midway, Chicago (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-12-15 through 2025-12-17
Wed,Thu 16:50 Midway, Chicago (MDW) 19:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-12-24 through 2026-01-01
Mon-Wed 19:30 Midway, Chicago (MDW) 22:00 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-25 through 2025-12-01
Mon,Tue,Fri,Sun 19:30 Midway, Chicago (MDW) 22:00 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-12-19 through 2026-01-04
Sun 21:40 Midway, Chicago (MDW) 00:10 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-11-30 The flight arrives 1 day after departure.
Mon,Thu,Fri,Sun 21:50 Midway, Chicago (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-02 through 2025-11-16 The flight arrives 1 day after departure.
Mon,Fri,Sun 21:50 Midway, Chicago (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-11-21 through 2025-11-28 The flight arrives 1 day after departure.
Fri,Sun 21:50 Midway, Chicago (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Effective 2025-12-07 through 2025-12-14 The flight arrives 1 day after departure.
Thu 21:50 Midway, Chicago (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2025-12-18 The flight arrives 1 day after departure.
Mon 21:50 Midway, Chicago (MDW) 00:20 Portland (PDX) Southwest Airlines WN 2039 Non-stop Boeing 737 MAX 8 (7M8) 4:30 Operates only on 2026-01-05 The flight arrives 1 day after departure.
Sat 07:45 Midway, Chicago (MDW) 10:05 Portland (PDX) Southwest Airlines WN 2121 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-07 through 2025-08-02
Tue,Wed 07:50 Midway, Chicago (MDW) 10:10 Portland (PDX) Southwest Airlines WN 2121 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-10 through 2025-07-30
Sun 08:15 Midway, Chicago (MDW) 10:35 Portland (PDX) Southwest Airlines WN 2121 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2025-06-08 through 2025-08-03
Sat 14:10 Midway, Chicago (MDW) 16:25 Portland (PDX) Southwest Airlines WN 2308 Non-stop Boeing 737-700 (73W) 4:15 Effective 2025-08-09 through 2025-09-27
Mon,Thu-Sat 16:15 Midway, Chicago (MDW) 18:35 Portland (PDX) Southwest Airlines WN 2765 Non-stop Boeing 737-700 (73W) 4:20 Valid until 2025-06-02
Tue,Wed 16:30 Midway, Chicago (MDW) 18:50 Portland (PDX) Southwest Airlines WN 2765 Non-stop Boeing 737-700 (73W) 4:20 Valid until 2025-06-04
Fri 14:05 Midway, Chicago (MDW) 16:25 Portland (PDX) Southwest Airlines WN 3199 Non-stop Boeing 737-700 (73W) 4:20 Operates only on 2025-07-04
Sun 18:30 Midway, Chicago (MDW) 20:55 Portland (PDX) Southwest Airlines WN 3337 Non-stop Boeing 737-700 (Scimitar Winglets) 4:25 Effective 2025-10-05 through 2025-10-26
Mon,Thu,Fri 15:55 Midway, Chicago (MDW) 18:15 Portland (PDX) Southwest Airlines WN 3698 Non-stop Boeing 737-700 (73W) 4:20 Effective 2025-06-05 through 2025-07-03
Mon,Thu,Fri 15:55 Midway, Chicago (MDW) 18:15 Portland (PDX) Southwest Airlines WN 3698 Non-stop Boeing 737-700 (73W) 4:20 Effective 2025-07-07 through 2025-08-04
Sat 16:00 Midway, Chicago (MDW) 18:20 Portland (PDX) Southwest Airlines WN 3698 Non-stop Boeing 737-700 (73W) 4:20 Effective 2025-06-07 through 2025-08-02
Sun 08:00 Midway, Chicago (MDW) 10:15 Portland (PDX) Southwest Airlines WN 3735 Non-stop Boeing 737-700 (73W) 4:15 Effective 2025-08-10 through 2025-08-24
Sun 08:00 Midway, Chicago (MDW) 10:15 Portland (PDX) Southwest Airlines WN 3735 Non-stop Boeing 737-700 (73W) 4:15 Effective 2025-09-07 through 2025-09-28
Sun 08:55 Midway, Chicago (MDW) 11:10 Portland (PDX) Southwest Airlines WN 3735 Non-stop Boeing 737-700 (73W) 4:15 Operates only on 2025-08-31
Mon,Thu,Fri 14:55 Midway, Chicago (MDW) 17:10 Portland (PDX) Southwest Airlines WN 3735 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-08-07 through 2025-09-29
Tue,Wed 20:30 Midway, Chicago (MDW) 22:45 Portland (PDX) Southwest Airlines WN 3735 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2025-08-05 through 2025-10-01
Sat 15:35 Midway, Chicago (MDW) 17:55 Portland (PDX) Southwest Airlines WN 3860 Non-stop Boeing 737-700 (Scimitar Winglets) 4:20 Effective 2025-10-04 through 2025-11-01
Tue,Wed 20:25 Midway, Chicago (MDW) 22:50 Portland (PDX) Southwest Airlines WN 3860 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Effective 2025-10-07 through 2025-10-29

1 2

A domestic route departing from the Midway, Chicago 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 4:35.

Return (PDX-MDW) flights

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

FLIGHT SCHEDULE

Direct Flights:

Southwest Airlines WN339

08:30

Midway, Chicago (MDW)

10:50

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN383

07:50

Midway, Chicago (MDW)

10:00

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:10, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN519

14:15

Midway, Chicago (MDW)

16:45

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN519

14:15

Midway, Chicago (MDW)

16:45

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN572

08:35

Midway, Chicago (MDW)

11:05

Portland (PDX)

Operates only on 2025-11-27

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN621

08:15

Midway, Chicago (MDW)

10:30

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN1155

07:50

Midway, Chicago (MDW)

10:10

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1656

16:05

Midway, Chicago (MDW)

18:25

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN1656

21:10

Midway, Chicago (MDW)

23:35

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:25, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1656

22:05

Midway, Chicago (MDW)

00:25(+1)

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1656

22:05

Midway, Chicago (MDW)

00:25(+1)

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1656

22:25

Midway, Chicago (MDW)

00:45(+1)

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1766

15:50

Midway, Chicago (MDW)

18:05

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN1766

20:20

Midway, Chicago (MDW)

22:35

Portland (PDX)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN1766

20:50

Midway, Chicago (MDW)

23:05

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN1766

22:25

Midway, Chicago (MDW)

00:40(+1)

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN1766

22:25

Midway, Chicago (MDW)

00:40(+1)

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

09:40

Midway, Chicago (MDW)

12:15

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2039

09:40

Midway, Chicago (MDW)

12:15

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2039

16:50

Midway, Chicago (MDW)

19:20

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2039

16:50

Midway, Chicago (MDW)

19:20

Portland (PDX)

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

Mon

Tue

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2039

16:50

Midway, Chicago (MDW)

19:20

Portland (PDX)

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

Mon

Tue

Wed

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN2039

16:50

Midway, Chicago (MDW)

19:20

Portland (PDX)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2039

16:50

Midway, Chicago (MDW)

19:20

Portland (PDX)

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

Mon
-

Tue
-

Wed

Thu

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2039

19:30

Midway, Chicago (MDW)

22:00

Portland (PDX)

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

Mon

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2039

19:30

Midway, Chicago (MDW)

22:00

Portland (PDX)

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

Mon

Tue

Wed
-

Thu
-

Fri

Sat
-

Sun

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

Southwest Airlines WN2039

21:40

Midway, Chicago (MDW)

00:10(+1)

Portland (PDX)

Operates only on 2025-11-30

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

21:50

Midway, Chicago (MDW)

00:20(+1)

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

21:50

Midway, Chicago (MDW)

00:20(+1)

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

21:50

Midway, Chicago (MDW)

00:20(+1)

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

21:50

Midway, Chicago (MDW)

00:20(+1)

Portland (PDX)

Operates only on 2025-12-18

Mon
-

Tue
-

Wed
-

Thu

Fri
-

Sat
-

Sun
-

Duration: 4:30, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2039

21:50

Midway, Chicago (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 MAX 8 (7M8)
The flight arrives 1 day after departure.

Southwest Airlines WN2121

07:45

Midway, Chicago (MDW)

10:05

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN2121

07:50

Midway, Chicago (MDW)

10:10

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN2121

08:15

Midway, Chicago (MDW)

10:35

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

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

Southwest Airlines WN2308

14:10

Midway, Chicago (MDW)

16:25

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2765

16:15

Midway, Chicago (MDW)

18:35

Portland (PDX)

Valid until 2025-06-02

Mon

Tue
-

Wed
-

Thu

Fri

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN2765

16:30

Midway, Chicago (MDW)

18:50

Portland (PDX)

Valid until 2025-06-04

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3199

14:05

Midway, Chicago (MDW)

16:25

Portland (PDX)

Operates only on 2025-07-04

Mon
-

Tue
-

Wed
-

Thu
-

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3337

18:30

Midway, Chicago (MDW)

20:55

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:25, non-stop
Boeing 737-700 (Scimitar Winglets)

Southwest Airlines WN3698

15:55

Midway, Chicago (MDW)

18:15

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3698

15:55

Midway, Chicago (MDW)

18:15

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3698

16:00

Midway, Chicago (MDW)

18:20

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

Duration: 4:20, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3735

08:00

Midway, Chicago (MDW)

10:15

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3735

08:00

Midway, Chicago (MDW)

10:15

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3735

08:55

Midway, Chicago (MDW)

11:10

Portland (PDX)

Operates only on 2025-08-31

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat
-

Sun

Duration: 4:15, non-stop
Boeing 737-700 (73W)

Southwest Airlines WN3735

14:55

Midway, Chicago (MDW)

17:10

Portland (PDX)

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

Mon

Tue
-

Wed
-

Thu

Fri

Sat
-

Sun
-

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

Southwest Airlines WN3735

20:30

Midway, Chicago (MDW)

22:45

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

Southwest Airlines WN3860

15:35

Midway, Chicago (MDW)

17:55

Portland (PDX)

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

Mon
-

Tue
-

Wed
-

Thu
-

Fri
-

Sat

Sun
-

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

Southwest Airlines WN3860

20:25

Midway, Chicago (MDW)

22:50

Portland (PDX)

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

Mon
-

Tue

Wed

Thu
-

Fri
-

Sat
-

Sun
-

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

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A domestic route departing from the Midway, Chicago 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 4:35.

Return (PDX-MDW) flights

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