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

Select flight date:
FLIGHT SCHEDULE
Direct Flights:
Sun 05:10 Portland (PDX) 11:05 Chicago Midway (MDW)
Southwest Airlines WN 130 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-06-07 through 2026-08-02
Mon,Thu,Fri 05:20 Portland (PDX) 11:15 Chicago Midway (MDW)
Southwest Airlines WN 280 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-03-05 through 2026-04-06
Sat 05:20 Portland (PDX) 11:15 Chicago Midway (MDW)
Southwest Airlines WN 280 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-07 through 2026-04-04
Tue,Wed 05:25 Portland (PDX) 11:20 Chicago Midway (MDW)
Southwest Airlines WN 280 Non-stop Boeing 737-700 (Scimitar Winglets) 3:55 Effective 2026-03-10 through 2026-04-01
Sun 06:15 Portland (PDX) 12:10 Chicago Midway (MDW)
Southwest Airlines WN 280 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-03-08 through 2026-04-05
Mon,Thu,Fri 11:20 Portland (PDX) 17:20 Chicago Midway (MDW)
Southwest Airlines WN 323 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-08-06 through 2026-09-28
Mon,Thu,Fri 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 930 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-12 through 2026-02-16
Thu,Fri,Sun 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 930 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-20 through 2026-03-01
Sat 07:15 Portland (PDX) 13:15 Chicago Midway (MDW)
Southwest Airlines WN 930 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-02-14 through 2026-02-28
Mon,Thu,Fri 06:05 Portland (PDX) 11:55 Chicago Midway (MDW)
Southwest Airlines WN 1148 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-06-04 through 2026-08-03
Mon,Thu,Fri 05:10 Portland (PDX) 11:05 Chicago Midway (MDW)
Southwest Airlines WN 1162 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-09 through 2026-06-01
Sun 05:20 Portland (PDX) 11:15 Chicago Midway (MDW)
Southwest Airlines WN 1162 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-04-12 through 2026-05-17
Sun 05:20 Portland (PDX) 11:15 Chicago Midway (MDW)
Southwest Airlines WN 1162 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2026-05-31
Tue,Wed 05:40 Portland (PDX) 11:35 Chicago Midway (MDW)
Southwest Airlines WN 1162 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-07 through 2026-06-03
Sat 08:00 Portland (PDX) 13:55 Chicago Midway (MDW)
Southwest Airlines WN 1162 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-11 through 2026-05-30
Sat 06:00 Portland (PDX) 11:55 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-01-10 through 2026-02-07
Mon-Fri 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-06 through 2026-01-14
Tue-Fri,Sun 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-18 through 2026-01-23
Mon-Fri 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-26 through 2026-02-04
Tue,Wed,Sun 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-08 through 2026-02-11
Tue,Wed 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-18 through 2026-03-04
Thu,Fri,Sun 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-11 through 2026-01-16
Mon,Sun 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-01-19 through 2026-01-25
Thu,Fri,Sun 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-01 through 2026-02-06
Mon,Sun 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-09 through 2026-02-15
Mon,Tue,Thu 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Effective 2026-02-17 through 2026-02-23
Mon 06:45 Portland (PDX) 12:40 Chicago Midway (MDW)
Southwest Airlines WN 2884 Non-stop Boeing 737-800 (73H) 3:55 Operates only on 2026-03-02
Mon,Thu,Fri 06:10 Portland (PDX) 12:05 Chicago Midway (MDW)
Southwest Airlines WN 3130 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-08-06 through 2026-09-28
Tue,Wed 10:55 Portland (PDX) 16:55 Chicago Midway (MDW)
Southwest Airlines WN 3130 Non-stop Boeing 737 MAX 8 (7M8) 4:00 Effective 2026-08-04 through 2026-09-30
Sun 10:55 Portland (PDX) 16:55 Chicago Midway (MDW)
Southwest Airlines WN 3130 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-08-09 through 2026-09-27
Daily 23:30 Portland (PDX) 05:25 Chicago Midway (MDW)
Southwest Airlines WN 3131 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-08-04 through 2026-09-30
The flight arrives 1 day after departure.
Tue,Wed 11:15 Portland (PDX) 17:10 Chicago Midway (MDW)
Southwest Airlines WN 3202 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-06-09 through 2026-07-29
Mon,Thu,Fri 11:50 Portland (PDX) 17:45 Chicago Midway (MDW)
Southwest Airlines WN 3202 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-06-04 through 2026-08-03
Daily 23:30 Portland (PDX) 05:20 Chicago Midway (MDW)
Southwest Airlines WN 3203 Non-stop Boeing 737 MAX 8 (7M8) 3:50 Effective 2026-06-04 through 2026-08-03
The flight arrives 1 day after departure.
Sat 06:05 Portland (PDX) 11:55 Chicago Midway (MDW)
Southwest Airlines WN 3325 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-06-06 through 2026-08-01
Tue,Wed 06:00 Portland (PDX) 11:50 Chicago Midway (MDW)
Southwest Airlines WN 3669 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-06-09 through 2026-07-29
Daily 23:55 Portland (PDX) 05:50 Chicago Midway (MDW)
Southwest Airlines WN 3708 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Effective 2026-04-07 through 2026-06-03
The flight arrives 1 day after departure.
Sat 07:45 Portland (PDX) 13:40 Chicago Midway (MDW)
Southwest Airlines WN 4013 Non-stop Boeing 737-800 (73H) 3:55 Valid until 2026-01-03
Mon,Tue,Fri,Sun 05:00 Portland (PDX) 10:55 Chicago Midway (MDW)
Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2026-01-04
Wed,Thu 06:15 Portland (PDX) 12:10 Chicago Midway (MDW)
Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Valid until 2026-01-01
Mon 06:30 Portland (PDX) 12:25 Chicago Midway (MDW)
Southwest Airlines WN 4016 Non-stop Boeing 737 MAX 8 (7M8) 3:55 Operates only on 2026-01-05
Sat 23:50 Portland (PDX) 06:40 Chicago Midway (MDW)
Southwest Airlines WN 4089 Non-stop Boeing 737-800 (73H) 3:50 Operates only on 2026-03-07
The flight arrives 1 day after departure.
Thu,Fri 23:55 Portland (PDX) 05:45 Chicago Midway (MDW)
Southwest Airlines WN 4161 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-03-05 through 2026-03-06
The flight arrives 1 day after departure.
Daily 23:55 Portland (PDX) 05:45 Chicago Midway (MDW)
Southwest Airlines WN 4161 Non-stop Boeing 737-800 (73H) 3:50 Effective 2026-03-08 through 2026-04-06
The flight arrives 1 day after departure.
Sat 07:35 Portland (PDX) 13:35 Chicago Midway (MDW)
Southwest Airlines WN 4867 Non-stop Boeing 737-800 (73H) 4:00 Effective 2026-08-08 through 2026-09-26


All airlines flying from Portland (PDX) to Chicago Midway (MDW).
Select flight date:
FLIGHT SCHEDULE
Direct Flights:

Effective 2026-06-07 through 2026-08-02
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-05 through 2026-04-06
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-03-07 through 2026-04-04
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-10 through 2026-04-01
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-700 (Scimitar Winglets)

Direct Flights:

Effective 2026-03-08 through 2026-04-05
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-12 through 2026-02-16
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-20 through 2026-03-01
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-14 through 2026-02-28
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-09 through 2026-06-01
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-12 through 2026-05-17
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-05-31
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-04-11 through 2026-05-30
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-10 through 2026-02-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-01-06 through 2026-01-14
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-01-18 through 2026-01-23
Mon
-
Tue
Wed
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-01-26 through 2026-02-04
Mon
Tue
Wed
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-08 through 2026-02-11
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-18 through 2026-03-04
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-01-11 through 2026-01-16
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-01-19 through 2026-01-25
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-01 through 2026-02-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-09 through 2026-02-15
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-02-17 through 2026-02-23
Mon
Tue
Wed
-
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Operates only on 2026-03-02
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-06 through 2026-09-28
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 4:00, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-08-09 through 2026-09-27
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
Duration: 4:00, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-08-04 through 2026-09-30
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Effective 2026-06-04 through 2026-08-03
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Duration: 3:50, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-06-06 through 2026-08-01
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-06-09 through 2026-07-29
Mon
-
Tue
Wed
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:50, non-stop
Boeing 737-800 (73H)

Direct Flights:

Effective 2026-04-07 through 2026-06-03
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)
The flight arrives 1 day after departure.

Direct Flights:

Valid until 2026-01-03
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:55, non-stop
Boeing 737-800 (73H)

Direct Flights:

Valid until 2026-01-04
Mon
Tue
Wed
-
Thu
-
Fri
Sat
-
Sun
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Valid until 2026-01-01
Mon
-
Tue
-
Wed
Thu
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-01-05
Mon
Tue
-
Wed
-
Thu
-
Fri
-
Sat
-
Sun
-
Duration: 3:55, non-stop
Boeing 737 MAX 8 (7M8)

Direct Flights:

Operates only on 2026-03-07
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 3:50, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-03-05 through 2026-03-06
Mon
-
Tue
-
Wed
-
Thu
Fri
Sat
-
Sun
-
Duration: 3:50, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-03-08 through 2026-04-06
Mon
Tue
Wed
Thu
Fri
Sat
Sun
Duration: 3:50, non-stop
Boeing 737-800 (73H)
The flight arrives 1 day after departure.

Direct Flights:

Effective 2026-08-08 through 2026-09-26
Mon
-
Tue
-
Wed
-
Thu
-
Fri
-
Sat
Sun
-
Duration: 4:00, non-stop
Boeing 737-800 (73H)
  • A domestic route departing from the Portland airport (PDX) and arriving at Chicago Midway 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.