| 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 |