All airlines flying from Chicago Midway (MDW) to Portland (PDX).
| FLIGHT SCHEDULE |
|---|
| Direct Flights: |
| Sun
10:25
Chicago Midway (MDW)
12:40
Portland (PDX) Southwest Airlines WN 4246 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-09 through 2026-09-27 |
| Mon,Thu,Fri
18:25
Chicago Midway (MDW)
20:40
Portland (PDX) Southwest Airlines WN 4246 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-06 through 2026-09-28 |
| Sat
22:30
Chicago Midway (MDW)
00:55
Portland (PDX) Southwest Airlines WN 4497 Non-stop Boeing 737 MAX 8 (7M8) 4:25 Operates only on 2026-03-07 The flight arrives 1 day after departure. |
| Mon,Thu,Fri
16:40
Chicago Midway (MDW)
19:00
Portland (PDX) Southwest Airlines WN 4765 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-04 through 2026-08-03 |
| Tue,Wed
17:30
Chicago Midway (MDW)
19:50
Portland (PDX) Southwest Airlines WN 4765 Non-stop Boeing 737 MAX 8 (7M8) 4:20 Effective 2026-06-09 through 2026-07-29 |
| Sat
18:00
Chicago Midway (MDW)
20:15
Portland (PDX) Southwest Airlines WN 4840 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-08 through 2026-09-26 |
| Mon,Thu,Fri
20:50
Chicago Midway (MDW)
23:05
Portland (PDX) Southwest Airlines WN 4840 Non-stop Boeing 737 MAX 8 (7M8) 4:15 Effective 2026-08-06 through 2026-09-28 |
| Non-Direct Flights: |
| Tue,Wed
15:40
Chicago Midway (MDW)
20:45
Portland (PDX) Southwest Airlines WN 826 1-stop Boeing 737-700 (Scimitar Winglets) 7:05 Effective 2026-04-07 through 2026-06-03 |
| Mon,Thu,Fri
05:00
Chicago Midway (MDW)
09:55
Portland (PDX) Southwest Airlines WN 1377 1-stop Boeing 737 MAX 8 (7M8) 6:55 Effective 2026-06-04 through 2026-08-03 |
| Mon,Thu,Fri
10:10
Chicago Midway (MDW)
16:40
Portland (PDX) Southwest Airlines WN 2433 2-stop Boeing 737-700 (Scimitar Winglets) 8:30 Effective 2026-06-04 through 2026-08-03 |
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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.
