Chicago (MDW) to Portland (PWM) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to Portland International Jetport, with about 7 flights a week in July 2026. The 895-mile flight takes about 2h 8m gate to gate.
- Distance
- 895 mi · 1,440 km
- Flight time
- 2h 8m
- Airlines
- 1
- Seats filled
- 86%
Airlines flying MDW to PWM
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 7 | Boeing 737-800, Boeing 737-700 / MAX 7, Boeing 737 MAX 8 | 21,303 | 2h 8m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MDW to PWM flight schedule
2 flight numbers flew this route in August 2026. The first usually leaves at 6:10pm and the last at 6:50pm. Times are local and can change; check with the airline before you book.
| Flight | Departs | Arrives | Days flown in August 2026 | On time (12 months) |
|---|---|---|---|---|
| WN 431Southwest Airlines | 6:10pm | 9:30pm | 16 | 60% |
| WN 300Southwest Airlines | 6:50pm | 10:05pm | 12 | 75% |
Is MDW to PWM on time?
From September 2025 to August 2026, 73% of 151 flights arrived within 15 minutes of schedule and 0.7% were cancelled. Flights leaving around 10am were the most punctual (100%), those around 6pm the least (57%). Most delay time was caused by late-arriving aircraft (50%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 151 | 73% | 19 min | 0.7% |
Airlines as sold: flights operated by regional partners count under the airline on the ticket. Average delay is across all completed flights, early arrivals counted as zero.
On-time arrivals by departure time
| Scheduled departure | Flights | On time, relative | On time |
|---|---|---|---|
| 10am to 11am | 13 | 100% | |
| 11am to 12pm | 15 | 87% | |
| 1pm to 2pm | 33 | 88% | |
| 6pm to 7pm | 67 | 57% | |
| 7pm to 8pm | 13 | 69% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 31 | 4,413 | |
| September 2025 | 30 | 4,109 | |
| October 2025 | 30 | 3,804 | |
| November 2025 | 1 | 42 | |
| June 2026 | 27 | 4,077 | |
| July 2026 | 32 | 4,858 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.