Portland (PWM) to Chicago (MDW) flights
Southwest Airlines flies nonstop from Portland International Jetport to Chicago Midway International Airport, with about 7 flights a week in July 2026. The 895-mile flight takes about 2h 26m gate to gate.
- Distance
- 895 mi · 1,440 km
- Flight time
- 2h 26m
- Airlines
- 1
- Seats filled
- 91%
Airlines flying PWM to MDW
| 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 | 22,429 | 2h 26m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
PWM to MDW flight schedule
2 flight numbers flew this route in August 2026, 1 of them almost daily. The first usually leaves at 7:40am and the last at 3:40pm. 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 3338Southwest Airlines | 7:40am | 9:10am | 24 | 96% |
| WN 2751Southwest Airlines | 3:40pm | 5:15pm | 4 | n/a |
Is PWM to MDW on time?
From September 2025 to August 2026, 88% of 151 flights arrived within 15 minutes of schedule and 0% were cancelled. Flights leaving around 10am were the most punctual (96%), those around 3pm the least (46%). Most delay time was caused by late-arriving aircraft (44%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 151 | 88% | 10 min | 0% |
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 |
|---|---|---|---|
| 7am to 8am | 71 | 90% | |
| 10am to 11am | 24 | 96% | |
| 2pm to 3pm | 13 | 92% | |
| 3pm to 4pm | 13 | 46% | |
| 4pm to 5pm | 17 | 88% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 30 | 4,694 | |
| September 2025 | 30 | 4,647 | |
| October 2025 | 31 | 4,032 | |
| November 2025 | 1 | 99 | |
| June 2026 | 27 | 4,028 | |
| July 2026 | 31 | 4,929 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.