Chicago (MDW) to Portland (PDX) flights
Southwest Airlines flies nonstop from Chicago Midway International Airport to Portland International Airport, with about 19 flights a week in July 2026. The 1,751-mile flight takes about 4h 19m gate to gate.
- Distance
- 1,751 mi · 2,818 km
- Flight time
- 4h 19m
- Airlines
- 1
- Seats filled
- 85%
Airlines flying MDW to PDX
| Airline | Flights a week | Aircraft | Passengers (12 months) | Flight time |
|---|---|---|---|---|
| Southwest Airlines | 19 | Boeing 737 MAX 8, Boeing 737-800, Boeing 737-700 / MAX 7 | 97,500 | 4h 19m |
Airlines are the operating carrier: regional airlines such as SkyWest or Horizon often fly under a larger airline's brand.
MDW to PDX flight schedule
4 flight numbers flew this route in August 2026, 2 of them almost daily. The first usually leaves at 10:40am and the last at 9:20pm. 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 806Southwest Airlines | 10:40am | 12:50pm | 20 | 45% |
| WN 4246Southwest Airlines | 6:30pm | 8:45pm | 28 | 43% |
| WN 4840Southwest Airlines | 8:50pm | 11:05pm | 16 | 13% |
| WN 265Southwest Airlines | 9:20pm | 11:30pm | 4 | n/a |
Is MDW to PDX on time?
From September 2025 to August 2026, 59% of 674 flights arrived within 15 minutes of schedule and 1% were cancelled. Flights leaving around 3pm were the most punctual (84%), those around 4pm the least (35%). Most delay time was caused by late-arriving aircraft (45%).
| Airline | Flights | On time | Average delay | Cancelled |
|---|---|---|---|---|
| Southwest Airlines | 674 | 59% | 23 min | 1% |
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 | 34 | 68% | |
| 8am to 9am | 38 | 81% | |
| 10am to 11am | 170 | 69% | |
| 2pm to 3pm | 22 | 81% | |
| 3pm to 4pm | 43 | 84% | |
| 4pm to 5pm | 51 | 35% | |
| 5pm to 6pm | 16 | 44% | |
| 6pm to 7pm | 29 | 45% | |
| 8pm to 9pm | 89 | 52% | |
| 9pm to 10pm | 123 | 47% | |
| 10pm to 11pm | 24 | 50% |
Flights by month
| Month | Flights | Flights, relative | Passengers |
|---|---|---|---|
| August 2025 | 84 | 12,593 | |
| September 2025 | 81 | 11,533 | |
| October 2025 | 54 | 7,799 | |
| November 2025 | 29 | 3,824 | |
| December 2025 | 31 | 4,527 | |
| January 2026 | 31 | 3,633 | |
| February 2026 | 28 | 3,627 | |
| March 2026 | 56 | 7,937 | |
| April 2026 | 59 | 7,760 | |
| May 2026 | 61 | 8,885 | |
| June 2026 | 79 | 12,180 | |
| July 2026 | 83 | 13,202 |
Related
Source: US Department of Transportation, T-100 Segment data, August 2025 to July 2026.