Great-circle route MDW ↔ PDX. Faint dots are other airports, for geographic context. Download this map — free to reuse with a link back to this page.
Frequencies below are per direction, from our most recent schedule sample.
| Direction | Frequency | Days | Airlines |
|---|---|---|---|
| MDW → PDX Chicago to Portland |
19/wk | Daily | Southwest Airlines |
| PDX → MDW Portland to Chicago |
— | — | Southwest Airlines |
Where a direction shows “—” we track it as an operating nonstop but hold no schedule sample for it — we would rather show nothing than guess.
In 2025, airlines reported 169,056 passengers on 1,193 flights between MDW and PDX — about 463 a day — filling 87% of the 195,143 seats flown. Southwest Airlines Co. carried the most passengers (100%).
Source: US DOT T-100 segment reports — actual airline-reported traffic, scheduled service only, both directions combined. Cargo and charter flights excluded.
Southwest Airlines is the only airline flying the MDW–PDX nonstop.
Recent scheduled departures on this route have used the Boeing 737.
Aircraft assignments change by season and by time of day.
On a long east–west route like this one the two directions do not take the same time. Aircraft flying eastbound ride the mid-latitude jet stream and typically arrive earlier than the westbound leg, which flies into it. The difference is commonly 30 to 90 minutes on transatlantic and transpacific flights, and it varies by season. The estimate above does not model wind — treat it as a midpoint and check the airline's own timetable for the block time on your date.
The distance between Chicago Midway International Airport and Portland International Airport is 1,747 miles, or 2,812 kilometres.
| Great-circle distance | 1,747 mi |
| Kilometres | 2,812 km |
| Nautical miles | 1,518 nmi |
Measured airport to airport. The actual track is longer — aircraft follow airways, avoid restricted airspace and route around weather.
Yes. Southwest Airlines flies the route nonstop, with about 19 departures a week across both directions. The route is in our live nonstop dataset, last seeded 2026-07-07.
About 3h 58m in the air. That is a great-circle estimate from the 1,747-mile distance, not a scheduled block time — an airline's published time will differ by roughly 15 to 45 minutes depending on routing, winds and taxi.
Southwest Airlines.
In 2025, airlines reported 169,056 passengers on 1,193 scheduled flights between MDW and PDX — about 463 a day — filling 87% of the seats flown. Source: US DOT T-100 segment reports, both directions combined.
Recent scheduled departures have used the Boeing 737. Assignments change by season and by time of day.
