Portland to Chicago flights
Direct and connecting flights from Portland International Jetport Airport (PWM) to Chicago Midway International Airport (MDW) — airlines, aircraft types, and the safety record for this route.
Route FAQ
How long does the flight from Portland to Chicago take?
Flight time from Portland (PWM) to Chicago (MDW) depends on routing, aircraft type, and whether the flight is direct or connecting. A direct flight typically reflects great-circle distance plus winds, while one-stop options can add several hours depending on the layover airport. The typical block time and frequency we have observed for this route are shown above.
Which airlines fly from Portland to Chicago?
Airline availability for PWM to MDW changes by season and sometimes week to week as carriers adjust capacity. The airlines and aircraft types observed operating this route, both direct and connecting, are listed below based on real flight-tracking data.
Are there direct flights from Portland to Chicago?
Direct (nonstop) availability on PWM to MDW varies by date, day of week, and season. Busy city pairs usually have multiple daily nonstops, while thinner routes may only have direct service a few days per week or only during peak seasons.
No fatal or serious occurrence involving any operator on this pair in the last 90 days.
- Southwest Airlines40
| Carrier | Sightings / 90d | Safety events |
|---|---|---|
| Southwest Airlines | 3 sightings | No recorded events |
Planning PWM → MDW
PWM to MDW is a short-haul route of 1,437 km (893 mi). See the return MDW → PWM route.
Alternative airports near Portland: Brunswick (NHZ) — 40 km, Lewiston (LEW) — 45 km, Fryeburg (FRY) — 64 km.
Alternative airports near Chicago: Chicago (CGX) — 14 km, Chicago (ORD) — 25 km, Gary (GYY) — 34 km.