Portland (PWM) to Chicago (MDW) flights
One airline flies nonstop from Portland (PWM) to Chicago (MDW): Southwest Airlines. The two airports are 892 miles (1,436 km) apart. There are also 15 ways to fly it with one stop, through Detroit, Pittsburgh and Columbus and more.
Airlines flying nonstop from PWM to MDW
- Southwest AirlinesNot in an allianceWho books it
PWM to MDW with one stop
15 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Pittsburgh (PIT)Breeze Airways, then Southwest Airlines
- Via Columbus (CMH)Breeze Airways, then Southwest Airlines
- Via New York (LGA)American Airlines and Delta Air Lines, then Southwest Airlines
- Via Philadelphia (PHL)American Airlines, then Southwest Airlines
- Via Cincinnati (CVG)Breeze Airways, then Southwest Airlines
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Washington (DCA)American Airlines, then Southwest Airlines
- Via Norfolk (ORF)Breeze Airways, then Southwest Airlines
- Via Raleigh/Durham (RDU)Breeze Airways, then Southwest Airlines
- Via Charlotte (CLT)American Airlines, then Southwest Airlines
- Via Nashville (BNA)Southwest Airlines the whole way
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Atlanta (ATL)Delta Air Lines the whole way
- Via Charleston (CHS)Breeze Airways, then Southwest Airlines
PWM to MDW: common questions
Which airlines fly nonstop from PWM to MDW?
Southwest Airlines flies nonstop from Portland (PWM) to Chicago (MDW).
How far is Portland from Chicago by plane?
Portland (PWM) and Chicago (MDW) are 892 miles (1,436 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PWM to MDW cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for PWM to MDW with taxes and fees.
Where can I connect between Portland and Chicago?
The most direct connections are through Detroit (DTW), Pittsburgh (PIT), Columbus (CMH), New York (LGA) and Philadelphia (PHL). On 5 of them the same airline flies both flights, for example Delta Air Lines through Detroit.
More routes
Routes are scheduled nonstop flights. The route data is refreshed monthly; this list was last checked November 11, 2026. Seasonal routes and new launches can be missing or end early, so confirm with the airline before you book. Distances are great-circle, the shortest path between the two airports.