Portland (PDX) to Chicago (MDW) flights
One airline flies nonstop from Portland (PDX) to Chicago (MDW): Southwest Airlines. The two airports are 1,747 miles (2,811 km) apart. There are also 37 ways to fly it with one stop, through Bozeman, Minneapolis and Spokane and more.
Airlines flying nonstop from PDX to MDW
- Southwest AirlinesNot in an allianceWho books it
PDX to MDW with one stop
37 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Bozeman (BZN)Alaska Airlines, then Southwest Airlines
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Spokane (GEG)Alaska Airlines, then Southwest Airlines
- Via Boise (BOI)Alaska Airlines, then Southwest Airlines
- Via Seattle (SEA)Alaska Airlines and Delta Air Lines, then Southwest Airlines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Denver (DEN)Southwest Airlines the whole way
+1 - Via Salt Lake City (SLC)Alaska Airlines and Delta Air Lines, then Southwest Airlines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Reno (RNO)Alaska Airlines, then Southwest Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Albuquerque (ABQ)Alaska Airlines, then Southwest Airlines
- Via Sacramento (SMF)Southwest Airlines the whole way
- Via Las Vegas (LAS)Southwest Airlines the whole way
- Via Columbus (CMH)American Airlines, then Southwest Airlines
PDX to MDW: common questions
Which airlines fly nonstop from PDX to MDW?
Southwest Airlines flies nonstop from Portland (PDX) to Chicago (MDW).
How far is Portland from Chicago by plane?
Portland (PDX) and Chicago (MDW) are 1,747 miles (2,811 km) apart along the great circle, the shortest path a flight can take. Connections add distance on top.
How many miles does PDX 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 PDX to MDW with taxes and fees.
Where can I connect between Portland and Chicago?
The most direct connections are through Bozeman (BZN), Minneapolis (MSP), Spokane (GEG), Boise (BOI) and Seattle (SEA). On 15 of them the same airline flies both flights, for example Delta Air Lines through Minneapolis.
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.