Chicago (MDW) to Portland (PDX) flights
One airline flies nonstop from Chicago (MDW) to Portland (PDX): 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 MDW to PDX
- Southwest AirlinesNot in an allianceWho books it
MDW to PDX with one stop
37 connections, most direct first. 2-stop routings and flight times are in Routes with Pro.
- Via Bozeman (BZN)Southwest Airlines, then Alaska Airlines
- Via Minneapolis (MSP)Delta Air Lines the whole way
- Via Spokane (GEG)Southwest Airlines, then Alaska Airlines
- Via Boise (BOI)Southwest Airlines, then Alaska Airlines
- Via Seattle (SEA)Southwest Airlines, then Alaska Airlines and Delta Air Lines
- Via Kansas City (MCI)Southwest Airlines the whole way
- Via Denver (DEN)Southwest Airlines the whole way
+1 - Via Salt Lake City (SLC)Southwest Airlines, then Alaska Airlines and Delta Air Lines
- Via Saint Louis (STL)Southwest Airlines the whole way
- Via Reno (RNO)Southwest Airlines, then Alaska Airlines
- Via Detroit (DTW)Delta Air Lines the whole way
- Via Albuquerque (ABQ)Southwest Airlines, then Alaska Airlines
- Via Sacramento (SMF)Southwest Airlines the whole way
- Via Las Vegas (LAS)Southwest Airlines the whole way
- Via Columbus (CMH)Southwest Airlines, then American Airlines
MDW to PDX: common questions
Which airlines fly nonstop from MDW to PDX?
Southwest Airlines flies nonstop from Chicago (MDW) to Portland (PDX).
How far is Chicago from Portland by plane?
Chicago (MDW) and Portland (PDX) 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 MDW to PDX cost?
It depends on the program: each prices the route from its own chart or dynamically. The Award Flight Pricer compares 30+ programs for MDW to PDX with taxes and fees.
Where can I connect between Chicago and Portland?
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.