Chicago (MDW) to Portland (PWM) flights
One airline flies nonstop from Chicago (MDW) to Portland (PWM): 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 MDW to PWM
- Southwest AirlinesNot in an allianceWho books it
MDW to PWM 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)Southwest Airlines, then Breeze Airways
- Via Columbus (CMH)Southwest Airlines, then Breeze Airways
- Via New York (LGA)Southwest Airlines, then American Airlines and Delta Air Lines
- Via Philadelphia (PHL)Southwest Airlines, then American Airlines
- Via Cincinnati (CVG)Southwest Airlines, then Breeze Airways
- Via Baltimore (BWI)Southwest Airlines the whole way
- Via Washington (DCA)Southwest Airlines, then American Airlines
- Via Norfolk (ORF)Southwest Airlines, then Breeze Airways
- Via Raleigh/Durham (RDU)Southwest Airlines, then Breeze Airways
- Via Charlotte (CLT)Southwest Airlines, then American 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)Southwest Airlines, then Breeze Airways
MDW to PWM: common questions
Which airlines fly nonstop from MDW to PWM?
Southwest Airlines flies nonstop from Chicago (MDW) to Portland (PWM).
How far is Chicago from Portland by plane?
Chicago (MDW) and Portland (PWM) 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 MDW to PWM 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 PWM with taxes and fees.
Where can I connect between Chicago and Portland?
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.