A sample of one-way prices for one traveler from Roame’s fare cache. Points, fees, and seats describe the same observation. Availability can change; confirm with the loyalty program before transferring points.
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Did you mean Flights from Portland to Chicago?
Chicago
United StatesMDW
Chicago Midway International Airport
Portland
United StatesPWM
Portland International Jetport Airport
Chicago Midway International Airport (MDW) serves Chicago; Portland International Jetport Airport (PWM) serves Portland.
The airports are 893 miles apart by great-circle distance.
Roame's current schedule feed shows nonstop service from MDW to PWM.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Published schedule dates span Oct 3, 2026 – May 30, 2027.
These are marketing airlines, including codeshare sellers. This list does not identify the operating airline for each flight; check the flight details before booking.
Chicago Midway International Airport (MDW) is the origin airport and Portland International Jetport Airport (PWM) is the destination airport.
MDW and PWM are approximately 893 miles apart by great-circle distance.
Yes. Roame's current schedule feed shows nonstop service from MDW to PWM.
Marketing airlines listed in the current schedule, including codeshare sellers, are Southwest Airlines (WN). This list does not identify the operating airline for each flight; check the flight details before booking.
Aircraft listed in the current schedule include Boeing 737-800 Winglets (73H), Boeing 737 MAX 8 (7M8) and 7S7.