Did you mean Flights from Chicago to Portland?
Portland
United StatesPWM
Portland International Jetport Airport
Chicago
United StatesMDW
Chicago Midway International Airport
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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Portland International Jetport Airport (PWM) serves Portland; Chicago Midway International Airport (MDW) serves Chicago.
The airports are 893 miles apart by great-circle distance.
Roame's current schedule feed shows nonstop service from PWM to MDW.
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 1, 2026 – Mar 31, 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.
Portland International Jetport Airport (PWM) is the origin airport and Chicago Midway International Airport (MDW) is the destination airport.
PWM and MDW are approximately 893 miles apart by great-circle distance.
Yes. Roame's current schedule feed shows nonstop service from PWM to MDW.
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), 7S7 and JET.