Book low fares from Chicago (Midway) to Portland, OR, with Southwest Airlines®. It’s easy to find the Chicago Midway International Airport to Portland International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.
Explore your options and book your Chicago (Midway) to Portland, OR, flight with Southwest today!
Best Airline in the U.S. and North America & Best Economy and Low Cost Airline in North America.
Chicago (Midway), IL to Portland, OR
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 26 travel days available.
Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our Coronavirus Travel Information page for information about potential restrictions on air travel.
Average flight time: 4 hours 27 minutes
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Portland International Airport (PDX)
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Other popular flights from Chicago
View our interactive map†Based on DOT published scheduled average flights Monday-Friday between 10/30/2020 and 12/31/2020, as of 11/2/2020.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
At Southwest, we know it takes more than great deals on Portland, OR, airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Portland, OR, the best it can be. Find out more about the Southwest® Experience before you book your Chicago Midway International Airport to Portland International Airport flight.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. And when you search for your next flight to Portland, OR, you know you won’t be surprised at checkout. Low fares, no hidden fees. That’s our Transfarency® promise. And, as always, bags fly free. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Looking for tours, activities, and more hidden gems to add to your Portland, OR, adventure? Explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How long is the flight from Chicago (Midway) to Portland, OR?
The average flight time from Chicago (Midway) to Portland, OR, is 4 hours 27 minutes.
How many Southwest flights from Chicago (Midway) to Portland, OR, occur daily?
There are 10 flights daily from Chicago (Midway) to Portland, OR, on Southwest Airlines.
Does Southwest fly nonstop from Chicago (Midway) to Portland, OR?
Southwest flies nonstop from Chicago (Midway) to Portland, OR, once daily.
What day is it cheapest to fly from Chicago (Midway) to Portland, OR?
To find the cheapest day and time to fly Chicago (Midway) to Portland, OR, with Southwest, check out our Low Fare Calendar.
Can I rent a car at Portland International Airport?
You can rent a car at Portland International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Chicago (Midway) to Portland, OR?
Yes! Flights from Chicago (Midway) to Portland, OR—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Chicago (Midway) to Portland, OR?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Chicago (Midway) to Portland, OR, with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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