$90 Cheap Flights from Chicago (MDW) to Portland (PWM)

View $90 flight on Sun, Aug 31, 2025Opens in a new window

Popular airlines from Chicago Midway Airport (MDW) to Portland Intl. Jetport Airport (PWM)

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Cheap Flights from Chicago to Portland (MDW-PWM)

Prices were available within the past 7 days and start at $90 for one-way flights and $241 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Sep 6 - Sat, Sep 20
MDW
Chicago
PWM
Portland
$241 Roundtrip, found 16 hours ago
$241
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to Portland, returning Sat, Sep 20, priced at $241 found 16 hours ago
Southwest Airlines
Sat, Sep 6 - Sat, Sep 20
MDW
Chicago
PWM
Portland
$246 Roundtrip, found 16 hours ago
$246
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to Portland, returning Sat, Sep 20, priced at $246 found 16 hours ago
Delta
Sat, Jul 5 - Fri, Jul 11
MDW
Chicago
PWM
Portland
$248 Roundtrip, just found
$248
Roundtrip
just found
Select Delta flight, departing Sat, Jul 5 from Chicago to Portland, returning Fri, Jul 11, priced at $248 just found
Delta
Tue, Aug 5 - Wed, Aug 13
MDW
Chicago
PWM
Portland
$251 Roundtrip, just found
$251
Roundtrip
just found
Select Delta flight, departing Tue, Aug 5 from Chicago to Portland, returning Wed, Aug 13, priced at $251 just found
Delta
Wed, Aug 6 - Wed, Aug 13
MDW
Chicago
PWM
Portland
$252 Roundtrip, found 1 hour ago
$252
Roundtrip
found 1 hour ago
Select Delta flight, departing Wed, Aug 6 from Chicago to Portland, returning Wed, Aug 13, priced at $252 found 1 hour ago
Southwest Airlines
Wed, Aug 20 - Thu, Aug 21
MDW
Chicago
PWM
Portland
$255 Roundtrip, found 1 day ago
$255
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Aug 20 from Chicago to Portland, returning Thu, Aug 21, priced at $255 found 1 day ago
Delta
Sat, Aug 16 - Thu, Aug 21
MDW
Chicago
PWM
Portland
$257 Roundtrip, found 1 hour ago
$257
Roundtrip
found 1 hour ago
Select Delta flight, departing Sat, Aug 16 from Chicago to Portland, returning Thu, Aug 21, priced at $257 found 1 hour ago
Delta
Sat, Jul 5 - Fri, Jul 11
MDW
Chicago
PWM
Portland
$258 Roundtrip, just found
$258
Roundtrip
just found
Select Delta flight, departing Sat, Jul 5 from Chicago to Portland, returning Fri, Jul 11, priced at $258 just found
Southwest Airlines
Sun, Jul 6 - Fri, Jul 11
MDW
Chicago
PWM
Portland
$259 Roundtrip, just found
$259
Roundtrip
just found
Select Southwest Airlines flight, departing Sun, Jul 6 from Chicago to Portland, returning Fri, Jul 11, priced at $259 just found
Southwest Airlines
Sat, Sep 6 - Sat, Sep 20
MDW
Chicago
PWM
Portland
$260 Roundtrip, found 3 days ago
$260
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to Portland, returning Sat, Sep 20, priced at $260 found 3 days ago

Find the cheapest month to fly from Chicago (MDW) to Portland (PWM)

August is typically the cheapest month to fly

From $177 - $623 per traveler.

Graph displaying average flight prices per month

Alternative airports near Portland

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to Portland Intl. Jetport PWM. Cheapest and Closest option available. Average driving time to city center is 8 minutes. Flights from $728
PWM
Portland Intl. Jetport
CheapestClosest
Average driving time to city center8 min
Flights from $728
Flights from Chicago (MDW) to Portland (PWM)
Origin airport
Midway Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
Delta, Frontier Airlines, Southwest Airlines
Roundtrip price
$241
Distance
892 mi
Average flight time
2 hours 15 mins

Chicago to Portland Flights

The cheapest times to fly from Chicago to Portland

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Portland are during the month of September. You can find some of the cheapest flights from Chicago to Portland with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Chicago to Portland

Sunday is one of the best days to book for cheap flights from Chicago to Portland: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Chicago to Portland

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $90 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Portland flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Portland airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Frequently asked questions

How much does a flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) cost?
You can land affordable return tickets from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) starting at $231. Book a seat and get ready to go. This information is based on the cheapest price found on Expedia for this return journey departing within the next three months. This airfare is for a Southwest Airlines and American Airlines flight leaving MDW on June 30 2025 and touching down at PWM. The price was last updated on June 19 2025 and has not changed since.
What is the cheapest month to fly from MDW to PWM?
The cheapest flights from MDW to PWM are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
Which airlines fly direct from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
You can't catch a direct flight to Portland Intl. Jetport Airport (PWM) from Chicago, IL (MDW-Midway Intl.). However, you can easily travel to Portland without any layovers by departing from O'Hare Intl. Airport (ORD).
What is the cheapest airline that flies from MDW to PWM?
At the moment, the cheapest carrier offering one-way flights from MDW to PWM is Southwest Airlines. You can take off on this route from $130. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on August 12 2025. Prices were last updated on June 19 2025 and have not changed since.
How many flights per day from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
There aren't any daily nonstop flights departing from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM). But you can choose flights with layovers. Filter your search on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from MDW to PWM?
Typically you'll find the greatest selection of flight options on a Friday. Tuesdays are often the quietest.* But this can vary based on the time of year, carrier and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What airline has the least delays from MDW to PWM?
Consider traveling with Southwest Airlines if you'd like to go straight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) without any holdups. This carrier has the best track record for punctuality, with an on-time performance of 87%. Want to be updated if anything changes? You can keep an eye on your flight status using the Expedia App.
What is the best time to fly from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
Book a flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) that takes off before 3 PM to reduce the likelihood of delays. Departures after this hour are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) last-minute?
Waiting until just before your departure to book your flight from MDW to PWM generally means paying more. While you might find some last-minute discounts, there's no guarantee. Be flexible with your itinerary to boost your chances of scoring a bargain.
Is it cheaper to book a MDW to PWM flight and hotel package?
Opting for a MDW to PWM flight and hotel package tends to be cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip all in one place. Pick from our extensive range of accommodations and then add activities, car rentals and flights to your booking. Bundle it all together, and you could save hundreds of dollars.
Can I cancel or change the date of my flight from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
Generally, it's possible to cancel or reschedule your MDW to PWM flight. However, if it's been more than 24 hours since booking, additional fees may apply. Check your airline's policies in your itinerary to see what changes are allowed and if any costs are involved. You'll also find more details on our Customer Service portal.

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*Available to One Key members.