$100 Cheap Flights from Chicago (MDW) to Portland (PWM)

View $100 flight on Fri, Oct 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 $100 for one-way flights and $214 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Sep 23 - Sat, Sep 27
MDW
Chicago
PWM
Portland
$214 Roundtrip, found 5 days ago
$214
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Sat, Sep 27, priced at $214 found 5 days ago
Southwest Airlines
Sat, Sep 6 - Wed, Sep 10
MDW
Chicago
PWM
Portland
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Sep 6 from Chicago to Portland, returning Wed, Sep 10, priced at $217 found 1 day ago
Southwest Airlines
Sun, Aug 31 - Wed, Sep 3
MDW
Chicago
PWM
Portland
$218 Roundtrip, found 3 hours ago
$218
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sun, Aug 31 from Chicago to Portland, returning Wed, Sep 3, priced at $218 found 3 hours ago
Southwest Airlines
Sun, Aug 31 - Wed, Sep 3
MDW
Chicago
PWM
Portland
$223 Roundtrip, found 3 hours ago
$223
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Sun, Aug 31 from Chicago to Portland, returning Wed, Sep 3, priced at $223 found 3 hours ago
Southwest Airlines
Wed, Sep 3 - Tue, Sep 16
MDW
Chicago
PWM
Portland
$227 Roundtrip, found 17 hours ago
$227
Roundtrip
found 17 hours ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Chicago to Portland, returning Tue, Sep 16, priced at $227 found 17 hours ago
Delta
Sat, Aug 23 - Sat, Aug 30
MDW
Chicago
PWM
Portland
$228 Roundtrip, found 3 hours ago
$228
Roundtrip
found 3 hours ago
Select Delta flight, departing Sat, Aug 23 from Chicago to Portland, returning Sat, Aug 30, priced at $228 found 3 hours ago
Southwest Airlines
Tue, Sep 2 - Wed, Sep 3
MDW
Chicago
PWM
Portland
$232 Roundtrip, found 23 hours ago
$232
Roundtrip
found 23 hours ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Chicago to Portland, returning Wed, Sep 3, priced at $232 found 23 hours ago
Southwest Airlines
Tue, Aug 26 - Sat, Aug 30
MDW
Chicago
PWM
Portland
$233 Roundtrip, found 6 hours ago
$233
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Tue, Aug 26 from Chicago to Portland, returning Sat, Aug 30, priced at $233 found 6 hours ago
Southwest Airlines
Sat, Aug 23 - Tue, Aug 26
MDW
Chicago
PWM
Portland
$237 Roundtrip, just found
$237
Roundtrip
just found
Select Southwest Airlines flight, departing Sat, Aug 23 from Chicago to Portland, returning Tue, Aug 26, priced at $237 just found
Frontier Airlines
Fri, Aug 22 - Sat, Aug 30
MDW
Chicago
PWM
Portland
$238 Roundtrip, found 3 hours ago
$238
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Fri, Aug 22 from Chicago to Portland, returning Sat, Aug 30, priced at $238 found 3 hours ago

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

August is typically the cheapest month to fly

From $178 - $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 $273
PWM
Portland Intl. Jetport
CheapestClosest
Average driving time to city center8 min
Flights from $273
Flights from Chicago (MDW) to Portland (PWM)
Origin airport
Midway Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$214
Distance
892 mi
Average flight time
3 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 $100 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 $201. 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 United flight leaving MDW on August 18 2025 and touching down at PWM. The price was last updated on July 23 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 $116. This fare is based on the lowest price found on Expedia departing within the next three months. The flight takes off from MDW on September 7 2025. Prices were last updated on July 23 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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Chicago nearby Airports

Chicago

O'Hare Intl. to Portland
$182.39
*Available to One Key members.