$76 Cheap Flights from Chicago (MDW) to Portland (PWM)

View $76 flight on Sat, Nov 1, 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 $76 for one-way flights and $161 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Sat, Nov 1 - Tue, Nov 4
MDW
Chicago
PWM
Portland
$161 Roundtrip, found 2 days ago
$161
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sat, Nov 1 from Chicago to Portland, returning Tue, Nov 4, priced at $161 found 2 days ago
Southwest Airlines
Mon, Oct 27 - Fri, Oct 31
MDW
Chicago
PWM
Portland
$166 Roundtrip, found 2 hours ago
$166
Roundtrip
found 2 hours ago
Select Southwest Airlines flight, departing Mon, Oct 27 from Chicago to Portland, returning Fri, Oct 31, priced at $166 found 2 hours ago
Southwest Airlines
Thu, Oct 23 - Tue, Oct 28
MDW
Chicago
PWM
Portland
$169 Roundtrip, found 10 hours ago
$169
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Chicago to Portland, returning Tue, Oct 28, priced at $169 found 10 hours ago
Southwest Airlines
Tue, Sep 23 - Tue, Sep 30
MDW
Chicago
PWM
Portland
$171 Roundtrip, found 12 hours ago
$171
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Tue, Sep 30, priced at $171 found 12 hours ago
Southwest Airlines
Tue, Sep 23 - Tue, Sep 30
MDW
Chicago
PWM
Portland
$176 Roundtrip, found 12 hours ago
$176
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Tue, Sep 23 from Chicago to Portland, returning Tue, Sep 30, priced at $176 found 12 hours ago
Southwest Airlines
Mon, Nov 3 - Tue, Nov 4
MDW
Chicago
PWM
Portland
$179 Roundtrip, just found
$179
Roundtrip
just found
Select Southwest Airlines flight, departing Mon, Nov 3 from Chicago to Portland, returning Tue, Nov 4, priced at $179 just found
Southwest Airlines
Wed, Sep 3 - Wed, Sep 10
MDW
Chicago
PWM
Portland
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Wed, Sep 3 from Chicago to Portland, returning Wed, Sep 10, priced at $179 found 1 day ago
Southwest Airlines
Thu, Oct 23 - Tue, Oct 28
MDW
Chicago
PWM
Portland
$184 Roundtrip, found 10 hours ago
$184
Roundtrip
found 10 hours ago
Select Southwest Airlines flight, departing Thu, Oct 23 from Chicago to Portland, returning Tue, Oct 28, priced at $184 found 10 hours ago
Delta
Mon, Oct 27 - Fri, Oct 31
MDW
Chicago
PWM
Portland
$191 Roundtrip, found 2 hours ago
$191
Roundtrip
found 2 hours ago
Select Delta flight, departing Mon, Oct 27 from Chicago to Portland, returning Fri, Oct 31, priced at $191 found 2 hours ago
Frontier Airlines
Fri, Aug 22 - Sat, Aug 30
MDW
Chicago
PWM
Portland
$238 Roundtrip, found 1 day ago
$238
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Fri, Aug 22 from Chicago to Portland, returning Sat, Aug 30, priced at $238 found 1 day ago

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

August is typically the cheapest month to fly

From $189 - $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 $275
PWM
Portland Intl. Jetport
CheapestClosest
Average driving time to city center8 min
Flights from $275
Flights from Chicago (MDW) to Portland (PWM)
Origin airport
Midway Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$161
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 November. 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 $76 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?
Snag a cheap one-way flight from $76 or cheap return flight from $161 from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
November is the cheapest month to fly from MDW to PWM. Traveling outside of peak seasons is often the key to scoring lower fares.
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 Midway Intl. Airport (MDW) to Portland Intl. Jetport Airport (PWM)?
Expedia's filter tool lets you easily compare airlines, flight times and baggage options all in one place. Choose your preferences, then sort by "Price (lowest to highest)" to find the carrier with the cheapest MDW to PWM flight.
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.