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

View $100 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 $100 for one-way flights and $141 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Oct 28 - Wed, Oct 29
MDW
Chicago
PWM
Portland
$141 Roundtrip, found 3 days ago
$141
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Portland, returning Wed, Oct 29, priced at $141 found 3 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $142 found 4 days ago
Southwest Airlines
Tue, Oct 28 - Wed, Oct 29
MDW
Chicago
PWM
Portland
$143 Roundtrip, found 3 days ago
$143
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Portland, returning Wed, Oct 29, priced at $143 found 3 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$144 Roundtrip, found 4 days ago
$144
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $144 found 4 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$147 Roundtrip, found 4 days ago
$147
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $147 found 4 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$152 Roundtrip, found 4 days ago
$152
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $152 found 4 days ago
Southwest Airlines
Tue, Oct 28 - Wed, Oct 29
MDW
Chicago
PWM
Portland
$153 Roundtrip, found 3 days ago
$153
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Oct 28 from Chicago to Portland, returning Wed, Oct 29, priced at $153 found 3 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $154 found 4 days ago
Southwest Airlines
Wed, Oct 29 - Sat, Nov 1
MDW
Chicago
PWM
Portland
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Wed, Oct 29 from Chicago to Portland, returning Sat, Nov 1, priced at $157 found 4 days ago
Delta
Tue, Oct 28 - Wed, Oct 29
MDW
Chicago
PWM
Portland
$174 Roundtrip, found 3 days ago
$174
Roundtrip
found 3 days ago
Select Delta flight, departing Tue, Oct 28 from Chicago to Portland, returning Wed, Oct 29, priced at $174 found 3 days ago

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

January is typically the cheapest month to fly

From $194 - $523 per traveler.

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 $100 or cheap return flight from $141 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)?
October 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.

Travel information

Travel information

Origin airport
Midway Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$140
Distance
892 mi
Average flight time
2 hours 15 mins

Book with confidence

Book with confidence

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 October. 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.

 

Chicago to Portland Flights

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*Available to One Key members.