$136 Cheap Flights from Oakland (OAK) to Portland (PWM)

View $136 flight on Tue, Jul 29, 2025Opens in a new window

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Find available prices by choosing your travel dates.

Cheap Flights from Oakland to Portland (OAK-PWM)

Prices were available within the past 7 days and start at $136 for one-way flights and $274 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Southwest Airlines
Tue, Jul 29 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$274 Roundtrip, found 6 days ago
$274
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jul 29 from Oakland to Portland, returning Thu, Aug 7, priced at $274 found 6 days ago
Southwest Airlines
Thu, Jul 31 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$287 Roundtrip, found 6 days ago
$287
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Oakland to Portland, returning Thu, Aug 7, priced at $287 found 6 days ago
Delta
Mon, Oct 27 - Sat, Nov 8
OAK
Oakland
PWM
Portland
$307 Roundtrip, found 4 days ago
$307
Roundtrip
found 4 days ago
Select Delta flight, departing Mon, Oct 27 from Oakland to Portland, returning Sat, Nov 8, priced at $307 found 4 days ago
Southwest Airlines
Tue, Jul 29 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$314 Roundtrip, found 6 days ago
$314
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jul 29 from Oakland to Portland, returning Thu, Aug 7, priced at $314 found 6 days ago
Southwest Airlines
Mon, Aug 4 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$324 Roundtrip, found 1 day ago
$324
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Mon, Aug 4 from Oakland to Portland, returning Thu, Aug 7, priced at $324 found 1 day ago
Southwest Airlines
Tue, Sep 2 - Mon, Oct 6
OAK
Oakland
PWM
Portland
$326 Roundtrip, found 3 days ago
$326
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Oakland to Portland, returning Mon, Oct 6, priced at $326 found 3 days ago
Southwest Airlines
Thu, Jul 31 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$327 Roundtrip, found 6 days ago
$327
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Jul 31 from Oakland to Portland, returning Thu, Aug 7, priced at $327 found 6 days ago
Southwest Airlines
Tue, Jul 29 - Thu, Aug 7
OAK
Oakland
PWM
Portland
$329 Roundtrip, found 6 days ago
$329
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Tue, Jul 29 from Oakland to Portland, returning Thu, Aug 7, priced at $329 found 6 days ago
Southwest Airlines
Tue, Sep 2 - Mon, Oct 6
OAK
Oakland
PWM
Portland
$332 Roundtrip, found 3 days ago
$332
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Sep 2 from Oakland to Portland, returning Mon, Oct 6, priced at $332 found 3 days ago
Sun Country Airlines
Sun, Jul 6 - Mon, Jul 21
OAK
Oakland
PWM
Portland
$467 Roundtrip, found 2 days ago
$467
Roundtrip
found 2 days ago
Select Sun Country Airlines flight, departing Sun, Jul 6 from Oakland to Portland, returning Mon, Jul 21, priced at $467 found 2 days ago
Flights from Oakland (OAK) to Portland (PWM)
Origin airport
Oakland Intl.
Destination airport
Portland Intl. Jetport
Airlines serving
Delta, Southwest Airlines
Roundtrip price
$274
Distance
2705 mi

Oakland to Portland Flights

The cheapest times to fly from Oakland 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 Oakland to Portland are during the month of July. You can find some of the cheapest flights from Oakland to Portland with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Oakland to Portland

Sunday is one of the best days to book for cheap flights from Oakland 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 Oakland 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 Oakland to Portland in 2025. You can also book with separate airlines for your outbound and return journeys, from $136 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 Oakland 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 Oakland 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 Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM) cost?
Discover the latest flight deals from OAK to PWM by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from OAK to PWM?
The cheapest flights from OAK 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.
What is the cheapest airline that flies from OAK to PWM?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from OAK to PWM. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM)?
Nonstop flights from Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your dates and select either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from OAK to PWM?
Friday is generally the busiest day for flights, while Tuesday tends to be the quietest.* Keep in mind that flight schedules can change based on a number of factors, including the time of year and airline.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM)?
Choose a flight from Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM) that leaves before 3 PM to reduce the risk of cancellations and delays. Departures later than this have a 22% higher chance of being canceled, on average.**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 Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM) last-minute?
Booking your plane ticket from OAK to PWM right before your getaway is usually more expensive. However, if you’re flexible with your travel dates and times, you could land a cheap last-minute fare.
Is it cheaper to book an OAK to PWM flight and hotel package?
Securing an OAK to PWM flight and hotel package is typically cheaper than booking separately. With Expedia, you can enjoy the convenience of organizing your trip in one place. Choose from our wide range of hotels and then add car rentals, flights and activities 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 Oakland Intl. Airport (OAK) to Portland Intl. Jetport Airport (PWM)?
If you booked your OAK to PWM flight in the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal for more details.

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*Available to One Key members.