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$194+ Cheap flights from Oakland, CA to Portland, ME (OAK - PWM)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
Aug 22 — Aug 291
Fri 8/22
Fri 8/29
1 adult, Economy
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Cheap flight deals from Oakland to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Oakland (OAK) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 17, 2025.

Round-trip from

$423
(Southwest)

One-way from

$194
(Southwest)

Popular in

March

Cheapest in

January

Average price

$431
From Oakland to Portland
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One-way flight from Oakland to Portland
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Highest demand for flights based on searches. 22% potential increase in price ($139 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Oakland to Portland

Cheapest flights from Oakland to Portland
Explore the most affordable flight options available from Oakland to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 17, 2025.

This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/207:30 amOAK - PWM
2 stops11h 30mSouthwest
Tue 9/305:50 amPWM - OAK
2 stops12h 05mSouthwest
Deal found 8/17$423
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amOAK - PWM
2 stops12h 00mSouthwest
Tue 12/212:45 pmPWM - OAK
2 stops11h 25mSouthwest
Deal found 8/14$453
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:10 pmOAK - PWM
2 stops11h 40mSouthwest
Mon 9/158:25 amPWM - OAK
2 stops13h 05mSouthwest
Deal found 8/15$583
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/165:05 pmOAK - PWM
2 stops13h 35mSouthwest
Sat 8/235:45 amPWM - OAK
2 stops12h 25mSouthwest
Deal found 8/15$659
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:10 pmOAK - PWM
2 stops12h 05mSouthwest
Sun 9/215:35 amPWM - OAK
2 stops12h 00mSouthwest
Deal found 8/16$697
This Southwest deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/117:10 pmOAK - PWM
2 stops11h 40mSouthwest
Sun 9/145:35 amPWM - OAK
2 stops12h 00mSouthwest
Deal found 8/15$744
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/307:00 amOAK - PWM
2 stops12h 00mSouthwest
Mon 9/15:50 amPWM - OAK
2 stops15h 40mSouthwest
Deal found 8/16$745

Cheapflights Fare Finder

 
Customize your flight search to find flights from Oakland to Portland that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2025.
Use the filters below to find and compare flights from Oakland to Portland that are best for you.

Fly from

Oakland

Fly to

Portland

Route

Depart

Return

Price

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 9/20

7:30 am-10:00 pm

2 stops11h 30m

Portland

Tue 9/30

5:50 am-2:55 pm

2 stops12h 05m

$423

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 8/30

7:00 am-10:00 pm

2 stops12h 00m

Portland

Tue 12/2

12:45 pm-9:10 pm

2 stops11h 25m

$453

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 9/11

7:10 pm-9:50 am

2 stops11h 40m

Portland

Mon 9/15

8:25 am-6:30 pm

2 stops13h 05m

$583

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 9/19

7:10 pm-10:15 am

2 stops12h 05m

Portland

Sun 9/21

5:35 am-2:35 pm

2 stops12h 00m

$697

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 9/11

7:10 pm-9:50 am

2 stops11h 40m

Portland

Sun 9/14

5:35 am-2:35 pm

2 stops12h 00m

$744

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sat 8/30

7:00 am-10:00 pm

2 stops12h 00m

Portland

Mon 9/1

5:50 am-6:30 pm

2 stops15h 40m

$745

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 8/29

7:10 pm-10:15 am

2 stops12h 05m

Portland

Mon 9/1

5:50 am-6:30 pm

2 stops15h 40m

$880

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Fri 9/5

5:15 am-5:05 pm

1 stop8h 50m

$194

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sun 8/31

8:15 am-9:15 pm

1 stop10h 00m

$199

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sun 8/31

6:00 am-11:40 am

3 stops26h 40m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/16

Showing 1-10 of 15 results
1
2

Best time to book a flight from Oakland to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Oakland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Oakland to Portland

What is the cheapest month to book a flight from Oakland, California to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $296). Flying from Oakland, California to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Portland. Reviews last updated August 17, 2025.
Read reviews from past customers who have flown Southwest from Oakland to Portland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Overall

8.0

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Oakland to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What is the cheapest airline to fly from Oakland, California to Portland, Maine round-trip?

    Cheapflights users have booked flights from Oakland, California to Portland, Maine round-trip from $389.

  • Can I find deals for flights from Oakland to Portland that include hotel bookings?

    Yes. In addition to deals on Oakland to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Oakland to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Oakland to Portland.

  • Can I find deals for business class flights from Oakland to Portland?

    Yes. Cheapflights offers flight deals from Oakland to Portland by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Oakland, California to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Oakland, California to Portland, Maine (average of $296). Flying from Oakland, California to Portland, Maine in July is currently the most expensive (average of $394). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top airline flying from Oakland to Portland

Discover the top airline that operate flights from Oakland to Portland. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$389Average$678FlexibilityNo cancel feeOn-time63%

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