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$203+ 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — PWM
May 20 — May 271
Tue 5/20
Tue 5/27
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 May 15, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$315
(Sun Country Air)

One-way from

$203
(Booking.com)

Popular in

September

Cheapest in

April

Average price

$873
Provider with most accurate pricing for Oakland-Portland flight deals.
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Provider most trusted by Cheapflights users for Oakland-Portland flights.
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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. 3% potential increase in price ($22 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($34 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 15, 2025.

This Southwest deal was found by Cheapflights users on 5/13. 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 9/55:15 amOAK - PWM
1 stop8h 50mSouthwest
Tue 9/91:50 pmPWM - OAK
2 stops10h 50mSouthwest
Deal found 5/13$350
This Mytrip deal was found by Cheapflights users on 5/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/255:30 amOAK - PWM
2 stops27h 09mMultiple Airlines
Sat 6/2812:58 pmPWM - OAK
1 stop30h 47mMultiple Airlines
Deal found 5/15$381
This Trip.com deal was found by Cheapflights users on 5/15. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:15 pmOAK - PWM
1 stop14h 20mSun Country Air
Sun 7/2012:46 pmPWM - OAK
1 stop31h 05mSun Country Air
Deal found 5/15$438
This Delta deal was found by Cheapflights users on 5/15. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/245:55 amOAK - PWM
2 stops13h 03mDelta
Tue 9/3012:30 pmPWM - OAK
2 stops14h 23mDelta
Deal found 5/15$1,052

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 May 15, 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

Fri 9/5

5:15 am-5:05 pm

1 stop8h 50m

Portland

Tue 9/9

1:50 pm-9:40 pm

2 stops10h 50m

$350

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 6/25

5:30 am-11:39 am

2 stops27h 09m

Portland

Sat 6/28

12:58 pm-4:45 pm

1 stop30h 47m

$381

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 7/17

6:15 pm-11:35 am

1 stop14h 20m

Portland

Sun 7/20

12:46 pm-4:51 pm

1 stop31h 05m

$438

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Wed 9/24

5:55 am-9:58 pm

2 stops13h 03m

Portland

Tue 9/30

12:30 pm-11:53 pm

2 stops14h 23m

$1,052

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 7/17

6:15 pm-11:35 am

1 stop14h 20m

$203

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Sun 6/8

5:50 am-7:15 pm

2 stops10h 25m

$265

OaklandPortland

OAK - PWM

OAKPWM

Oakland

Thu 7/17

6:00 am-11:35 am

2 stops26h 35m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/15

Compare providers for flights from Oakland to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Oakland to Portland in May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Oakland, California-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Oakland, California-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Oakland, California-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Oakland, California-Portland, Maine flights, Cheapflights users trust Expedia the most. Expedia has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Oakland, California-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 May 15, 2025.
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Southwest
8.0
Very good
4,291 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.
Sun Country Air
6.9
Okay
346 reviews
Southwest
8.0
Very good
4,291 reviews

Entertainment

7.6

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Merlyn,Feb 2025

LAX - SMF

New Terminal is neat, lost of stores and places to catch a bite.

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 are the cheapest airlines flying from Oakland, California to Portland, Maine round-trip?

    Cheapflights users have booked flights from Oakland, California to Portland, Maine round-trip from $315. Other airlines that can offer you cheap pricing are Southwest, from $350, and Delta, from $471. These flights start at 53% lower than the current average price 3 months from now.

  • 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 Oakland?

Book flights to Oakland if you plan to visit one of these locations
North Conway
Bath
Brunswick
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 May 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$389Average$678FlexibilityNo cancel feeOn-time63%

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