$209+ Cheap flights from Portland, ME to Oakland, CA (PWM - OAK)
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 10/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — OAK
May 27 — Jun 31
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Oakland with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Portland to Oakland
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Cheapest flights from Portland to OaklandExplore the most affordable flight options available from Portland to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
Explore the most affordable flight options available from Portland to Oakland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.
This Southwest deal was found by Cheapflights users on 4/24. 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 10/306:30 am
PWM
- OAK
1 stop9h 05m
Southwest
Tue 11/37:55 am
OAK
- PWM
2 stops10h 50m
Southwest
Deal found 4/24![Southwest logo]()
$398
This Southwest deal was found by Cheapflights users on 4/25. 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.
Tue 6/301:05 pm
PWM
- OAK
2 stops9h 50m
Southwest
Mon 7/67:45 pm
OAK
- PWM
2 stops11h 10m
Southwest
Deal found 4/25![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 4/25. 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.
Tue 7/143:45 pm
PWM
- OAK
2 stops10h 35m
Southwest
Mon 7/205:10 am
OAK
- PWM
1 stop14h 00m
Southwest
Deal found 4/25![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 4/25. 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.
Tue 7/143:45 pm
PWM
- OAK
2 stops10h 35m
Southwest
Sun 7/197:15 pm
OAK
- PWM
2 stops11h 30m
Southwest
Deal found 4/25![Southwest logo]()
$457
This Southwest deal was found by Cheapflights users on 4/25. 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.
Tue 6/301:05 pm
PWM
- OAK
2 stops9h 50m
Southwest
Tue 7/77:55 pm
OAK
- PWM
2 stops11h 00m
Southwest
Deal found 4/25![Southwest logo]()
$459
This Southwest deal was found by Cheapflights users on 4/25. 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.
Wed 7/151:05 pm
PWM
- OAK
2 stops9h 50m
Southwest
Mon 7/205:10 am
OAK
- PWM
2 stops15h 55m
Southwest
Deal found 4/25![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 4/22. 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 7/93:10 pm
PWM
- OAK
2 stops12h 05m
Southwest
Tue 7/219:45 am
OAK
- PWM
2 stops10h 10m
Southwest
Deal found 4/22![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 4/25. 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.
Mon 7/135:35 am
PWM
- OAK
2 stops12h 20m
Southwest
Sun 7/197:15 pm
OAK
- PWM
2 stops11h 30m
Southwest
Deal found 4/25![Southwest logo]()
$473
This Southwest deal was found by Cheapflights users on 4/23. 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 5/812:45 pm
PWM
- OAK
2 stops11h 00m
Southwest
Tue 5/129:25 am
OAK
- PWM
2 stops10h 10m
Southwest
Deal found 4/23![Southwest logo]()
$484
Best flights from Portland to OaklandDiscover carefully curated flight deals from Portland to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
Discover carefully curated flight deals from Portland to Oakland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 27, 2026.
This Southwest deal was found by Cheapflights users on 4/25. 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.
Tue 7/143:45 pm
PWM
- OAK
2 stops10h 35m
Southwest
Mon 7/205:10 am
OAK
- PWM
1 stop14h 00m
Southwest
Deal found 4/25![Southwest logo]()
$444
This Delta deal was found by Cheapflights users on 4/22. 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.
Thu 7/911:47 am
PWM
- OAK
2 stops27h 03m
Delta
Mon 7/206:00 am
OAK
- PWM
2 stops14h 14m
Delta
Deal found 4/22![Delta logo]()
$683
This Southwest deal was found by Cheapflights users on 4/25. 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.
Wed 7/151:05 pm
PWM
- OAK
2 stops9h 50m
Southwest
Mon 7/205:10 am
OAK
- PWM
1 stop14h 00m
Southwest
Deal found 4/25![Southwest logo]()
$444
This Southwest deal was found by Cheapflights users on 4/22. 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 7/93:10 pm
PWM
- OAK
2 stops12h 05m
Southwest
Tue 7/219:45 am
OAK
- PWM
2 stops10h 10m
Southwest
Deal found 4/22![Southwest logo]()
$467
This Southwest deal was found by Cheapflights users on 4/23. 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 5/812:45 pm
PWM
- OAK
2 stops11h 00m
Southwest
Tue 5/129:25 am
OAK
- PWM
2 stops10h 10m
Southwest
Deal found 4/23![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 4/26. 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.
Mon 5/112:50 pm
PWM
- OAK
2 stops12h 15m
Southwest
Fri 5/157:45 am
OAK
- PWM
2 stops12h 40m
Southwest
Deal found 4/26![Southwest logo]()
$488
This Southwest deal was found by Cheapflights users on 4/23. 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.
Wed 7/291:05 pm
PWM
- OAK
2 stops10h 00m
Southwest
Sat 8/111:55 pm
OAK
- PWM
2 stops10h 55m
Southwest
Deal found 4/23![Southwest logo]()
$555
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sun 6/76:45 am
PWM
- OAK
1 stop8h 45m
Southwest
Tue 6/95:55 am
OAK
- PWM
1 stop12h 35m
Southwest
Deal found 4/27![Southwest logo]()
$602
Last-minute flights from Portland to OaklandDiscover last-minute flight deals from Portland to Oakland. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Oakland. Data last updated April 27, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 4/23. 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 4/305:30 am
PWM
- OAK
2 stops11h 40m
Southwest
Thu 5/711:55 pm
OAK
- PWM
2 stops11h 15m
Southwest
Deal found 4/23![Southwest logo]()
$630
This Southwest deal was found by Cheapflights users on 4/23. 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 5/812:45 pm
PWM
- OAK
2 stops11h 00m
Southwest
Tue 5/129:25 am
OAK
- PWM
2 stops10h 10m
Southwest
Deal found 4/23![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 4/27. 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 5/95:40 am
PWM
- OAK
2 stops14h 15m
Southwest
Wed 5/138:55 am
OAK
- PWM
2 stops10h 40m
Southwest
Deal found 4/27![Southwest logo]()
$560
This Southwest deal was found by Cheapflights users on 4/27. 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.
Sun 5/105:30 am
PWM
- OAK
2 stops13h 25m
Southwest
Thu 5/1411:55 pm
OAK
- PWM
2 stops11h 15m
Southwest
Deal found 4/27![Southwest logo]()
$649
This Southwest deal was found by Cheapflights users on 4/26. 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.
Mon 5/112:50 pm
PWM
- OAK
2 stops12h 15m
Southwest
Fri 5/157:45 am
OAK
- PWM
2 stops12h 40m
Southwest
Deal found 4/26![Southwest logo]()
$488
One-way flights from Portland to OaklandSearch for one-way flight options from Portland to Oakland. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
Search for one-way flight options from Portland to Oakland. Find affordable one-way fares based on user searches. Data last updated April 27, 2026.
This Southwest deal was found by Cheapflights users on 4/24. 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 10/86:30 am
PWM
- OAK
1 stop9h 05m
Southwest
Deal found 4/24![Southwest logo]()
$209
This Southwest deal was found by Cheapflights users on 4/24. 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.
Mon 6/153:10 pm
PWM
- OAK
2 stops12h 05m
Southwest
Deal found 4/24![Southwest logo]()
$214
This Southwest deal was found by Cheapflights users on 4/26. 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.
Tue 6/303:45 pm
PWM
- OAK
2 stops10h 35m
Southwest
Deal found 4/26![Southwest logo]()
$230
This Southwest deal was found by Cheapflights users on 4/26. 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.
Sun 6/285:30 am
PWM
- OAK
2 stops16h 35m
Southwest
Deal found 4/26![Southwest logo]()
$265
This Delta deal was found by Cheapflights users on 4/25. 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 5/272:05 pm
PWM
- OAK
2 stops12h 52m
Delta
Deal found 4/25![Delta logo]()
$275
This Delta deal was found by Cheapflights users on 4/26. 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.
Fri 7/104:52 pm
PWM
- OAK
2 stops9h 58m
Delta
Deal found 4/26![Delta logo]()
$425
Find flight deals from Portland to Oakland
Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Oakland (OAK). 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 April 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $419 (Southwest) |
One-way from | $209 (Southwest) |
Popular in | December |
Cheapest in | September |
Average price | $443 |
Cheapflights Fare Finder
Customize your flight search to find flights from Portland to Oakland 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 April 27, 2026.
Use the filters below to find and compare flights from Portland to Oakland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandOakland
PWM - OAK
PWMOAK
Portland
Tue 7/14
3:45 pm-11:20 pm
2 stops10h 35m
Oakland
Mon 7/20
5:10 am-10:10 pm
1 stop14h 00m
$444
PortlandOakland
PWM - OAK
PWMOAK
Portland
Wed 7/15
1:05 pm-7:55 pm
2 stops9h 50m
Oakland
Mon 7/20
5:10 am-10:10 pm
1 stop14h 00m
$444
PortlandOakland
PWM - OAK
PWMOAK
Portland
Thu 7/9
3:10 pm-12:15 am
2 stops12h 05m
Oakland
Tue 7/21
9:45 am-10:55 pm
2 stops10h 10m
$467
PortlandOakland
PWM - OAK
PWMOAK
Portland
Fri 5/8
12:45 pm-8:45 pm
2 stops11h 00m
Oakland
Tue 5/12
9:25 am-10:35 pm
2 stops10h 10m
$484
PortlandOakland
PWM - OAK
PWMOAK
Portland
Mon 5/11
2:50 pm-12:05 am
2 stops12h 15m
Oakland
Fri 5/15
7:45 am-11:25 pm
2 stops12h 40m
$488
Quickest round-trip
PortlandOakland
PWM - OAK
PWMOAK
Portland
Wed 7/29
1:05 pm-8:05 pm
2 stops10h 00m
Oakland
Sat 8/1
11:55 pm-1:50 pm
2 stops10h 55m
$555
PortlandOakland
PWM - OAK
PWMOAK
Portland
Sun 6/7
6:45 am-12:30 pm
1 stop8h 45m
Oakland
Tue 6/9
5:55 am-9:30 pm
1 stop12h 35m
$602
PortlandOakland
PWM - OAK
PWMOAK
Portland
Thu 7/9
11:47 am-11:50 am
2 stops27h 03m
Oakland
Mon 7/20
6:00 am-11:14 pm
2 stops14h 14m
$683
Cheapest one-way
Quickest one-way
PortlandOakland
PWM - OAK
PWMOAK
Portland
Thu 10/8
6:30 am-12:35 pm
1 stop9h 05m
$209
PortlandOakland
PWM - OAK
PWMOAK
Portland
Mon 6/15
3:10 pm-12:15 am
2 stops12h 05m
$214
Showing 1-10 of 12 resultsSorted by cheapest first
Compare providers for flights from Portland to Oakland
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 Portland to Oakland in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy1 star | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland, Maine-Oakland, California flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Oakland, California flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Oakland, California flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Oakland, California flights, Cheapflights users trust FlightHub the most. FlightHub 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 Portland, Maine-Oakland, California 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 Portland to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Portland with our price prediction graph.
PWM-OAK
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.
Related info for your journey
Find useful and relevant information for your journey from Portland to Oakland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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