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$205+ Cheap flights from San Jose, CA to Portland, ME (SJC - 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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — PWM
Apr 11 — Apr 181
Sat 4/11
Sat 4/18
1 adult, Economy
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Cheap flight deals from San Jose to Portland

Cheapest flights from San Jose to Portland
Explore the most affordable flight options available from San Jose to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 12, 2026.

This United Airlines deal was found by Cheapflights users on 3/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:45 am
SJC
-
PWM
2 stops11h 44m
United Airlines
Fri 5/84:50 pm
PWM
-
SJC
1 stop9h 06m
United Airlines
Deal found 3/11$422
This Southwest deal was found by Cheapflights users on 3/9. 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 5/310:45 am
SJC
-
PWM
2 stops10h 20m
Southwest
Sat 5/95:40 am
PWM
-
SJC
2 stops11h 45m
Southwest
Deal found 3/9$433
This Delta deal was found by Cheapflights users on 3/7. 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.
Tue 4/710:50 pm
SJC
-
PWM
2 stops10h 19m
Delta
Thu 4/95:23 am
PWM
-
SJC
1 stop9h 45m
Delta
Deal found 3/7$444
This Southwest deal was found by Cheapflights users on 3/9. 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 4/309:00 am
SJC
-
PWM
2 stops11h 25m
Southwest
Fri 5/85:30 am
PWM
-
SJC
1 stop9h 50m
Southwest
Deal found 3/9$448
This Southwest deal was found by Cheapflights users on 3/8. 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 5/169:20 am
SJC
-
PWM
2 stops10h 50m
Southwest
Mon 5/182:50 pm
PWM
-
SJC
2 stops12h 05m
Southwest
Deal found 3/8$450
This Southwest deal was found by Cheapflights users on 3/10. 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 6/1310:05 am
SJC
-
PWM
2 stops10h 35m
Southwest
Sat 8/155:40 am
PWM
-
SJC
1 stop8h 50m
Southwest
Deal found 3/10$452
This Southwest deal was found by Cheapflights users on 3/11. 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 5/2810:25 am
SJC
-
PWM
2 stops10h 00m
Southwest
Sun 5/315:30 am
PWM
-
SJC
1 stop15h 35m
Southwest
Deal found 3/11$456
This Southwest deal was found by Cheapflights users on 3/9. 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 5/19:10 am
SJC
-
PWM
2 stops11h 15m
Southwest
Fri 5/85:30 am
PWM
-
SJC
2 stops10h 50m
Southwest
Deal found 3/9$457
This Delta deal was found by Cheapflights users on 3/9. 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 6/312:12 pm
SJC
-
PWM
1 stop7h 57m
Delta
Sun 6/76:00 am
PWM
-
SJC
2 stops14h 14m
Delta
Deal found 3/9$464

Find flight deals from San Jose to Portland

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) 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 March 12, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$422
(United Airlines)

One-way from

$205
(Southwest)
Provider with most accurate pricing for San Jose-Portland flight deals.
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Provider most trusted by Cheapflights users for San Jose-Portland flights.
Search Deals
From San Jose to Portland
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One-way flight from San Jose to Portland
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Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose 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 March 12, 2026.
Use the filters below to find and compare flights from San Jose to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JosePortland

SJC - PWM

SJCPWM

San Jose

Fri 5/1

9:10 am-11:25 pm

2 stops11h 15m

Portland

Fri 5/8

5:30 am-1:20 pm

2 stops10h 50m

$457

San JosePortland

SJC - PWM

SJCPWM

San Jose

Tue 3/24

9:50 pm-11:55 am

1 stop11h 05m

Portland

Tue 3/31

4:30 pm-9:45 pm

1 stop8h 15m

$472

San JosePortland

SJC - PWM

SJCPWM

San Jose

Tue 5/5

6:30 am-11:59 pm

2 stops14h 29m

Portland

Wed 5/6

6:00 am-6:31 pm

2 stops15h 31m

$477

San JosePortland

SJC - PWM

SJCPWM

San Jose

Tue 4/7

10:50 pm-12:09 pm

2 stops10h 19m

Portland

Wed 4/8

4:48 pm-8:16 am

2 stops18h 28m

$505

San JosePortland

SJC - PWM

SJCPWM

San Jose

Sun 6/14

9:40 pm-9:45 am

1 stop9h 05m

Portland

Sat 6/20

8:25 am-8:00 pm

1 stop14h 35m

$530
Quickest round-trip

San JosePortland

SJC - PWM

SJCPWM

San Jose

Mon 6/29

12:45 pm-11:53 pm

1 stop8h 08m

Portland

Tue 7/7

4:50 pm-9:48 pm

1 stop7h 58m

$543
Cheapest one-way

San JosePortland

SJC - PWM

SJCPWM

San Jose

Thu 6/4

10:25 am-12:05 am

2 stops10h 40m

$205
Quickest one-way

San JosePortland

SJC - PWM

SJCPWM

San Jose

Tue 6/16

9:40 pm-9:55 am

1 stop9h 15m

$224

San JosePortland

SJC - PWM

SJCPWM

San Jose

Wed 8/12

7:11 pm-11:12 am

2 stops13h 01m

$229

San JosePortland

SJC - PWM

SJCPWM

San Jose

Tue 6/16

6:00 am-10:47 pm

2 stops13h 47m

$238

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/11

Showing 1-10 of 16 resultsSorted by cheapest first
1
2
  • Most accurate provider: When it comes to deals on San Jose, 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 San Jose, California-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose, California-Portland, Maine 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 San Jose, 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 San Jose to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from San Jose 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 San Jose to Portland

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

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Portland, Maine (average of $118). Flying from San Jose, California to Portland, Maine in January is currently the most expensive (average of $189). 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 March 12, 2026.
Read reviews from past customers who have flown Southwest,Delta, andAmerican Airlines from San Jose 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
4,319 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Southwest
8.0
Very good
4,319 reviews
Southwest
8.0
Very good
4,319 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
Delta
7.9
Good
8,286 reviews
Southwest
8.0
Very good
4,319 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.
American Airlines
7.1
Good
11,432 reviews
Southwest
8.0
Very good
4,319 reviews

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Overall

8.0

Food

7.0

Reviews

1 / 20
10.0
Excellent

William Drew,Nov 2025

SJC - HNL

Flight crew was amazing! Usually they're very good on Southwest, but this crew went above and beyond. I have never ever seen so many rounds of drink service on a flight before.

Related info for your journey

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

  • How long is the flight from San Jose, California to Portland, Maine?

    A quick flight from San Jose, California to Portland, Maine can take about 11h 15m. Southwest provides one of the quickest options available for as low as $457. There are 2700 mi between San Jose, California and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from San Jose, California to Portland, Maine round-trip?

    Flying on American Airlines is currently your cheapest option to Portland, Maine, with prices starting at $276. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $276 and $423, respectively.

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

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

  • How can I find direct flights from San Jose to Portland?

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

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

    Yes. Cheapflights offers flight deals from San Jose 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 San Jose, California to Portland, Maine?

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Portland, Maine (average of $118). Flying from San Jose, California to Portland, Maine in January is currently the most expensive (average of $189). 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
North Conway
Brunswick
Auburn
Lewiston
Conway

Browse thousands of different options on Cheapflights for your next trip

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Top 3 airlines flying from San Jose to Portland

Discover the top 3 airlines that operate flights from San Jose 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 March 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$276Average$445FlexibilityNo cancel feeOn-time71%
DeltaCheapest$276Average$488FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$423Average$552FlexibilityNo cancel feeOn-time63%

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