PWM - SJO

$298 Find Cheap Flights from Portland to San José - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Portland to San José departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$394
Typical prices: $484-$616
United Airlines
Fri 10/30Fri 11/6
PWM - SJO • 1 stop
Cheapest one-way
$298
United Airlines
Mon 8/10
PWM - SJO • 2 stops
Top airlines
Cheapest • from $394 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
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Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Portland and San José. You'll need at least 1 connection.
Insights
Insights
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Insights
Top layover airports
Cheapest • Avg $464 (round-trip)
Shortest trip • 7h 56m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 75% price drop
Most popular
Good to know
Good to know
+1
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Good to know
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We hope you love your trip to San José!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to San José (PWM-SJO)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to San José that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Portland to San José

Fri, Oct 30 - Fri, Nov 6
United Airlines Logo
6:00 am - 6:53 pm
PWM
-
SJO
14h 53m
1 stop
United Airlines Logo
1:55 pm - 11:23 pm
SJO
-
PWM
8h 28m
1 stop
$394United Airlines
Tue, Jul 14 - Fri, Jul 17
American Airlines Logo
6:01 pm - 1:11 pm
PWM
-
SJO
21h 10m
2 stops
American Airlines Logo
6:00 am - 12:43 am
SJO
-
PWM
16h 43m
2 stops
$474American Airlines
Fri, Oct 2 - Wed, Oct 14
Southwest Logo
6:30 am - 7:40 pm
PWM
-
SJO
15h 10m
2 stops
Southwest Logo
9:00 am - 10:35 pm
SJO
-
PWM
11h 35m
2 stops
$475Southwest
Fri, Oct 30 - Fri, Nov 6
Multiple Airlines Logo
6:30 am - 9:35 am
PWM
-
SJO
29h 05m
2 stops
Multiple Airlines Logo
4:15 pm - 11:43 pm
SJO
-
PWM
30h 28m
2 stops
$487Multiple Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:24 pm - 12:00 pm
PWM
-
SJO
18h 36m
2 stops
American Airlines Logo
1:00 pm - 10:22 am
SJO
-
PWM
19h 22m
2 stops
$506American Airlines
Fri, Oct 2 - Wed, Oct 14
Delta Logo
6:00 am - 11:54 am
PWM
-
SJO
7h 54m
1 stop
Delta Logo
1:23 pm - 11:36 pm
SJO
-
PWM
8h 13m
1 stop
$508Delta
Thu, Oct 29 - Thu, Nov 5
Delta Logo
6:00 am - 11:58 am
PWM
-
SJO
7h 58m
1 stop
Delta Logo
2:23 pm - 1:22 pm
SJO
-
PWM
21h 59m
2 stops
$513Delta
Thu, Oct 29 - Fri, Nov 6
United Airlines Logo
6:00 am - 6:53 pm
PWM
-
SJO
14h 53m
1 stop
United Airlines Logo
11:28 pm - 4:09 pm
SJO
-
PWM
15h 41m
1 stop
$514United Airlines
Thu, Oct 29 - Fri, Nov 6
United Airlines Logo
6:00 am - 7:39 pm
PWM
-
SJO
15h 39m
2 stops
United Airlines Logo
1:55 pm - 11:23 pm
SJO
-
PWM
8h 28m
1 stop
$519United Airlines
Fri, Oct 2 - Tue, Oct 13
United Airlines Logo
6:00 am - 7:37 pm
PWM
-
SJO
15h 37m
2 stops
United Airlines Logo
7:55 am - 9:08 am
SJO
-
PWM
23h 13m
2 stops
$529United Airlines
Booking Insights

KAYAK's insights & trends for Portland to San José flights

Get data-powered insights and trends into flights from Portland to San José to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Portland, Maine to San José?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Portland, Maine to San José departing in October.

What is the cheapest month to fly from Portland to San José?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to San José, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to San José is July, where tickets cost $178 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $2,191 and $755 respectively.

Good to know

Low seasonAugust
Cheapest flight$298
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly and prices are also 51% lower on average.
Flight from Portland to San José

When to book flights from Portland to San José

Are your dates flexible? Find out the best times to travel from Portland to San José based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Portland to San José

  • What is the cheapest flight from Portland to San José?

    In the last 5 days, the lowest price for a flight from Portland to San José was $298 for a one-way ticket and $394 for a round-trip.

  • Do I need a passport to fly between Portland and San José?

    Yes, you'll most likely have to show a valid passport before boarding the plane in Portland and on arrival in San José.

  • Which airports will I be using when flying from Portland to San José?

    When flying out of Portland you will be using Portland. You will be landing at San José, also known as San José Juan Santamaria Intl.

  • Which aircraft models fly most regularly from Portland to San José?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Portland to San José?

    Star Alliance, and oneworld are the airline alliances operating flights between Portland and San José, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Portland to San José, Southwest or United Airlines?

    The two airlines most popular with KAYAK users for flights from Portland to San José are Southwest and United Airlines. With an average price for the route of $798 and an overall rating of 7.9, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $716 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Portland to San José?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Portland to San José.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to San José?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San José from Portland is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Portland to San José?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to San José with an airline and back to Portland with another airline. Booking your flights between Portland and SJO can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Portland to San José?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to San José from Portland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Portland to San José

 
See real verified KAYAK customer reviews for airlines flying from Portland to San José. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to San José? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

The flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Staff could’ve been a little more cordial. The men were much more friendlier than the women. My daughter and I also missed the 2nd to last meal as we were sleeping but that is on us.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

Both my flight where delayed Had 25min to make it to my transfer flight

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

I had very little time to change planes originally in Denver after my flight from Omaha. I had an hour and a half layover in Denver originally and my flight leaving Omaha was delayed an hour because they had to change a tire, which I can understand. When I reached Denver my other flight was late, fortunately, but I still had only 10 minutes to run about a mile through the airport to get to my flight. Again, fortunately, I am a healthy 71-year-old and was able to accomplish this feat. However, the stress was more than necessary to bear.

I found the seats ergonomically uncomfortable forcing the body to seat slightly hunched. For a short flight I worked on adjustments but for a longer flight, it would be difficult.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Crew was great! Food sub-bar, tepid & flavorless. No snack options on trans-atlantic flight. Premium Economy seats ok, leg rest wouldn’t stay in place.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

The flight attendant was very polite and attentive. The food was good.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

A much better flight than our previous. The flight attendant took care of us and regularly checked in to see if we needed anything. Brought us drinks prior to the departure and then a couple more times. Totally makes the difference in how you travel when the crew is checking on their passengers. Great job on this leg of our trip.

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

I just for my TSA. So security line is short and upgraded to one group up. I do think the ground crew should learn new way of boarding - the passengers sitting in higher number seat should board first to prevent traffic jam.

Everything you need to know for your flight from Portland to San José

Information on your arrival and departure airports