PWM - SJO

$129 Find Cheap Flights from Portland to San José

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 5/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to San José

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to San José, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Portland to San José, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
$305
Typical prices: $592-$1,044
American Airlines
Thu 4/30Thu 5/7
PWM - SJO • 2 stops
Cheapest one-way
$129
Typical prices: $148-$347
American Airlines
Tue 5/5
PWM - SJO • 2 stops
Top airlines
American Airlines
Cheapest • from $305 (round-trip)
Southwest
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
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
Insights
Insights
Top layover airports
New York (JFK)
Cheapest • Avg $394 (round-trip)
Fort Lauderdale (FLL)
Shortest trip • 7h 56m (one-way)
Insights
Insights
Insights
Insights
When to travel
July
Cheapest • 68% price drop
January
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
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

Thu, Apr 30 - Thu, May 7
American Airlines Logo
6:00 am - 7:07 pm
PWM
-
SJO
15h 07m
2 stops
American Airlines Logo
2:22 pm - 11:15 am
SJO
-
PWM
18h 53m
2 stops
$305American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
6:01 pm - 11:25 am
PWM
-
SJO
19h 24m
2 stops
American Airlines Logo
6:30 am - 11:54 pm
SJO
-
PWM
15h 24m
2 stops
$376American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
1:18 pm - 11:25 am
PWM
-
SJO
24h 07m
1 stop
American Airlines Logo
12:35 pm - 10:46 pm
SJO
-
PWM
8h 11m
1 stop
$378American Airlines
Mon, Apr 20 - Tue, Apr 28
American Airlines Logo
6:01 pm - 11:07 am
PWM
-
SJO
19h 06m
2 stops
American Airlines Logo
12:10 pm - 11:15 am
SJO
-
PWM
21h 05m
2 stops
$379American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
1:18 pm - 11:25 am
PWM
-
SJO
24h 07m
1 stop
American Airlines Logo
12:10 pm - 12:38 pm
SJO
-
PWM
22h 28m
2 stops
$383American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
1:18 pm - 11:25 am
PWM
-
SJO
24h 07m
1 stop
American Airlines Logo
6:30 am - 11:27 pm
SJO
-
PWM
14h 57m
2 stops
$386American Airlines
Mon, Apr 20 - Tue, Apr 28
American Airlines Logo
6:01 pm - 11:07 am
PWM
-
SJO
19h 06m
2 stops
American Airlines Logo
12:10 pm - 11:15 am
SJO
-
PWM
21h 05m
2 stops
$424American Airlines
Tue, May 5 - Mon, May 11
JetBlue Logo
6:00 am - 10:14 pm
PWM
-
SJO
18h 14m
1 stop
JetBlue Logo
11:59 pm - 11:36 pm
SJO
-
PWM
21h 37m
1 stop
$427JetBlue
Mon, Apr 20 - Tue, Apr 28
American Airlines Logo
6:01 pm - 11:07 am
PWM
-
SJO
19h 06m
2 stops
American Airlines Logo
12:10 pm - 11:15 am
SJO
-
PWM
21h 05m
2 stops
$433American Airlines
Tue, May 5 - Mon, May 11
American Airlines Logo
1:18 pm - 11:25 am
PWM
-
SJO
24h 07m
1 stop
American Airlines Logo
12:35 pm - 10:46 pm
SJO
-
PWM
8h 11m
1 stop
$435American 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 April.

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 $224 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $1,778 and $979 respectively.

Good to know

Low seasonAugust
Cheapest flight$129
Best time to beat the crowds with an average 31% drop in price.
Most popular time to fly and prices are also 48% 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 3 days, the lowest price for a flight from Portland to San José was $129 for a one-way ticket and $305 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?

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

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

    The two airlines most popular with KAYAK users for flights from Portland to San José are Southwest and Delta. With an average price for the route of $798 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $667 and an overall rating of 7.9.

  • 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 4 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.
8.0
SouthwestOverall score based on 4311 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

8.0 ExcellentAnonymous, Mar 2026
MCO - IND
Read more Southwest reviews

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The travel company that you have on your site did me so wrong. I don’t know how it happened, but they put my son‘s name on my plane ticket flying to Vietnam. Along with his birthday. They would not have let me fly from Fort Myers to Ho Chi Minh City. I don’t think that I can ever use your service again. I typed my information into the browser along with my passport number and four days before I’m leaving I have to quickly search another ticket to fly out here.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

The flight was delayed so we were dead tired, and after that the turbulence was horrible. I was very scared.

It’s always a great time flying with united airlines.

Good flight. Efficient boarding and competent flight crew. No problems until we arrived at our destination gate. We were early so there was an aircraft at the gate that had to move before we could pull in. Then, due to the type of aircraft we flew, the cabin door could not be opened until some luggage from the cargo bay was offloaded to preserve center of gravity characteristics. So, that further delayed deplaning. Despite being 20 minutes early on landing, we ended up being 5 to 10 minutes late after all the delays.

Everything went well except the turbulence what no one have a control of but pilot and crew handled very good!

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

The baggage claim experience was poor. The plane crew and the AA app said that checked baggage in CLT would be at carousel 7 but the sign at Baggage Claim said carousel 1. The carousel 1 sign had the correct flight # listed above the belt. But the luggage never came. I went to an AA baggage claim office after about 1 hour and the clerk directed me to another AA room that was poorly marked, with a closed door and no obvious way to know what to do. Finally someone opened the door and my bag was inside. The clerk was totally unable to explain why.

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Forced to check bags. Crew uninterested in collecting trash. Unclean seats.

why would I bother with this airline and pick seats when I am asked to move for a weight imbalance

Flight pulled out on time but sat on runway for 30 mins. It was extremely cold in the aircraft despite wearing a winter coat. Surprisingly they had a vegetarian meal but could have some better snack choices for a 8 hour flight.

We had a male flight attendant who was super attentive and wonderful! Very professional. I have both gluten and dairy intolerance, and was only able to get a gluten free part, and not the dairy free part of the meal. Easy to order ahead of time and I appreciate being able to do that.

Snow delayed boarding several times, which I understand happens. Issue I had was that after we did board, pilot told us we were going to roll out to be de-iced, then on our way. We were de-iced once, taxied to the tarmac and then stopped. Sat for another 30 minutes or so, the another de-icing. Then we rolled out to a parking spot, only to sit for another hour due to a traffic stop in DCA, which I'm confident they knew would happen before we boarded. Pilot gave no updates other than we had to hold, attendants did speak to the crew, but when asked, said the pilot would be updating us. We on the ground in the plane waiting for over 2 hours. They did communicate that bathrooms would be open, but no other news until we left. Would have been better to be up front about status.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

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

Information on your arrival and departure airports