PWM - SJO

$419 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 6/7. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$419
Typical prices: $501-$460
American Airlines
Fri 10/9Sat 10/17
PWM - SJO • 2 stops
Cheapest one-way
$226
Typical prices: $213-$286
United Airlines
Sun 6/7
PWM - SJO • 2 stops
Top airlines
Cheapest • from $419 (round-trip)
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
Cheapest • Avg $464 (round-trip)
Shortest trip • 7h 56m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 66% price drop
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

Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
2:55 pm - 11:05 am
PWM
-
SJO
22h 10m
2 stops
American Airlines Logo
2:45 pm - 1:22 pm
SJO
-
PWM
20h 37m
2 stops
$419American Airlines
Wed, Jun 24 - Tue, Jul 7
Multiple Airlines Logo
2:20 pm - 10:11 am
PWM
-
SJO
21h 51m
2 stops
Multiple Airlines Logo
12:30 am - 9:41 pm
SJO
-
PWM
19h 11m
2 stops
$549Multiple Airlines
Tue, Jun 30 - Mon, Jul 6
American Airlines Logo
5:58 pm - 1:08 pm
PWM
-
SJO
21h 10m
2 stops
American Airlines Logo
3:37 pm - 1:40 pm
SJO
-
PWM
20h 03m
2 stops
$568American Airlines
Wed, Jun 24 - Wed, Jul 8
Avianca Logo
2:20 pm - 10:11 am
PWM
-
SJO
21h 51m
2 stops
Avianca Logo
7:15 am - 11:30 pm
SJO
-
PWM
14h 15m
1 stop
$580Avianca
Thu, Jun 11 - Fri, Jun 19
United Airlines Logo
3:16 pm - 10:11 am
PWM
-
SJO
20h 55m
2 stops
United Airlines Logo
7:55 am - 11:51 pm
SJO
-
PWM
37h 56m
2 stops
$583United Airlines
Wed, Jun 24 - Tue, Jul 7
United Airlines Logo
5:15 am - 10:11 am
PWM
-
SJO
30h 56m
3 stops
United Airlines Logo
12:30 am - 9:41 pm
SJO
-
PWM
19h 11m
2 stops
$595United Airlines
Wed, Jul 29 - Tue, Aug 4
United Airlines Logo
5:15 am - 10:11 am
PWM
-
SJO
30h 56m
3 stops
United Airlines Logo
12:30 am - 11:30 pm
SJO
-
PWM
21h 00m
2 stops
$632United Airlines
Wed, Jul 29 - Wed, Aug 5
Multiple Airlines Logo
2:40 pm - 8:30 am
PWM
-
SJO
19h 50m
2 stops
Multiple Airlines Logo
4:35 pm - 1:45 pm
SJO
-
PWM
19h 10m
2 stops
$644Multiple Airlines
Tue, Jun 30 - Sun, Jul 5
United Airlines Logo
5:15 am - 10:11 am
PWM
-
SJO
30h 56m
3 stops
United Airlines Logo
12:30 am - 7:27 pm
SJO
-
PWM
40h 57m
2 stops
$649United Airlines
Fri, Oct 9 - Sat, Oct 17
United Airlines Logo
6:00 am - 11:38 am
PWM
-
SJO
7h 38m
1 stop
United Airlines Logo
7:55 am - 10:46 am
SJO
-
PWM
24h 51m
2 stops
$666United 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 $224 (return) on average. On the other hand, the most expensive months are December and June, where the average cost of round-trip tickets is $1,725 and $716 respectively.

Good to know

Low seasonAugust
Cheapest flight$226
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 46% 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 $226 for a one-way ticket and $419 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 8.0, Southwest is the most popular choice. United Airlines is also a great choice for the route, with an average price of $703 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.
8.0
SouthwestOverall score based on 4257 reviews
8.6Crew
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

I don't know why flying out of Sarasota requires two plane changes.

10.0 ExcellentJohn, Jun 2026
DAL - ABQ
Read more Southwest reviews

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

Boarded early, left early, arrived 40 mins early! A win win for me!

New plane was lovely. Crew customer service is always lax but expected. Kraft on time and arrived safely.

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

It was a short flight so I was expecting too much

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

I felt scammed. The priced advertised was different than what I paid. I paid the whole some online. I then got a call 20 minutes later saying I need to paid 70 more person. She said the price online is not the guaranteed price.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

The flight from Dallas to Tokyo was not on Japan Airlines. It was on American Airlines. Very disappointed that we did not fly on Japan Airlines. Will not be using you liars again. I’ll just book direct from the airline next time. Wish you could make this right and has us fly on Japan Air when heading back home to the US.

The Mario was so helpful and provided amazing customer service however l have being waiting for a callback for almost a week now and have not heard anything further after l informed them l wanted to change my date of traveling because of my hospital appointment even send them proof and l was unable to use manag your booking on their website is a bit frustrating and l would appreciate an update on My request as soon as possible. And have called them times without numbers no response

They made nearly everyone check their bag because the overhead bins are way too small. Extremely inconvenient

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

Was put into a seat right behind the toilet that had no entertainment possible but did have plenty of leg room over noisy part of plane.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Movies on my phone are great. It would be nice to have a gluten free snack option.

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

The flight was peaceful, just s slight turbulence, pilots and crews were all nice and made a great job! Arrived safely in the Philippines. Thank you ya’ll!

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

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

Information on your arrival and departure airports