PWM - SJO

$345 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 5/10. 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

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
$345
Typical prices: $616-$513
American Airlines
Tue 10/27Tue 11/3
PWM - SJO • 2 stops
Cheapest one-way
$161
Typical prices: $148-$345
United Airlines
Sun 5/10
PWM - SJO • 2 stops
Top airlines
Cheapest • from $345 (round-trip)
Best reviews • 7.9 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 • 46% 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

Tue, Oct 27 - Tue, Nov 3
American Airlines Logo
7:20 pm - 11:05 am
PWM
-
SJO
17h 45m
2 stops
American Airlines Logo
1:09 pm - 11:38 pm
SJO
-
PWM
9h 29m
2 stops
$345American Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:20 pm - 1:00 pm
PWM
-
SJO
19h 40m
2 stops
American Airlines Logo
1:05 pm - 1:22 pm
SJO
-
PWM
22h 17m
2 stops
$404American Airlines
Tue, Oct 27 - Tue, Nov 3
United Airlines Logo
6:00 am - 11:42 am
PWM
-
SJO
7h 42m
1 stop
United Airlines Logo
11:28 pm - 1:38 pm
SJO
-
PWM
13h 10m
1 stop
$406United Airlines
Fri, Oct 9 - Sat, Oct 17
American Airlines Logo
7:20 pm - 11:05 am
PWM
-
SJO
17h 45m
2 stops
American Airlines Logo
1:05 pm - 12:32 pm
SJO
-
PWM
21h 27m
2 stops
$413American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
5:58 pm - 11:50 am
PWM
-
SJO
19h 52m
2 stops
American Airlines Logo
12:50 pm - 12:35 pm
SJO
-
PWM
21h 45m
2 stops
$420American Airlines
Fri, Sep 18 - Wed, Oct 7
American Airlines Logo
7:20 pm - 11:05 am
PWM
-
SJO
17h 45m
2 stops
American Airlines Logo
1:05 pm - 11:54 am
SJO
-
PWM
20h 49m
2 stops
$449American Airlines
Tue, Jul 21 - Tue, Jul 28
American Airlines Logo
6:00 pm - 1:11 pm
PWM
-
SJO
21h 11m
2 stops
American Airlines Logo
2:00 pm - 5:10 pm
SJO
-
PWM
25h 10m
1 stop
$459American Airlines
Tue, Oct 27 - Tue, Nov 3
Multiple Airlines Logo
6:30 am - 11:45 am
PWM
-
SJO
31h 15m
3 stops
Multiple Airlines Logo
9:45 am - 11:43 pm
SJO
-
PWM
36h 58m
2 stops
$500Multiple Airlines
Tue, Sep 29 - Thu, Oct 1
United Airlines Logo
6:00 am - 11:38 am
PWM
-
SJO
7h 38m
1 stop
United Airlines Logo
12:44 pm - 11:27 pm
SJO
-
PWM
8h 43m
1 stop
$501United Airlines
Tue, Sep 29 - Thu, Oct 1
United Airlines Logo
6:00 am - 7:37 pm
PWM
-
SJO
15h 37m
2 stops
United Airlines Logo
7:55 am - 11:27 pm
SJO
-
PWM
13h 32m
2 stops
$506United 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 January, where tickets cost $362 (return) on average. On the other hand, the most expensive months are December and March, where the average cost of round-trip tickets is $1,778 and $703 respectively.

Good to know

Low seasonAugust
Cheapest flight$161
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly and prices are also 47% 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 $161 for a one-way ticket and $345 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 $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.
7.9
SouthwestOverall score based on 4305 reviews
8.6Crew
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

2.0 MediocreJoshua, May 2026
TPA - LAS
Read more Southwest reviews

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Overall a good experience, but no wifi available for free or for purchase and we got wet from condensation or other water source during descent.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

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

Information on your arrival and departure airports