PWM - SJO

$298 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 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

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 21% 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
$436
Typical prices: $392-$501
American Airlines
Fri 10/9Sat 10/17
PWM - SJO • 2 stops
Cheapest one-way
$298
United Airlines
Mon 8/10
PWM - SJO • 2 stops
Top airlines
Cheapest • from $436 (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 • 75% 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
7:20 pm - 1:00 pm
PWM
-
SJO
19h 40m
2 stops
American Airlines Logo
12:57 pm - 11:33 am
SJO
-
PWM
20h 36m
2 stops
$436American Airlines
Thu, Sep 3 - Fri, Sep 11
American Airlines Logo
6:46 pm - 1:52 pm
PWM
-
SJO
21h 06m
2 stops
American Airlines Logo
2:57 pm - 12:40 pm
SJO
-
PWM
19h 43m
2 stops
$461American Airlines
Thu, Sep 3 - Fri, Sep 11
Delta Logo
6:05 am - 11:49 am
PWM
-
SJO
7h 44m
1 stop
Delta Logo
1:19 pm - 11:30 pm
SJO
-
PWM
8h 11m
1 stop
$495Delta
Thu, Sep 3 - Fri, Sep 11
American Airlines Logo
7:05 am - 12:26 pm
PWM
-
SJO
7h 21m
1 stop
American Airlines Logo
2:57 pm - 12:40 pm
SJO
-
PWM
19h 43m
2 stops
$498American 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
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
6:46 pm - 12:03 pm
PWM
-
SJO
19h 17m
2 stops
American Airlines Logo
2:56 pm - 12:40 pm
SJO
-
PWM
19h 44m
2 stops
$511American Airlines
Mon, Aug 17 - Mon, Aug 24
American Airlines Logo
6:46 pm - 12:03 pm
PWM
-
SJO
19h 17m
2 stops
American Airlines Logo
1:29 pm - 12:40 pm
SJO
-
PWM
21h 11m
1 stop
$521American Airlines
Thu, Sep 3 - Fri, Sep 11
United Airlines Logo
6:00 am - 11:38 am
PWM
-
SJO
7h 38m
1 stop
United Airlines Logo
12:44 pm - 9:08 am
SJO
-
PWM
18h 24m
1 stop
$539United Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
7:43 pm - 7:39 pm
PWM
-
SJO
25h 56m
2 stops
United Airlines Logo
12:55 pm - 11:23 pm
SJO
-
PWM
8h 28m
1 stop
$561United Airlines
Mon, Oct 26 - Thu, Oct 29
United Airlines Logo
7:43 pm - 7:39 pm
PWM
-
SJO
25h 56m
2 stops
United Airlines Logo
1:25 pm - 2:20 pm
SJO
-
PWM
22h 55m
2 stops
$571United 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 $436 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 4246 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

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.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

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.

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.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

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.

Flight was delayed…once landed at ORD, no gates were available so made us wait for 56 minutes after we landed to let us out of the aircraft!

Entertainment system did not function. USB ports did not function. Wi-Fi did not function. Terrible trifecta…

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

My flight was delayed twice. The first time because of “plane maintenance” and the second because the previous flight who supposedly “arrived early” took an obnoxiously long time to get off the plane. Total delay was over an hour for no reason. Not to mention your airline repeatedly changed our gate from one end of the terminal to the other. Not very happy about this experience. My previous flights with American haven’t had this many issues.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

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