$233 Find Cheap Flights from Portland to Puerto Rico

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 Puerto Rico departing on 10/20. 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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Cheap Flights from Portland to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Aguadilla
Aguadilla2 stops$550
Culebra
Culebra2 stops$1,558
Aguadilla
Aguadilla2 stops$550
Culebra
Culebra2 stops$1,558

Book Cheap Portland to Puerto Rico Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Portland to Puerto Rico 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 Puerto Rico

Thu, Aug 20 - Mon, Aug 24
Southwest Logo
6:05 am - 10:15 pm
PDX
-
SJU
13h 10m
2 stops
Southwest Logo
5:00 am - 3:00 pm
SJU
-
PDX
13h 00m
2 stops
$466Southwest
Thu, Aug 27 - Sun, Aug 30
Southwest Logo
10:45 pm - 2:30 pm
PDX
-
SJU
12h 45m
1 stop
Southwest Logo
5:30 am - 12:45 pm
SJU
-
PDX
10h 15m
1 stop
$498Southwest
Sat, Sep 26 - Sat, Oct 31
Delta Logo
5:05 pm - 11:48 am
PDX
-
SJU
15h 43m
2 stops
Delta Logo
12:46 pm - 10:26 pm
SJU
-
PDX
12h 40m
1 stop
$530Delta
Wed, Aug 12 - Fri, Aug 21
American Airlines Logo
6:00 am - 11:07 pm
PDX
-
SJU
14h 07m
1 stop
American Airlines Logo
3:44 pm - 11:07 pm
SJU
-
PDX
10h 23m
1 stop
$535American Airlines
Tue, Jul 28 - Fri, Aug 14
American Airlines Logo
6:07 am - 11:48 pm
PDX
-
SJU
14h 41m
1 stop
American Airlines Logo
12:59 am - 5:51 pm
SJU
-
PDX
19h 52m
1 stop
$548American Airlines
Wed, Aug 19 - Tue, Aug 25
United Airlines Logo
5:00 am - 11:09 pm
PDX
-
BQN
15h 09m
2 stops
United Airlines Logo
12:15 am - 9:50 am
BQN
-
PDX
12h 35m
1 stop
$550United Airlines
Wed, Jul 8 - Thu, Jul 16
American Airlines Logo
5:49 am - 10:59 pm
PDX
-
SJU
14h 10m
1 stop
American Airlines Logo
7:00 am - 11:30 pm
SJU
-
PDX
19h 30m
1 stop
$553American Airlines
Tue, Jul 28 - Mon, Aug 3
American Airlines Logo
6:07 am - 11:48 pm
PDX
-
SJU
14h 41m
1 stop
American Airlines Logo
7:00 am - 11:30 pm
SJU
-
PDX
19h 30m
1 stop
$554American Airlines
Tue, Jul 28 - Mon, Aug 3
American Airlines Logo
6:07 am - 11:48 pm
PDX
-
SJU
14h 41m
1 stop
American Airlines Logo
7:00 am - 11:30 pm
SJU
-
PDX
19h 30m
1 stop
$556American Airlines
Wed, Aug 19 - Tue, Aug 25
United Airlines Logo
5:00 am - 11:09 pm
PDX
-
BQN
15h 09m
2 stops
United Airlines Logo
12:15 am - 11:28 am
BQN
-
PDX
14h 13m
2 stops
$575United Airlines
Booking Insights

KAYAK's insights & trends for Portland to Puerto Rico flights

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

What is the cheapest month to fly from Portland to Puerto Rico?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Puerto Rico, 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 Puerto Rico is August, when tickets cost $185 (return) on average. On the other hand, the most expensive months are May and January, when the average cost of round-trip tickets is $376 and $307 respectively.

How far in advance should I book a flight from Portland to Puerto Rico?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Puerto Rico, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Puerto Rico, you should book around 4 weeks before departure, which saves you about 25% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$233
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 17% increase in price.
Flight from Portland to San Juan

FAQs - booking Puerto Rico flights

  • Do you require a visa to fly from Portland to Puerto Rico?

    No. You do not require a visa for you to fly from Portland to Puerto Rico if you are a US Citizen. Trips to Puerto Rico from Portland are considered domestic, and travelers only have to produce government issued-ID or driver’s license.

  • Which airline should I use when flying to Puerto Rico from Portland with my kids?

    Among the airlines flying from Portland to Puerto Rico, American Airlines have the best amenities for travelers with kids. The airline offers unless kid-friendly entertainment throughout the entire journey. Additionally, all the cabins have spacious seats with extra legroom, giving you and your kids the comfort you deserve.

  • Are there direct flights from Portland to Puerto Rico?

    Yes. All airlines flying to Puerto Rico from Portland, including American Airlines, Frontier, Spirit, Delta Airlines, and United Airlines, all offer nonstop daily flights. With these, it is easier to fly along this route from Portland, especially if you have to attend to something urgent in Puerto Rico.

  • How can I get to Carolina city center from San Juan Airport?

    Taxis offer the fastest and most convenient means of transport from San Juan Airport to the Carolina city center. In light traffic, a taxi ride to the city center from the airport takes about 25 minutes. If you want to enjoy self-drive to the city or other destinations in the city, consider renting a car once you deplane at San Juan Airport.

  • How does KAYAK find such low prices on flights from Portland to Puerto Rico?

    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 Puerto Rico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Puerto Rico 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 Puerto Rico?

    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 from Portland to Puerto Rico with an airline and back with another airline.

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

    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 from Portland to Puerto Rico up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Puerto Rico

  • Most travelers flying from Portland to Puerto Rico prefer using Portland International Airport (PDX) as the departure airport. Compared to other airports in the city, it is easier to access PDX from various points in the city. Additionally, having the highest number of daily flights to Puerto Rico, travelers can catch up with a flight from Portland International Airport that is convenient to their schedule.
  • You will connect to Portland International Airport from downtown Portland using various transport options. MAX Light rail, which has a station at the airport’s lower level, is the most convenient and cost-effective means of transport. It takes about 35 minutes to arrive at the airport from downtown. Other available means of transport include taxis, shuttles, and ride-share services.
  • If you want to catch up with the earliest flight from Portland to Puerto Rico, which departs from Portland International Airport at around 5:05 am, it is good practice to spend the night at one of the hotels closest to the airport. For instance, if you spend your night at Hampton Inn Portland Airport, which is located 1.1 miles from the airport, you will experience convenient access to the airport in the morning.
  • Flights from Portland to Puerto Rico mostly use Luis Muñoz Marín International Airport, also known as San Juan Airport (SJU), as the arrival airport. Landing at this airport puts you in one of the busiest cities in Puerto Rico, the city and municipality of Carolina. You will have a chance to feel the diverse culture and industriousness of the people of Puerto Rico.
  • Take flights from Portland to Puerto Rico as an opportunity to visit several other cities in addition to Carolina. Some of the cities near Carolina that you should include on the list of areas to visit are Canovanas, Trujillo Alto, and Puerto Rico.

Reviews of the top 4 airlines serving from Portland to Puerto Rico

 
Need help choosing which airline to fly with from Portland to Puerto Rico? 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 4295 reviews
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

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

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

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.

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.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

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.

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

The small flights with Valet Luggage has a poor service

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