$222 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 10/12. 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$744
Culebra
Culebra2 stops$1,558
Aguadilla
Aguadilla2 stops$744
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

Mon, Aug 24 - Fri, Aug 28
Southwest Logo
11:30 pm - 1:35 pm
PDX
-
SJU
11h 05m
2 stops
Southwest Logo
5:00 am - 3:00 pm
SJU
-
PDX
13h 00m
2 stops
$466Southwest
Sat, Aug 22 - Sun, Aug 30
Southwest Logo
10:45 pm - 1:00 pm
PDX
-
SJU
11h 15m
1 stop
Southwest Logo
5:30 am - 12:45 pm
SJU
-
PDX
10h 15m
1 stop
$498Southwest
Thu, Sep 3 - Thu, Sep 10
Southwest Logo
10:45 pm - 2:30 pm
PDX
-
SJU
12h 45m
1 stop
Southwest Logo
5:30 am - 3:00 pm
SJU
-
PDX
12h 30m
1 stop
$516Southwest
Fri, May 29 - Sun, Jun 7
American Airlines Logo
6:15 am - 10:45 pm
PDX
-
SJU
13h 30m
2 stops
American Airlines Logo
6:21 am - 11:23 pm
SJU
-
PDX
20h 02m
1 stop
$530American Airlines
Mon, Sep 14 - Tue, Sep 22
Delta Logo
7:00 am - 11:44 pm
PDX
-
SJU
13h 44m
1 stop
Delta Logo
7:00 am - 11:53 pm
SJU
-
PDX
19h 53m
2 stops
$531Delta
Tue, Jul 28 - Mon, Aug 3
American Airlines Logo
10:57 pm - 2:50 pm
PDX
-
SJU
12h 53m
2 stops
American Airlines Logo
2:25 pm - 11:30 pm
SJU
-
PDX
12h 05m
1 stop
$532American Airlines
Tue, Jul 28 - Mon, Aug 3
American Airlines Logo
10:30 pm - 1:33 pm
PDX
-
SJU
12h 03m
1 stop
American Airlines Logo
7:00 am - 11:30 pm
SJU
-
PDX
19h 30m
1 stop
$533American Airlines
Tue, Jul 28 - Mon, Aug 3
Multiple Airlines Logo
5:16 pm - 12:41 am
PDX
-
SJU
28h 25m
3 stops
Multiple Airlines Logo
9:00 am - 11:59 pm
SJU
-
PDX
41h 59m
3 stops
$549Multiple Airlines
Fri, Aug 21 - Fri, Aug 28
United Airlines Logo
5:00 am - 11:09 pm
PDX
-
BQN
15h 09m
2 stops
United Airlines Logo
12:15 am - 9:54 am
BQN
-
PDX
12h 39m
1 stop
$744United Airlines
Fri, Aug 21 - Fri, Aug 28
United Airlines Logo
5:00 am - 11:09 pm
PDX
-
BQN
15h 09m
2 stops
United Airlines Logo
12:15 am - 11:35 am
BQN
-
PDX
14h 20m
2 stops
$767United 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 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$222
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.
7.9
SouthwestOverall score based on 4305 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
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!

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.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

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.

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.

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 Puerto Rico

Information on your arrival and departure airports