$138 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 4/29. 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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Flight Deals

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, Apr 27 - Tue, May 5
Southwest Logo
3:00 pm - 10:35 am
PDX
-
SJU
16h 35m
2 stops
Southwest Logo
5:05 am - 9:00 pm
SJU
-
PDX
18h 55m
2 stops
$386Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
9:45 am - 11:40 pm
PDX
-
SJU
10h 55m
2 stops
Southwest Logo
5:05 am - 9:00 pm
SJU
-
PDX
18h 55m
2 stops
$406Southwest
Mon, May 25 - Thu, May 28
JetBlue Logo
11:40 pm - 11:00 pm
PDX
-
SJU
20h 20m
1 stop
JetBlue Logo
1:45 pm - 10:25 pm
SJU
-
PDX
11h 40m
1 stop
$411JetBlue
Wed, Apr 22 - Thu, Apr 23
Southwest Logo
5:30 am - 9:05 pm
PDX
-
SJU
12h 35m
2 stops
Southwest Logo
2:00 pm - 12:10 am
SJU
-
PDX
13h 10m
2 stops
$436Southwest
Tue, May 12 - Tue, May 19
Southwest Logo
7:25 pm - 10:35 am
PDX
-
SJU
12h 10m
2 stops
Southwest Logo
11:25 am - 11:10 pm
SJU
-
PDX
14h 45m
2 stops
$437Southwest
Wed, Apr 1 - Wed, Apr 15
Multiple Airlines Logo
9:30 pm - 3:17 pm
PDX
-
SJU
14h 47m
1 stop
Multiple Airlines Logo
3:19 pm - 8:59 am
SJU
-
PDX
44h 40m
3 stops
$441Multiple Airlines
Mon, Mar 9 - Wed, Mar 11
American Airlines Logo
10:53 pm - 8:50 pm
PDX
-
SJU
18h 57m
1 stop
American Airlines Logo
6:33 am - 5:08 pm
SJU
-
PDX
13h 35m
2 stops
$445American Airlines
Wed, Apr 1 - Wed, Apr 15
Multiple Airlines Logo
9:30 pm - 3:17 pm
PDX
-
SJU
14h 47m
1 stop
Multiple Airlines Logo
10:53 am - 11:44 pm
SJU
-
PDX
15h 51m
2 stops
$446Multiple Airlines
Tue, Jul 21 - Wed, Jul 29
United Airlines Logo
10:00 am - 11:09 pm
PDX
-
BQN
10h 09m
1 stop
United Airlines Logo
12:15 am - 9:21 am
BQN
-
PDX
12h 06m
1 stop
$521United Airlines
Tue, Jul 21 - Wed, Jul 29
United Airlines Logo
7:00 am - 11:09 pm
PDX
-
BQN
13h 09m
2 stops
United Airlines Logo
12:15 am - 9:21 am
BQN
-
PDX
12h 06m
1 stop
$588United 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 October, when tickets cost $468 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $759 and $683 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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonJuly
Cheapest flight$138
Best time to beat the crowds with an average 6% 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 5 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 4293 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

First flight out and was 85 minutes delayed. Notification came out way too late

Delta flights recently are always delayed AND at jfk tney get the gates further away (need To walk 20’ to get to them/all the way at the end of the terminal). Not sure whats happening but price doesnt match experience!

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

As great a red-eye flight as red-eye flights can be.

Once boarding started it was pretty quick. Food was inedible; cold and salty..

Entertainment kept turning itself off. Gave up on watching a movie.

Both the WIFI and entertainment did not work for 2.5h

The crew made our experience extremely bad. They were rude and didn’t have anything for kids.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

No Snacks or Entertainment. The flight was short, snacks should still be given.

We lost a day of our vacation because AA did not get the plane to the gate on time. Even though the gate attendant was very clear that it was not weather related, AA would do nothing because there was some snow that day. They basically said the gate attendant was wrong even though she was on the front line of the situation and they were not.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

Overall it was a good flight. Because we traveled on a Saturday we were upgraded to FC since my wife and I are both Executive Platinum. The only areas for improvement we noted are better snack assortment and perhaps a little nicer plane as American is flying some older planes now. Everything else on this flight was excellent, which is frankly not the norm for American since we have had multiple issues on prior AA flights.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

I paid for the seats in row 3 to embark and disembark quicker but the passengers in the 2 rows in front of me take all the overhead bin space so I am forced to put my luggage 5 rows back. I even opened one up right above my seat which had room but as I was going to fit my carry on a flight atendant said it "was reserved", Just giving my money to a regular airline next time.

Terrible Flight was cancelled last minute with no other flights available

I was not informed via text about flight delay and gate change. There should have been a notice by the original gate letting us know that there was a change. A half hour before original flight time we realized there was no one there and were told that the gate was changed so we ran across the airport (I was traveling with my aunt who is in her upper 60s) to try to make the flight and then saw that the flight was actually delayed an hour . If you can do something for us to makeup for this we would appreciate it. Thank you

Terrible. Spirit cancelled the flight with 3 hours notice and were absolutely no help getting another flight. Had to make my own reservation on another airline and arrived in Dallas 12 hours later.

The flight itself was great except for an air traffic controller delay. We left 30 min late but they made up most of the time in flight. The booking was frustrating, as we chose a certain flight and it was changed four times. We got to Orlando several hours later than the original flight we chose.

Crew was very nice. Take off and landing were great. Economy seats are not comfortable. Extra cost for snacks.

Less than acceptable. Family members had flights cancelled with no reason. Multiple hour delay, gate changes, poor communication, less than satisfactory. I will never fly with spirit again, which is a shame because it’s a budget friendly option but quite frankly with all of the hassle and hoops that come with flying spirit. Completely unacceptable.

Everything was terrible. Flight was delayed several hours, crew was abrasive. Stuck on runway for over a hour. There was an argument between passengers that nearly turned into a fight while waiting to exit plane, crew did nothing. Took nearly 3 hours to retrieve luggage at baggage claim. Lost an entire day of vacation. Will never fly spirit again under any circumstance

There absolutely needs to be WiFi on flights. Not sure why this new aircraft did not have the capability, but it made for a very frustrating flight. I honestly would have paid twice as much for another airline to have WiFi as an option, especially as a mom with kids who have disabilities.

More comfortable seats, free snacks and soft drinks, some sort of entertainment or WiFi.

Everything you need to know for your flight from Portland to Puerto Rico

Information on your arrival and departure airports