$217 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 4/28. 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$741
Vieques
Vieques2 stops$1,735
Culebra
Culebra2 stops$1,056
Aguadilla
Aguadilla2 stops$741
Vieques
Vieques2 stops$1,735
Culebra
Culebra2 stops$1,056

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

sáb., may. 2 - sáb., may. 9
United Airlines Logo
8:04 am - 9:24 pm
PDX
-
SJU
10h 20m
1 stop
United Airlines Logo
7:40 am - 3:16 pm
SJU
-
PDX
10h 36m
1 stop
$496United Airlines
vie., may. 1 - sáb., may. 9
United Airlines Logo
11:59 pm - 3:42 pm
PDX
-
SJU
12h 43m
1 stop
United Airlines Logo
2:55 pm - 10:59 pm
SJU
-
PDX
11h 04m
1 stop
$512United Airlines
vie., may. 1 - sáb., may. 9
Southwest Logo
11:55 pm - 5:35 pm
PDX
-
SJU
14h 40m
2 stops
Southwest Logo
11:15 am - 10:05 pm
SJU
-
PDX
13h 50m
2 stops
$513Southwest
vie., may. 29 - dom., jun. 7
American Airlines Logo
6:15 am - 10:45 pm
PDX
-
SJU
13h 30m
2 stops
American Airlines Logo
6:20 am - 11:23 pm
SJU
-
PDX
20h 03m
1 stop
$530American Airlines
mié., jun. 3 - mié., jun. 10
American Airlines Logo
5:49 am - 10:45 pm
PDX
-
SJU
13h 56m
1 stop
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
PDX
19h 59m
1 stop
$535American Airlines
lun., may. 4 - sáb., may. 16
Multiple Airlines Logo
9:54 am - 1:15 pm
PDX
-
SJU
24h 21m
2 stops
Multiple Airlines Logo
4:10 pm - 5:06 pm
SJU
-
PDX
27h 56m
1 stop
$544Multiple Airlines
mar., jun. 9 - jue., jun. 18
American Airlines Logo
6:15 am - 10:45 pm
PDX
-
SJU
13h 30m
2 stops
American Airlines Logo
7:00 am - 11:59 pm
SJU
-
PDX
19h 59m
1 stop
$548American Airlines
mié., may. 6 - lun., may. 11
United Airlines Logo
11:55 pm - 2:44 pm
PDX
-
SJU
11h 49m
1 stop
United Airlines Logo
1:40 pm - 10:54 pm
SJU
-
PDX
12h 14m
1 stop
$549United Airlines
sáb., may. 2 - dom., may. 10
Southwest Logo
7:40 pm - 9:05 am
PDX
-
SJU
10h 25m
2 stops
Southwest Logo
5:35 am - 3:55 pm
SJU
-
PDX
13h 20m
2 stops
$551Southwest
mar., may. 19 - mar., may. 26
Multiple Airlines Logo
10:30 am - 8:05 am
PDX
-
CPX
18h 35m
2 stops
Multiple Airlines Logo
10:30 am - 1:10 pm
CPX
-
PDX
29h 40m
2 stops
$1,083Multiple 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 $489 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $745 and $688 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 17 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$211
Best time to beat the crowds with an average 12% 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 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 4330 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

My bags were misplaced!!! Im in a foreign country with no bags

The entertainment options on the seat back video boards were nice.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

The crew was very kind, but no in-flight entertainment monitors and a 2 hour and 30 minute delay was extremely frustrating.

Everything was delayed and the staff sent me to the wrong gate, causing me to miss one of my flights. I arrived at my destination 6 hours later than I was supposed to.

Got home at 3am after deboarding the plane. No compensation offered by American

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

It was really a terrific experience both going and returning on AA. Staff and crew were professional.

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

Information on your arrival and departure airports