$178 Find Cheap Flights from Portland to Puerto Rico - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Puerto Rico

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Vieques
Vieques2 stops$1,177
Vieques
Vieques2 stops$1,177
Booking Insights

Price, demand and travel trends for Portland to Puerto Rico flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Portland to Puerto Rico cheaper or more expensive than last year?

Fares from Portland to Puerto Rico are running about 5% higher than they were around this time last year, averaging $532 round-trip.

What are the cheapest fares from Portland to Puerto Rico right now?

The cheapest fare from Portland to Puerto Rico in the last week was $316 round-trip, to San Juan Luis Munoz Marin Intl (SJU).

What’s the cheapest month to fly from Portland to Puerto Rico?

October is the cheapest time of year to fly, with average fares of $362. Prices are highest in July, when average flight costs increase to around $696.

When is the best time to book flights from Portland to Puerto Rico?

Book your flights 22 weeks before your trip. KAYAK data collected over the past 12 months shows that booking in this window can save you around 43% compared to booking last-minute (within 2 weeks of departure).

Which airport in Puerto Rico is the cheapest to fly to from Portland?

All flights from Portland to Puerto Rico arrive at San Juan Luis Munoz Marin Intl (SJU). On average, round-trip fares are around $454.

What’s the cheapest day to fly from Portland to Puerto Rico?

Monday tends to be the cheapest day to fly from Portland to Puerto Rico, while Friday is the most expensive. Fares run about 33% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Portland to Puerto Rico?

Data from the past 12 months shows it's cheapest to fly to Puerto Rico during the afternoon with average prices of $400. The morning is the most expensive time to fly, with average prices of $520.

Key details for Portland to Puerto Rico flights

Low season

July

Cheapest flight

$178
Beat the crowds with an average 82% drop in travelers.
The most popular month to fly with an average 98% increase in travelers.
One-way flight from Portland to San Juan Luis Munoz Marin Intl Airport

Your Portland to Puerto Rico flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Portland to Puerto Rico?

    Yes. Fares from Portland to Puerto Rico are low right now. As a rule of thumb, a round-trip under $354 (cheaper than most fares this year) is a good deal, so if you spot one at or below that, it's a good time to book.

  • How much should I budget for a flight from Portland to Puerto Rico?

    Over the past 12 months, round-trip fares from Portland to Puerto Rico have ranged from $354 to $678.

  • What airlines fly nonstop from Portland to Puerto Rico?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Portland to Puerto Rico. One-stop options include:

    • Southwest
    • United Airlines
    • JetBlue

  • Which cabin classes are available on flights from Portland to Puerto Rico?

    On flights from Portland to Puerto Rico you can book Economy Class or First Class.

  • What are some popular landmarks in Puerto Rico?

    KAYAK travelers' favorite landmarks in Puerto Rico include:

    • Viejo San Juan
    • Puerto Rico Convention Center
    • Condado Beach
    • Ocean Park

Your guide to booking Portland to Puerto Rico flights

Get tips on when to book, when to fly and what to know before your trip.
  • If you can plan ahead, the sweet spot for booking your flight is 22 weeks before your trip. KAYAK data shows fares in this window are around 43% lower than last-minute bookings (made within 2 weeks of departure). Not ready to commit? Set a Price Alert and we'll let you know when prices change.
  • If your travel dates are flexible, book your trip for October when flights are typically cheapest and avoid July when prices are at their highest.
  • Flying on Monday is usually the cheapest. Flights on Friday cost about 33% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in San Juan, which is the most popular destination in Puerto Rico. From there, it's easy to continue on to other popular destinations such as Carolina, Fajardo and Rio Grande.

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.
7.9
SouthwestOverall score based on 4219 reviews
7.4Entertainment
8.6Crew
8.1Boarding
7.0Food
8.0Comfort
Airline reviews

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

4.0 OkayPatrick, Oct 2026
Read more Southwest reviews

The service was fine, about the same as you get on most lower end airlines. I dont understand the perks of flying them much anymore for the cost.

the flight was significantly delayed. Not much was done by the airline to compensate passengers

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

Had to walk back and forth between concourses to figure out which gate I was supposed to be at. The app and the flight board in the airport had different gates listed. Was told numerous times to check bags only to get on the plane and find that there was plenty of room for bags. The flight was over an hour late which had me landing after the last train departed. WiFi was unusable

My experience was okay I changed my returning flight and I was charged extra money which I dont think should be the case, especially because I experienced small delays from my going flight. And many flights were either canceled or delayed after my original flight time. I believe some customers should have the ability to change flights due to certain situations

I've taken four flights with Southwest within the last three months and every single flight was delayed.

It was great and arrived home a little sooner than expected which is nice.

I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.

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.

it was great. the crew is exceptional. the flight was on time.

I enjoyed the whole flight and the crew was amazing i dont usually fly delta

Very nice the whole crew was amazing and very professional. I had an offer for a drink it was handled great and amazing crew and nice flight.

I just wish the boarding process/time to take off after boarding was quicker and more efficient. I also wish that the overhead luggage was managed better. almost every time i fly there is no space for carry ons and they are either checked or I end up having to store it several rows back from my seat. Delta should not offer carryons for all customers if there is not actually space for everyone

Boarding was delayed by an hour and then we proceeded to sit on the tarmac for another 30-40 minutes. No clear explanation was ever given and the delay caused me to miss my connecting flight home. Was forced to stay the night in the connecting city which impacted my following workday and cause personal issues at home as well.

The wait in the tunnel to enter the plane was too long. The counter personnel, specially ''Israel'' was really not welcoming considering Delta Standards. Other than this everything was good overall.

an he late. super rude gate agent, to every person. spoke down at people.

It was good. The leg room was not great in Row 1.

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

When we checked in my friend and I were sitting seperate. By the time we got to boarding, they automatically switched our seats. I really liked that.

I trust Delta. I travel comfortable. The snacks could improve or could go to something as a little sandwich.

Worst boarding experience, flight extremely delayed causing super tight connect and deplaning was a disaster as ppl were pushing and shoving to get off. Then after flying over 8 hours had to get off a job to next flight. Limited beverage service in Business class (water or white wine) no food. The plane was very cold (temperature) so uncomfortable

Stored my cloth purse under seat in front off me as instructed. When I retrieved it, half of it was soaked, along with everything inside it. I don’t really know how that could have been prevented because the area did not look wet, but I was not happy about it.

Seats needs to be wirer and food is very poor

Seats are uncomfortable and left me in pain in my tailbone area. I got about one hour of sleep.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

Both my flight where delayed Had 25min to make it to my transfer flight

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.

My flight was completely full. Making me very stressful with people walking around all the time. I believe airlines can do better for entertain people during the flight.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

The United website was easy to use and had all the information I needed. I needed to change my flight and it was accomplished easily on line. I was also easily able to upgrade and for a reasonable price. Boarding went smoothly and the flight was in time. The service was good in board but the crew did not seem happy at all. Limited availability of meals - not much choice for purchase and in business class they ran out of one of the meal choices by row 4. .

What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

JetBlue is always consistent and great, the food is limited in selection, but at least you can grab as much as you want on snacks and drinks at the Blue Locker.

Very well organized both boarding and deplaning. Very satisfied with the service I received.

Flight was on time arrived at the destination 10min early they kept in touch via email

at the time for boarding the lady just call Group A and no other goups and everybody from A to F go inside without the right turn,and when we get in theres no more spsce for carry on , the ones that get in at not correct group from the back occupy our space !!!!! a mess !!!!

The boarding and flight were ok, but there were several painful issues. The flight was 3:20 in the air and almost four hours door to door, but they only had snack packs on the plane. They really need to have food on longer flights or make it clear to everyone that they won’t have food. They also advertise free WiFi, but it did not work for 90% of this flight. Again, almost four hours door to door. If I had known I was flying spirit for JetBlue prices then I would have planned differently.

I think the food / snack service was very poor. tehy could have done better. Evrything else was great

No wifi, not even while close to the continental US or Puerto Rico, no entertainment whatsoever (TVs not working). Totally disappointing.

Wifi screens were great. Both flights were delayed, spending all day flying home and then getting home at 3am ruins the next day also.

To many flight at the same hour...no respect to handicap....

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

Delayed delayed. Poor professionalism. Our seats changed and we pay for them

The plane was broken so we had to change planes.

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

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

Airlines must do something with overweight people... Maybe reserve a business class seat for them, or you could pay the consequences if someone overweight seat side by side to you in economy.

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.

More options for your flight from Portland to Puerto Rico

Complete your trip to Puerto Rico with a hotel stay or car rental