$140 Find Cheap Flights from Caribbean to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 4/24. 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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Everything you should know

Cheapest round-trip
$440
Overall average: $523
American Airlines
Fri 4/3Mon 4/6
SJU - PDX • 1 stop
Cheapest one-way
$140
Typical prices: $213-$398
Frontier
Fri 4/24
SJU - PDX • 2 stops
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Portland

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

Fri, Apr 3 - Mon, Apr 6
American Airlines Logo
6:00 am - 12:22 am
SJU
-
PDX
21h 22m
1 stop
American Airlines Logo
11:30 pm - 3:08 pm
PDX
-
SJU
12h 38m
2 stops
$440American Airlines
Tue, Feb 24 - Sat, Feb 28
American Airlines Logo
7:00 am - 11:50 pm
SJU
-
PDX
20h 50m
1 stop
American Airlines Logo
5:43 pm - 10:00 am
PDX
-
SJU
12h 17m
2 stops
$445American Airlines
Thu, Jun 25 - Tue, Jun 30
JetBlue Logo
12:30 pm - 10:25 pm
SJU
-
PDX
12h 55m
1 stop
JetBlue Logo
11:40 pm - 4:05 pm
PDX
-
SJU
13h 25m
1 stop
$471JetBlue
Fri, Feb 27 - Fri, Mar 6
United Airlines Logo
2:25 pm - 11:14 pm
SJU
-
PDX
12h 49m
1 stop
United Airlines Logo
11:59 pm - 3:40 pm
PDX
-
SJU
11h 41m
1 stop
$513United Airlines
Thu, Jun 25 - Tue, Jun 30
JetBlue Logo
12:30 pm - 10:25 pm
SJU
-
PDX
12h 55m
1 stop
JetBlue Logo
11:40 pm - 4:05 pm
PDX
-
SJU
13h 25m
1 stop
$521JetBlue
Thu, Apr 2 - Sat, Apr 11
United Airlines Logo
1:40 pm - 10:54 pm
SJU
-
PDX
12h 14m
1 stop
United Airlines Logo
5:00 am - 8:38 pm
PDX
-
SJU
12h 38m
2 stops
$530United Airlines
Tue, Jun 9 - Fri, Jun 19
Multiple Airlines Logo
9:00 am - 10:25 pm
SJU
-
PDX
16h 25m
2 stops
Multiple Airlines Logo
11:59 pm - 3:18 pm
PDX
-
SJU
12h 19m
1 stop
$547Multiple Airlines
Tue, Apr 28 - Fri, May 1
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
7:00 am - 12:17 am
PDX
-
SDQ
14h 17m
1 stop
$603Delta
Tue, Apr 28 - Fri, May 1
Delta Logo
6:05 am - 10:16 pm
SDQ
-
PDX
19h 11m
1 stop
Delta Logo
7:00 am - 12:17 am
PDX
-
SDQ
14h 17m
1 stop
$661Delta
Fri, Apr 10 - Sun, Apr 19
Multiple Airlines Logo
7:00 am - 8:35 pm
GCM
-
PDX
15h 35m
1 stop
Multiple Airlines Logo
7:00 am - 11:35 am
PDX
-
GCM
26h 35m
1 stop
$722Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$140
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean to Portland

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

    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 Caribbean to Portland.

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

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

    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 to Portland with an airline and back to Caribbean with another airline.

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

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

Reviews of the top 4 airlines serving from Caribbean to Portland

 
Need help choosing which airline to fly with from Caribbean to Portland? 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 4267 reviews
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Very convenient considering that is a non-stop flight, but the Aeromexico still has old model planes, so the entertainment was very poor and the space for carry-on luggage was very limited.

Flight taking off must have been behind, because there was no pre-departure drink for first class like normal. Also, person in front of mine’s seat got stuck in the as far back as it normally goes position for the whole flight even during landing, flight attendant unable to fix it. Gate was not empty when we arrived, but that is MSP’s fault since was overdue for push back, not Delta’s, so had to sit on tarmac for a while and international flight so then still had to go through customs. Flight crew was excellent throughout though!

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

This Japanese airline provides great service and very helpful in assisting their passengers.

Good crew. Boarding delays. Almost two hours wait for the bags in DC.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Flight arrived 30 min early and bag was waiting at the baggage pickup. United Club HNL was one of the nicest in the system

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

Crew was clearly not loving their jobs at any point of the entire trip. Flight back from Mexico, I asked if they had food for sale for the 2.5+hr flight and they did not have any. The business class trip to Mexico also had noted that the catering company forgot to load food. The last leg of trip back had a similarly unhappy crew, a broken toilet, and my seat was broken (reclining would not lock which made landing a crossfit like event). This was a bad week for AA.

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

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