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Find cheap flights from Caribbean to Portland from $146

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 5/8. 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
0 bags
Sat 5/25
Sat 6/1

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In the last 7 days travelers have searched 45,119,101 times on KAYAK, and here is why:

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Good to know

Low season

February

High season

July

Cheapest flight

$146
Best time to beat the crowds but there is an average 14% increase in price.
Most popular time to fly with an average 18% 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.

See more FAQs

Prefer to fly non-stop from Caribbean to Portland?

Find which airlines fly direct from Caribbean to Portland, which days they fly and book direct flights.

Nonstop departures

Caribbean to Portland

Monday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Tuesday

ANA, Aer Lingus, Aeromexico, +50 more

ANA, Aer Lingus, +51 more

Wednesday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Thursday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Friday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Saturday

ANA, Aer Lingus, Aeromexico, +50 more

ANA, Aer Lingus, +51 more

Sunday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

See more direct flights

Nonstop returns

Portland to Caribbean

Monday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Tuesday

ANA, Aer Lingus, Aeromexico, +50 more

ANA, Aer Lingus, +51 more

Wednesday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Thursday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Friday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

Saturday

ANA, Aer Lingus, Aeromexico, +50 more

ANA, Aer Lingus, +51 more

Sunday

ANA, Aer Lingus, Aeromexico, +51 more

ANA, Aer Lingus, +52 more

See more direct flights
See more direct flights

Top 5 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
DeltaOverall score based on 10975 reviews
7.9comfort
8.6crew
8.2boarding
7.4food
8.0entertainment
Airline reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

6.0 GoodDan, Apr 2024LGA - DEN
Read more about Delta reviews

I'm a larger, athletic guy (6'2", 260lbs powerlifter) and I found the seats incredibly uncomfortable with minimal leg room, especially in a window seat. Now, I full understand that being smaller may change my view but even if I was 80lbs less, my legs would be the same size and I was sandwiched between my seat and the seat in front of me.

Horrible. This was not first class. This was a connecting flight whi h was late. My original flight never came. I hated the fact that delta gave me a connecting flight from New York to Orlando Florida. No meals and the television screens were not working. There wasn't even any power to charge your phones. This is NOT FIRST CLASS DELTA!!! Do better next time!

This flight was ridiculous. I had to have a connecting flight from New York to orlando Florida??? The flight left late and because it was a short flight there was no first class amenities. I had one alcohol drink. The flight crew was fine, but it sure did not feel like first class. Delta to me dropped the ball by giving me a connecting flight. By the time we got to Raleigh we would have missed the next flight. Lucky for me the flight never came so now I was stuck waiting for a later flight that came in late also.

Our flight was delayed in Atlanta. The staff could have gave us an explanation for the delay and how long it would be.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

Flight was delayed an no one make an announcement about it., they only have Coca Cola and nothing else., the food that was served was cold… very bad experience and service

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive. I also upgraded to comfort + , I didn’t feel it was worth it. There was no benefit

On my way home I had a layover. The flight from ATL to CLT was amended 5x while I was waiting. I could have driven home sooner. Overall from Dallas, Tx to Charlotte, NC I started my trip at 4:30pm, I didn’t get home until past midnight. I know things happen, but 5x to make me run back and forth in an airport from different terminals is excessive.

They did a fine job. Can't wait to use Delta in the future.

There was a loud squeaky sound the whole time we were flying.

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Flew business class. Everything was excellent. No issues at all. Not very many “good” movies to choose from. But lots of mediocre ones

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

The best experience that I have had traveling with JetBlue!

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

Crew was just ok. Flight was packed. On a 3/4 hour flight I would hope they would come around more than once to see if you needed anything further. Not very attentive.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

Nothing. Jet Blue is a great choice for me And I’m going to miss flying with them Since I travel to Lima Peru very often 😞😞😞

Due to one crew member not showing up to work, our flight was significantly delayed causing us to miss our connecting flight in Houston to Mississippi causing us to be delayed by more than 6 hours and missing our event all together. Very disappointing. All because ONE crew member called in sick. United did grant us a $15 meal voucher, which was a small but appreciated concession that I wasn’t able to use because I ordered my lunch and paid for it before applying the concession, and the staff said it was too late to use it. Ugh! We also had a TWO delay coming back from Mississippi, but that was on American Airlines and it was due to weather, so not their fault. Anyway, not at all impressed with United’s handling of our flight and the HUGE disappointment of missing our important family event for our 90 year old mother. All that money and all that stress and emotions for nothing. Having to wait the hour to bring an employee from LAX seemed like something that should not have happened. Why don’t you have a local back-up? Santa Ana is not a little airport in a rural area.

Terrible. 2 hour delay. Sat on the tarmac. Missed my connecting flight. Had to ARGUE with Customer service to get a hotel and food. Terrible experience with my loyal carrier

Our seat tv didn’t work All the rest was perfect

Flight delayed from Cape Town to Washington then got diverted to miami and in miami we had to fend for ourselves , im still trying to get to Shreveport now

I liked the exit row seat. Hated the distance between gates in Houston.

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

I just wrote a text which was supposed to be for the flight from Denver to spokane not Frankfurt to Denver.

On time every leg of the journey and exceptional staff at counter, gate, and on board. I haven’t travelled in US for a long time and was genuinely surprised how pleasant this was.

Meals were adequate but could be better. Lots of movies, podcasts, tv shows. We really enjoyed using our personal headsets highly recommended. 15 hrs flight great to travel at night.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

A disaster, I lost my connection due to overcrowding at the Miami airport, having a 3-hour layover and the airline did nothing to reboard me on time and I had to sleep on the floor for 18 hours.

The food has never improved. It will never improve. But when I'm boarding a flight in priority boarding and I've spent 10 hours inside the security area of the airport and I get "randomly" selected for additional screening as I board the plane when the flight has already been delayed, and I work as a military contractor that has been issued visas direct from JMOD, I find it ridiculous. I would never recommend anyone to use AA on international flights. JAL is a better airline with older planes. The flight attendants on international hauls on American also have a chip on their shoulder and really dont deliver the same level of service code share partners do.

The flight was 90 minutes long and the stewardesses were extremely slow. I was in row 16 and they did not serve us drinks until we were descending for landing in a 90 minute flight. Unacceptably slow and at least 10 rows (20 to 31) did not receive any drinks or snacks for the entire duration of the flight because of the slowness of the stewardesses. There is no rationale to delay beverage service to brew coffee for a flight at six p m.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

The Flight attendant had an attitude and didn't allow anyone any time to prepare for landing despite being absent throughout the entire trip

Flight boarded without pilots. Sat on plane for 3 hrs. after over an hour late boarding. Plane never took off. Had to deplane near midnight. Line for rebooking was 3 hours + long. I had to leave.

The flight was great but board was a nightmare. The gate was changed 4 times during the layover period

The experience was great and much better than the flight going out. of course I was in first class but the service was excellent

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

I do not like the customer service, I had an emergency and needed to cancel a pet reservation right after I had booked it and they would not do anything but issue a credit. I haven't flown in years as I have 7 kids and don't have spare time. I want my $125 back on my card please

Spirit airline tries to screw you at every opportunity. Spirit wanted 65$ for an extra pound in the suitcase Made me open the suitcase at the counter to remove 1 pound. Staff very cold and rude Will never fly spirit again and will recommend same to family and friends

Delayed..4 times...completely disorganized boarding. After 5 hours they scrambled to move ppl off plane bc they overbooked. Then they didn't have a cabin crew. WiFi on plane didn't work. Zero amenities. Once we boarded we sat on tarmac for an hour. Explore all alternate options including purchasing a pair of hiking boots and walking to your destination instead of flying spirit.

what I like about Spirit is that the pilot and crew are good communicators. The plane itself - well, its a budget airline and you get what is expected, But I generally just feel safer, somehow, when I know more about what is going on - and Spirit has always done a good job of telling me what is going on: why the delay, why the turbulence, why this and that... and that means a lot to me.

I paid just under 200 for flight and luggage, then paid 200 to change the flight, then paid 100 for a carry on. Then the cancelled the flight. Of the 500 I spent they refunded 250. I bought a delta flight for 270 never flew with spirit, but spirit kept 250, not even refunding the 100 for the carry on though they cancelled the flight (for weather on a day with only a slight rain ).

Book cheap flights from Caribbean to Portland

Recent round-trip flight deals

5/17Fri
2 stopsFrontier
23h 57mMBJ-PDX
5/31Fri
2 stopsFrontier
21h 26mPDX-MBJ
$316
6/1Sat
1 stopSpirit Airlines
19h 20mSJU-PDX
6/12Wed
1 stopSpirit Airlines
10h 08mPDX-SJU
$322
6/8Sat
1 stop
24h 07mSJU-PDX
6/15Sat
1 stop
9h 54mPDX-SJU
$360
6/19Wed
1 stop
19h 44mSJU-PDX
7/4Thu
1 stop
9h 47mPDX-SJU
$372
9/24Tue
2 stopsUnited Airlines
16h 54mSJU-PDX
10/4Fri
3 stopsUnited Airlines
15h 49mPDX-SJU
$427
9/25Wed
2 stopsDelta
14h 02mSJU-PDX
10/4Fri
1 stopDelta
11h 44mPDX-SJU
$428
5/16Thu
2 stopsUnited Airlines
32h 20mMBJ-PDX
5/30Thu
1 stopUnited Airlines
11h 00mPDX-MBJ
$451
5/16Thu
1 stopAmerican Airlines
15h 19mMBJ-PDX
5/30Thu
1 stopAmerican Airlines
12h 13mPDX-MBJ
$459
5/16Thu
2 stopsAmerican Airlines
21h 33mMBJ-PDX
5/30Thu
1 stopAmerican Airlines
12h 13mPDX-MBJ
$462
5/16Thu
2 stopsDelta
22h 26mMBJ-PDX
5/29Wed
2 stopsDelta
12h 54mPDX-MBJ
$463

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Recent one-way flight deals

5/8Wed
3 stopsSpirit Airlines
28h 23mSJU-PDX
$146
5/7Tue
2 stopsSpirit Airlines
33h 26mPUJ-PDX
$147
6/7Fri
1 stopUnited Airlines
11h 16mSJU-PDX
$191
5/7Tue
1 stopAmerican Airlines
15h 07mSJU-PDX
$234
8/23Fri
2 stopsAmerican Airlines
22h 22mSJU-PDX
$235
8/23Fri
1 stopDelta
13h 41mSJU-PDX
$251
7/4Thu
2 stopsUnited Airlines
28h 18mPLS-PDX
$273
8/19Mon
1 stopDelta
13h 41mSJU-PDX
$274
7/24Wed
1 stopJetBlue
12h 50mSJU-PDX
$324
6/25Tue
1 stopJetBlue
14h 08mSJU-PDX
$373

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Last minute flights from Caribbean to Portland

Last minute flight, train and bus deals

4/26Fri
multi-stopFrontier
15h 12mPUJ-PDX
4/28Sun
multi-stopFrontier
12h 25mPDX-PUJ
$607
4/28Sun
multi-stopAmerican Airlines
20h 14mSJU-PDX
4/30Tue
multi-stopAmerican Airlines
18h 35mPDX-SJU
$745
4/28Sun
multi-stopAmerican Airlines
20h 14mSJU-PDX
4/30Tue
multi-stopAmerican Airlines
13h 37mPDX-SJU
$746
4/26Fri
multi-stopJetBlue
12h 07mPUJ-PDX
4/29Mon
multi-stopJetBlue
10h 22mPDX-PUJ
$867
4/27Sat
multi-stopUnited Airlines
14h 03mSJU-PDX
4/30Tue
multi-stopUnited Airlines
10h 09mPDX-SJU
$889
4/26Fri
multi-stopDelta
18h 20mSDQ-PDX
4/28Sun
multi-stopDelta
13h 59mPDX-SDQ
$891
4/26Fri
multi-stopDelta
21h 24mSDQ-PDX
4/28Sun
multi-stopDelta
16h 59mPDX-SDQ
$896
4/27Sat
multi-stopUnited Airlines
13h 33mSJU-PDX
4/30Tue
multi-stopUnited Airlines
11h 52mPDX-SJU
$1,028
4/27Sat
multi-stopSpirit Airlines
17h 31mSJU-PDX
4/30Tue
multi-stopSpirit Airlines
20h 29mPDX-SJU
$1,105
4/27Sat
multi-stopSpirit Airlines
17h 31mSJU-PDX
4/30Tue
multi-stopSpirit Airlines
16h 27mPDX-SJU
$1,144

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Flights to Portland

Destination:

Portland (PDX)United States

Return flight deals:

Portland - Caribbean

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