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Find cheap flights from Portland to Caribbean from $137

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 Caribbean departing on 5/26. 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
Fri 5/31
Fri 6/7

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$394
Montego Bay
Montego Bay2 stops$331
Santo Domingo
Santo Domingo1 stop$336
Oranjestad
Oranjestad2 stops$439
Nassau
Nassau1 stop$346
Simpson Bay
Simpson Bay1 stop$444
Providenciales
Providenciales2 stops$446
George Town
George Town1 stop$537

Good to know

Low season

July

High season

April

Cheapest flight

$137
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly with an average 17% increase in price.
Flight from Portland to San Juan

FAQs - booking Caribbean flights

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

    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 Caribbean.

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

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

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

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

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

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 22% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Portland to Caribbean

 
Need help choosing which airline to fly with from Portland to Caribbean? 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 10895 reviews
8.0Entertainment
8.2Boarding
8.6Crew
7.4Food
7.9Comfort
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

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

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.

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.

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 !!!!

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.

I had back trouble prior to my flight and everyone was great about helping me.

Jetblue needs to improve on Onboarding as it seems to always be behind on departing. It never leaves on time. I would recommend to have an earlier Onboarding in order to leave on time and respect your customers time as well.

40 minute delay before take off after boarding flight. Bright lights throughout night flight due Issues with light panels. In flight Entertainment nonfunctional

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Food was terrible Not many options Stewards dont care Delay

Water service would be great. The way they board is terrible. Slow passengers first😂😂 They need to smart up a bit

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

The ride was good but no food ot entertainment hence, it was just over an hour flight.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

Not being able to purchase my check in baggage online was a negative.

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

WiFi connected but only let you go to the AA website, not even text messaging worked.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Book cheap flights from Portland to Caribbean

Recent round-trip flight deals

6/24Mon
1 stopJetBlue
7h 03mPWM-SJU
7/5Fri
1 stopJetBlue
6h 29mSJU-PWM
$270
10/26Sat
1 stopDelta
8h 24mPWM-SJU
11/6Wed
1 stopDelta
7h 59mSJU-PWM
$274
5/12Sun
1 stopFrontier
24h 58mPWM-SJU
5/18Sat
1 stopFrontier
28h 02mSJU-PWM
$305
6/8Sat
1 stopAmerican Airlines
7h 07mPWM-SJU
6/14Fri
2 stopsAmerican Airlines
29h 05mSJU-PWM
$322
10/18Fri
2 stopsAmerican Airlines
18h 27mPWM-MBJ
10/25Fri
2 stopsAmerican Airlines
19h 20mMBJ-PWM
$331
6/13Thu
1 stopFrontier
14h 24mPWM-SJU
6/17Mon
1 stopFrontier
10h 54mSJU-PWM
$354
5/21Tue
1 stopUnited Airlines
6h 27mPWM-MBJ
6/1Sat
1 stopUnited Airlines
6h 46mMBJ-PWM
$427
5/25Sat
2 stopsUnited Airlines
18h 55mPWM-MBJ
5/31Fri
1 stopUnited Airlines
7h 14mMBJ-PWM
$432
5/27Mon
3 stops
23h 36mPWM-NAS
5/31Fri
2 stops
11h 44mNAS-PWM
$587
5/17Fri
3 stops
23h 51mPWM-SJU
5/19Sun
2 stops
13h 58mSJU-PWM
$635

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Recent one-way flight deals

5/26Sun
1 stopDelta
8h 59mPWM-SJU
$137
5/10Fri
1 stopFrontier
10h 54mPWM-SJU
$139
5/25Sat
1 stopJetBlue
6h 46mPWM-SJU
$151
5/21Tue
1 stopUnited Airlines
6h 27mPWM-MBJ
$155
5/21Tue
2 stopsAmerican Airlines
28h 32mPWM-MBJ
$182
5/22Wed
1 stopJetBlue
6h 51mPWM-SJU
$185
5/25Sat
2 stopsUnited Airlines
18h 55mPWM-MBJ
$187
5/10Fri
3 stops
33h 34mPWM-SJU
$202
5/10Fri
2 stops
24h 42mPWM-SJU
$211
6/27Thu
2 stopsAmerican Airlines
19h 25mPWM-PUJ
$219

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Last minute flights from Portland to Caribbean

Last minute flight, train and bus deals

5/3Fri
multi-stopFrontier
13h 23mPWM-SJU
5/13Mon
multi-stopFrontier
9h 02mSJU-PWM
$408
5/3Fri
multi-stopJetBlue
6h 51mPWM-SJU
5/14Tue
multi-stopJetBlue
9h 04mSJU-PWM
$536
5/5Sun
multi-stop
27h 29mPWM-MBJ
5/12Sun
multi-stop
20h 24mMBJ-PWM
$599
5/3Fri
multi-stop
29h 35mPWM-NAS
5/5Sun
multi-stop
22h 09mNAS-PWM
$659
5/4Sat
multi-stopAmerican Airlines
9h 05mPWM-MBJ
5/11Sat
multi-stopAmerican Airlines
20h 37mMBJ-PWM
$669
5/2Thu
multi-stopDelta
7h 07mPWM-STT
5/9Thu
multi-stopDelta
7h 37mSTT-PWM
$708
5/2Thu
multi-stopAmerican Airlines
18h 06mPWM-STT
5/9Thu
multi-stopAmerican Airlines
18h 53mSTT-PWM
$723
5/3Fri
multi-stopAmerican Airlines
14h 46mPWM-SJU
5/14Tue
multi-stopAmerican Airlines
17h 52mSJU-PWM
$778
5/5Sun
multi-stopUnited Airlines
6h 27mPWM-MBJ
5/12Sun
multi-stopUnited Airlines
21h 47mMBJ-PWM
$786
5/3Fri
multi-stopUnited Airlines
7h 40mPWM-SJU
5/13Mon
multi-stopUnited Airlines
9h 39mSJU-PWM
$802

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