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Find cheap flights from Portland to Caribbean from $141

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 8/16. 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
Sun 6/30
Sun 7/7

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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$363
Montego Bay
Montego Bay2 stops$412
Santo Domingo
Santo Domingo1 stop$432
Oranjestad
Oranjestad2 stops$373
Nassau
Nassau1 stop$492
Kingston
Kingston2 stops$630
Providenciales
Providenciales1 stop$443
George Town
George Town2 stops$520

Good to know

Low season

July

High season

April

Cheapest flight

$141
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly with an average 21% increase in price.
Flight from Portland to Montego Bay

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 6% cheaper 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 10438 reviews
7.9Comfort
8.2Boarding
7.4Food
8.0Entertainment
8.6Crew
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Well....let's start from the point that I had to stay in airport for 12 hours instead of 2 that was scheduled. Poor company and even worst customer service. Never again....

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

We liked the fully reclinable seats. Had center seats, so it was difficult to talk to spouse. Crew was great

Aisle chair was good and liked the foot bar preventing you from putting your foot in the isle, The breakfast on this international flight to Zurich was horrible (Europeans, specially, used to good food) may make this a dealbreaker for booking with United Airlines again. I agreed with my Spanish fellow passenger.

Dinner was okay but the breakfast was not eatable on the flight San Francisco to Zurich.

There was no screens on board AND the WiFi didn’t work. My seat was broken and couldn’t recline so I couldn’t even sleep. The flight attendants didn’t offer anything to make it more comfortable. It was such an old cramped plane, when the person in front of me reclined I couldn’t even open my tray table. All the United ads talk about guaranteeing everyone gets a screen!

The Wi-Fi was unavailable on this flight for some reason.

The flight was delayed almost 2 hours. Bad customer service etc. I will never fly Luthansa. Ever!!!

On time take off…US cabins look tired and need of refresh!

Fine. Though no food or entertainment so the survey needs to be updated with those options.

My husband and I pre-ordered our food, but they did not have my husband’s order, and my cheese plate was very average. I asked for a blanket and was told they don’t carry blankets on domestic routs. The flight was on time and smooth!

28 hour delay at Fort Worth/Dallas airport, part due to weather which was unavoidable, but various other reasons - no pilot, no fa, mechanical problem, plane too small, too big, crew out of flying time, seat configuration problems.... endless and hourly updates with a different excuse. Finally told us about 3.00 am, that the flight was delayed to hours later.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

Original flight delayed several times and finally canceled at 2:30 in the morning. Staff at the gate was not very helpful in resolving problems or communicating why there were delays. I spent 34 hours at the airport before I could leave, they couldn't book me on another early flight even after canceling my original flight. Next flight available after my original flight was canceled was 22 hours later. I will never fly American Airlines again.

very very tight seats unfriendly crew who do not seem to care about the comfort of their passengers and do not know how to smile poor ground staff support at LHR and PHX

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

So uncomfortable to sit in the tiny space on a long, international. Food was rough. Please, less white flour and processed food.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

It was delayed 9 hours for operational reasons, despite the plane arriving to the airport on time.

I am very disappointed with Frontier Airlines. They cancelled our flight because they couldn't find a crew member, and then didn't get us to our connecting flight. We had to cancel our whole vacation. We were promised flight and hotel vouchers, but they never sent them.

9hrs delay and didn’t provided anything until after flight landed $75 voucher for fiuture travel no meals or anything.

It was ridiculously hard to check in for the flight, and Frontier charged us a LOT of money to have a carry on suitcase, and then told everyone we could not carry on bags and had to check them through at the gate, and didn't refund the extra money we paid to have the suitcase as carry on.

I had a terrible experience with Frontier. I arrived before the 60 minute cut off and was told that Frontier has a two hour window for bags. I was then told the next available flight wasn’t until the end of the day (I had booked a 6am flight). I took a look around and saw other people being told that they could not board their flights or that they had to pay additional fees. I opted to rebook on American Airlines. There’s absolutely no straightforward way to contact Frontier, so this ticket was a complete waste of money. Oh - and the kicker is that the lady lied about the two hour cut off.

Frontier won’t help you at the airport without paying $25. Carry on was $75. Then you get on the plain and every beverage or snack is also a charge. Seats are hard and real packed in. I would never fly them again.

Worst experience I have seen. The flight was cancelled without any reason.

My experience with frontier staff at the Denver airport was absolutely horrible. The manager on duty was even worst if was the worst experience I have ever had, I have never been treated so poorly as a customer in my life! The staff was extremely rude, eye rolls and attitude and then refusal to help me at all. I wish I could never fly frontier again that’s how horrible it was!

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

Good for the price. My only complaint is that the pilot should keep the air flowing while passengers are waiting to getting out of airplane.

Book cheap flights from Portland to Caribbean

Recent round-trip flight deals

10/2Wed
1 stopJetBlue
6h 39mPWM-SJU
10/6Sun
1 stopJetBlue
6h 12mSJU-PWM
$270
10/2Wed
1 stopUnited Airlines
7h 25mPWM-SJU
10/5Sat
1 stopUnited Airlines
9h 22mSJU-PWM
$297
6/9Sun
1 stopFrontier
8h 50mPWM-SJU
6/13Thu
1 stopFrontier
9h 14mSJU-PWM
$298
10/2Wed
2 stopsAmerican Airlines
10h 45mPWM-SJU
10/5Sat
2 stopsAmerican Airlines
13h 27mSJU-PWM
$313
8/24Sat
1 stopDelta
7h 05mPWM-STT
8/31Sat
1 stopDelta
8h 39mSTT-PWM
$356
10/29Tue
2 stopsAmerican Airlines
17h 14mPWM-SJU
11/3Sun
1 stopAmerican Airlines
10h 20mSJU-PWM
$362
6/18Tue
1 stopFrontier
28h 02mPWM-PUJ
6/25Tue
2 stopsFrontier
42h 47mPUJ-PWM
$363
6/28Fri
1 stop
13h 16mPWM-SJU
7/5Fri
2 stops
28h 48mSJU-PWM
$468
8/19Mon
1 stopDelta
6h 35mPWM-MBJ
8/26Mon
1 stopDelta
7h 45mMBJ-PWM
$482
6/28Fri
2 stops
26h 46mPWM-SJU
7/5Fri
2 stops
28h 48mSJU-PWM
$489

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Recent one-way flight deals

8/16Fri
2 stopsDelta
10h 59mPWM-MBJ
$141
6/27Thu
2 stopsAmerican Airlines
23h 45mPWM-AUA
$158
11/8Fri
2 stopsAmerican Airlines
41h 38mPWM-AUA
$178
7/6Sat
1 stopJetBlue
6h 48mPWM-SJU
$185
8/16Fri
1 stopAmerican Airlines
20h 15mPWM-MBJ
$197
6/4Tue
1 stopUnited Airlines
10h 36mPWM-MBJ
$218
6/18Tue
1 stopJetBlue
8h 10mPWM-MBJ
$231
6/4Tue
2 stopsDelta
11h 34mPWM-MBJ
$234
6/18Tue
2 stopsAir Canada
27h 50mPWM-MBJ
$275
6/28Fri
2 stopsUnited Airlines
23h 39mPWM-AUA
$345

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Last minute flights from Portland to Caribbean

Last minute flight, train and bus deals

5/31Fri
multi-stopAmerican Airlines
7h 54mPWM-SJU
6/3Mon
multi-stopAmerican Airlines
7h 26mSJU-PWM
$573
5/31Fri
multi-stopAmerican Airlines
14h 12mPWM-SJU
6/3Mon
multi-stopAmerican Airlines
7h 26mSJU-PWM
$574
5/31Fri
multi-stopAmerican Airlines
14h 12mPWM-SJU
6/3Mon
multi-stopAmerican Airlines
17h 17mSJU-PWM
$634
5/31Fri
multi-stop
15h 36mPWM-SJU
6/2Sun
multi-stop
13h 58mSJU-PWM
$809
5/31Fri
multi-stopUnited Airlines
8h 07mPWM-SJU
6/2Sun
multi-stopUnited Airlines
9h 27mSJU-PWM
$827
5/31Fri
multi-stopJetBlue
9h 39mPWM-SJU
6/2Sun
multi-stopJetBlue
9h 55mSJU-PWM
$846
5/31Fri
multi-stop
31h 02mPWM-SJU
6/2Sun
multi-stop
13h 58mSJU-PWM
$964

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