$106 Find Cheap Flights from Portland to Caribbean

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 1/19. 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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Flight Deals

Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$303
Santo Domingo
Santo Domingo2 stops$319
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad2 stops$301
Nassau
Nassau1 stop$322
Kingston
Kingston2 stops$421
Simpson Bay
Simpson Bay2 stops$306
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$297
Puerto Plata
Puerto Plata2 stops$449
Punta Cana
Punta Cana1 stop$303
Santo Domingo
Santo Domingo2 stops$319
Montego Bay
Montego Bay1 stop$332
Oranjestad
Oranjestad2 stops$301
Nassau
Nassau1 stop$322
Kingston
Kingston2 stops$421
Simpson Bay
Simpson Bay2 stops$306
Providenciales
Providenciales1 stop$371
George Town
George Town1 stop$297
Puerto Plata
Puerto Plata2 stops$449

Book Cheap Portland to Caribbean Plane Tickets

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

Wed, Feb 11 - Sat, Feb 21
JetBlue Logo
3:45 pm - 2:55 am
PWM
-
SJU
10h 10m1 stop
JetBlue Logo
6:05 am - 3:37 pm
SJU
-
PWM
10h 32m1 stop
$175JetBlue
Sat, Jan 24 - Wed, Jan 28
United Airlines Logo
2:31 pm - 6:11 am
PWM
-
SJU
14h 40m2 stops
United Airlines Logo
8:10 am - 2:31 pm
SJU
-
PWM
7h 21m1 stop
$212United Airlines
Wed, Apr 8 - Wed, Apr 15
JetBlue Logo
4:51 pm - 12:38 am
PWM
-
SJU
7h 47m1 stop
JetBlue Logo
4:10 pm - 11:59 pm
SJU
-
PWM
7h 49m1 stop
$218JetBlue
Mon, Feb 2 - Fri, Feb 6
American Airlines Logo
5:20 am - 5:03 pm
PWM
-
SJU
10h 43m2 stops
American Airlines Logo
1:58 pm - 11:43 pm
SJU
-
PWM
10h 45m2 stops
$232American Airlines
Sat, Jan 31 - Fri, Feb 6
United Airlines Logo
3:05 pm - 6:11 am
PWM
-
SJU
14h 06m2 stops
United Airlines Logo
2:05 am - 2:39 pm
SJU
-
PWM
13h 34m2 stops
$245United Airlines
Sun, Jan 18 - Fri, Jan 23
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m2 stops
United Airlines Logo
2:05 am - 2:39 pm
SJU
-
PWM
13h 34m2 stops
$250United Airlines
Sat, Feb 28 - Wed, Mar 4
Southwest Logo
2:00 pm - 11:55 pm
PWM
-
SJU
8h 55m1 stop
Southwest Logo
6:10 am - 2:55 pm
SJU
-
PWM
9h 45m1 stop
$256Southwest
Sat, Jan 24 - Wed, Jan 28
Delta Logo
2:35 pm - 11:57 pm
PWM
-
SJU
8h 22m1 stop
Delta Logo
7:00 am - 1:45 pm
SJU
-
PWM
7h 45m1 stop
$276Delta
Mon, Jan 26 - Thu, Jan 29
American Airlines Logo
5:20 am - 4:59 pm
PWM
-
AUA
10h 39m2 stops
American Airlines Logo
2:59 pm - 10:54 pm
AUA
-
PWM
8h 55m1 stop
$301American Airlines
Sat, Feb 21 - Mon, Mar 9
Delta Logo
5:31 am - 12:29 pm
PWM
-
GCM
6h 58m1 stop
Delta Logo
1:12 pm - 11:22 pm
GCM
-
PWM
9h 10m1 stop
$321Delta
Booking Insights

KAYAK's insights & trends for Portland to Caribbean flights

Get data-powered insights and trends into flights from Portland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Portland to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Portland to Caribbean is November, when tickets cost $322 (return) on average. On the other hand, the most expensive months are February and March, when the average cost of round-trip tickets is $627 and $565 respectively.

How far in advance should I book a flight from Portland to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Portland to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Portland to Caribbean, you should book around 2 weeks before departure, which saves you about 30% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$106
Best time to beat the crowds but there is an average 4% increase in price.
Most popular time to fly with an average 23% 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 from Portland to 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 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 from Portland to Caribbean with an airline and back 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 from Portland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the 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
SouthwestOverall score based on 4250 reviews
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

2.0 MediocreMatthew, Jan 2026
DAL - SAN
Read more Southwest reviews

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

It was Delta, but the flight attendants were stressful and disrespectful. I am a diamond member a travel weekly. I have not had a negative thing to share in quite some time. But this was noticeable.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Flight was late from Newark to Atlanta, I asked flight attendant to please let my family of 3 out first when we landed to Atlanta because we were late for our connecting flight to Quito. She didn't and we were late for 5 minutes we couldn't board the plane and spend hours trying to get another flight with customer service for the next day.

I really liked the legroom. I am 6’4”.a at For some reason our seats were not together and using the app to fix it didn’t work. Passengers were nice enough to move for us but you should absolutely ensure a parent sits with their child.

Late delayed flight delays boarding and delays leaving and delays on arrival too. Cramped plane no room no food.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Some flight attendants were great others were cranky. Seats were very tight and sitting on an aisle was very hard as the carts and people walking constantly bumped shoulder and arm.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

The staff was hospitable and professional. The seat had a bit of wear. The winner shade was stuck 1/4 open. I received the best of both worlds. The morning sun was able to come in and blind the screen i was trying to use while at the same time it was too low to look out and enjoy the view. Rather embarrassing for a 1st class ticket.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

The flight was delayed by two de-icings. The seatbelt did not work correctly. It did not stay tight.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

Aircraft was noisy, old and never dimmed the lights on a night flight even on business class! I flew 17 times on United and probably another 40 on other airlines United USA /Europe flights were the worst to include luggage delayed once going to europe and once coming back

Good food & refreshment. The seats and entrainment screens are modern compared to others. The staff though pleasant serve and attend to passengers based on nationality. Some get served first others last regardless of their seating positions.

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

The flight was on time and arrived early. The crew were friendly and helpful.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

The economy seats are very cramped and the food was bizarre. However, I did like the greek yogurt option for breakfast.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

Nothing to write home about, average flight experience. Seats were spacious enough, crew friendly enough. Loved the AA entertainment/wifi service.

Kayak was among the missing. There was not the usual advice regarding next gate after arriving in Dallas. No communication after the reminder to check in before the Moline flight. What happened?

They should have allowed for extra time to de-ice the plane before boarding passengers. This delayed us about 10-15 mins after we boarded. Overall experience was fine. Crew was friendly and on top of everything. We didn’t have any issues during the flight.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports