$87 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 3/16. 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
1 adult, Economy, 0 bags

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Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$306
Santo Domingo
Santo Domingo2 stops$318
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad2 stops$304
Nassau
Nassau1 stop$325
Kingston
Kingston2 stops$420
Simpson Bay
Simpson Bay2 stops$298
Providenciales
Providenciales1 stop$348
George Town
George Town2 stops$301
Puerto Plata
Puerto Plata1 stop$448
Punta Cana
Punta Cana2 stops$306
Santo Domingo
Santo Domingo2 stops$318
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad2 stops$304
Nassau
Nassau1 stop$325
Kingston
Kingston2 stops$420
Simpson Bay
Simpson Bay2 stops$298
Providenciales
Providenciales1 stop$348
George Town
George Town2 stops$301
Puerto Plata
Puerto Plata1 stop$448

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

Sat, Apr 25 - Wed, Apr 29
United Airlines Logo
9:30 am - 9:24 pm
PWM
-
SJU
11h 54m2 stops
United Airlines Logo
1:00 am - 8:44 am
SJU
-
PWM
7h 44m1 stop
$211United Airlines
Mon, Feb 2 - Fri, Feb 6
American Airlines Logo
3:58 pm - 11:56 pm
PWM
-
SJU
6h 58m1 stop
American Airlines Logo
1:58 pm - 11:43 pm
SJU
-
PWM
10h 45m2 stops
$231American Airlines
Wed, Feb 25 - Wed, Mar 4
JetBlue Logo
4:45 pm - 1:45 am
PWM
-
SJU
8h 00m1 stop
JetBlue Logo
6:05 am - 3:50 pm
SJU
-
PWM
10h 45m1 stop
$274JetBlue
Tue, Feb 10 - Fri, Feb 27
Delta Logo
5:30 am - 5:17 pm
PWM
-
SJU
10h 47m1 stop
Delta Logo
6:02 pm - 12:18 am
SJU
-
PWM
7h 16m1 stop
$275Delta
Sat, Feb 7 - Thu, Feb 26
Multiple Airlines Logo
6:18 pm - 12:34 am
PWM
-
SJU
29h 16m1 stop
Multiple Airlines Logo
4:22 pm - 10:49 am
SJU
-
PWM
19h 27m1 stop
$282Multiple Airlines
Mon, Jan 12 - Thu, Jan 15
United Airlines Logo
3:12 pm - 12:36 am
PWM
-
SJU
8h 24m1 stop
United Airlines Logo
2:05 am - 9:01 am
SJU
-
PWM
7h 56m1 stop
$294United Airlines
Tue, Mar 3 - Tue, Mar 3
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m1 stop
United Airlines Logo
2:05 am - 3:14 pm
SJU
-
PWM
14h 09m2 stops
$296United Airlines
Thu, Jan 29 - Tue, Feb 3
American Airlines Logo
3:58 pm - 1:42 pm
PWM
-
SXM
20h 44m2 stops
American Airlines Logo
5:33 pm - 12:05 pm
SXM
-
PWM
19h 32m2 stops
$298American Airlines
Wed, Feb 11 - Wed, Feb 25
Delta Logo
5:30 am - 2:31 pm
PWM
-
SJU
8h 01m1 stop
Delta Logo
7:00 am - 1:43 pm
SJU
-
PWM
7h 43m1 stop
$301Delta
Tue, May 5 - Wed, May 20
JetBlue Logo
6:00 am - 1:03 pm
PWM
-
PLS
7h 03m1 stop
JetBlue Logo
2:24 pm - 11:36 pm
PLS
-
PWM
9h 12m1 stop
$348JetBlue
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 April, when the average cost of round-trip tickets is $610 and $571 respectively.

What’s the cheapest day of the week to fly from Portland to Caribbean?

The average price of all round-trip flights from Portland to Caribbean clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Portland to Caribbean. For your return ticket, we recommend flying on a Thursday and avoiding Tuesdays for the best deals.

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$87
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $302 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $557.

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 4256 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

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.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

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.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Sat next to a one year old. She crawled all over the place and made me laugh.

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

Gate agent at Frankfurt was terrible. She denied PRE boarding even as it was printed on the boarding pass. Refused to look at the boarding pass and literally shouting for no reason. Frankfurt airport has horrible and rude staff who avoids trying to answer any question at all. Overall, horrible experience.

The Crew and the food was the worst I ever had in Business Class. First they told us there were no space for carry on. It was plenty of space over our 2 row seats, we had to ask to let us travel with it which was accepted. They were aware that we had to run for the connection due to the previous flight delay. Have us one hour waiting for more customers and not even offer a glass of water. Then started the service and they started to serve other passengers drinks in business and did not offer any drinks until they serve our pre ordered meal and I ask for something to drink. I had to wait until they finished to serve all passengers until Inget something. The crew was the worts I ever had for Business Class in my life.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

I don’t know who decides what food to serve on these flights but I would be so embarrassed if I served this to anyone and call it food…

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

The pilot greased the landing and the crew was fantastic.

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.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports