$138 Find Cheap Flights from Portland to Caribbean Islands - Compare and Save

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 Islands departing on 1/11. 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.
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Cheap Flights from Portland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$400
Santo Domingo
Santo Domingo1 stop$447
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$494
Nassau
Nassau1 stop$368
Kingston
Kingston1 stop$472
Simpson Bay
Simpson Bay2 stops$485
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata1 stop$635
Punta Cana
Punta Cana1 stop$400
Santo Domingo
Santo Domingo1 stop$447
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$494
Nassau
Nassau1 stop$368
Kingston
Kingston1 stop$472
Simpson Bay
Simpson Bay2 stops$485
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata1 stop$635

Book Cheap Portland to Caribbean Islands 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 Islands 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 Islands

Sat, Oct 24 - Thu, Oct 29
American Airlines Logo
7:26 pm - 2:55 pm
PWM
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STT
19h 29m
2 stops
American Airlines Logo
3:46 pm - 11:03 am
STT
-
PWM
19h 17m
2 stops
$280American Airlines
Sat, Oct 24 - Thu, Oct 29
American Airlines Logo
7:26 pm - 2:55 pm
PWM
-
STT
19h 29m
2 stops
American Airlines Logo
3:46 pm - 11:03 am
STT
-
PWM
19h 17m
2 stops
$280American Airlines
Tue, Oct 20 - Mon, Oct 26
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
United Airlines Logo
1:35 pm - 11:59 pm
SJU
-
PWM
10h 24m
2 stops
$352United Airlines
Fri, Oct 23 - Mon, Oct 26
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
United Airlines Logo
4:50 pm - 11:59 pm
SJU
-
PWM
7h 09m
1 stop
$352United Airlines
Thu, Oct 22 - Mon, Oct 26
Delta Logo
6:01 am - 4:49 pm
PWM
-
SJU
10h 48m
1 stop
Delta Logo
6:45 am - 3:35 pm
SJU
-
PWM
8h 50m
1 stop
$352Delta
Wed, Nov 18 - Mon, Nov 23
Delta Logo
6:00 am - 2:20 pm
PWM
-
SJU
7h 20m
1 stop
Delta Logo
2:05 pm - 11:55 pm
SJU
-
PWM
10h 50m
1 stop
$352Delta
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
3:25 pm - 11:20 pm
PWM
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SJU
6h 55m
1 stop
Southwest Logo
5:35 am - 1:05 pm
SJU
-
PWM
8h 30m
2 stops
$421Southwest
Wed, Nov 11 - Sun, Nov 15
Southwest Logo
10:25 am - 10:20 pm
PWM
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SJU
10h 55m
2 stops
Southwest Logo
5:35 am - 4:30 pm
SJU
-
PWM
11h 55m
2 stops
$421Southwest
Wed, Nov 11 - Sun, Nov 15
Multiple Airlines Logo
6:31 pm - 12:57 am
PWM
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SJU
29h 26m
1 stop
Multiple Airlines Logo
7:42 pm - 9:08 am
SJU
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PWM
14h 26m
1 stop
$472Multiple Airlines
Tue, Nov 10 - Sun, Nov 15
Multiple Airlines Logo
5:09 pm - 12:04 pm
PWM
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SJU
17h 55m
2 stops
Multiple Airlines Logo
7:42 pm - 9:08 am
SJU
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PWM
14h 26m
1 stop
$486Multiple Airlines
Booking Insights

KAYAK's insights & trends for Portland to Caribbean Islands flights

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

Can I save money by flying with a layover from Portland to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $383, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Portland to Caribbean Islands, 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 Islands is January, when tickets cost $468 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $698 and $662 respectively.

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

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 Islands, 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 Islands, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

Cheapest flight

$138
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Portland to Saint Thomas Island

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Portland to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Portland to Caribbean Islands? 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 4224 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

6.0 GoodJeremy, Aug 2026
STL - PHL
Read more Southwest reviews

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

Boarded the plane in Portland and sat on the tarmac for four hours before being given clearance to take off. Apparently a "scratch" was detected on the preflight inspection. This delay resulted in me missing my connection in Baltimore. I therefore had to stay overnight and then catch an early flight this morning, which resulted in my missing a mandatory class. I would like a refund / voucher to cover the cost of the missed flight. And additional voucher for the time spent on the plane in Portland would also be appreciated.

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

Comfortable seats. Nice service online. Short flight, so not a lot of time to enjoy.

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

The flight was done by SkyWest only WIFI no entertainment center are available on the CRJ

Your survey needs a N/A option. I didn’t use the entertainment or eat food.

The flight was over 2 hours late.. once we finally got boarded things were fine

Delta did an awful job w logistics at DTW. Missed connection. We were there an hour early. SUCKED

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

Both my flight where delayed Had 25min to make it to my transfer flight

I just got back from a trip with 3 flights each way. The flights were good and we were happy with out experience. There was one steward on our first flight that was harsh and grump with passengers. It did not leave a good impression. All of the other flight crews were great on the other five flights.

They changed my flight 5 hours before it took off and changed my connecting airport messing up my entire 1st day in Japan.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The crew and the pilots. The pilots were amazing. The landing in Cancun was excellent.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

Didn’t happe- would have missed connection so we rebooked

Both directions of our trip were befuddled by massive delays, one of which led to our connecting flight being grounded mid air due to storms that we’d have missed if we were on time. The other our originating flight was delayed repeatedly until it arrived at our connecting airport later than our final leg was even supposed to have arrived. American cannot seem to manage rebooking s for a family party… both directions we had to come up with a plan to get to Boston stay overnight only one night each direction was covered by the airline -and take a bus to or from our destination. Missed an entire leg of our trip, hotel cancellation fees, expensive stay in Boston and bus ticket expenses are unlikely to be comped and the meal vouchers are worthless.

The flight was delayed 4 hours, and when we finally boarded, they told us that the fuel was only just then checked. So, we waited even longer to take off.

With a 24 hour delay, the Flight stared off rough. They had a nationwide IT Outage but communications to Passengers was very bad. Ground Staff and Ticket Agents were extremely rude and unhelpful. Perhaps they should take ground training from DL or Qatar. The food was horrible. Seafood was mixed with Bacon. Those two don’t have any space for Jewish or Muslim Faith Customers. The Airline needs new management.

Great. Clean. Seats comfortable. Food was free. Had new release movies.

The airplane I love and I love I came back safe thank you American airlines

My flight was 4 hours delayed on departure at 6a causing me to miss my connection at DCA. I had to scramble to find a seat home on a later flight and instead of an exit seat, I was in row 30 on a flight getting me home 5 hours later than planned. The AA team on the ground did a fine job. AA continues to run the airline like the passengers are cargo.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Flight was delayed after boarding and no idea when it would take off. Crew in Portland did arrange for transport to Boston for a different set of flights to my destination.

Seats are so close together. Middle seats should be discounted.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports