$138 Find Cheap Flights from Portland to Caribbean - 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 departing on 8/14. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$422
Santo Domingo
Santo Domingo1 stop$544
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$433
Nassau
Nassau1 stop$420
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$423
George Town
George Town2 stops$372
Puerto Plata
Puerto Plata1 stop$581
Punta Cana
Punta Cana1 stop$422
Santo Domingo
Santo Domingo1 stop$544
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$433
Nassau
Nassau1 stop$420
Kingston
Kingston1 stop$466
Simpson Bay
Simpson Bay2 stops$380
Providenciales
Providenciales1 stop$423
George Town
George Town2 stops$372
Puerto Plata
Puerto Plata1 stop$581

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, 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
Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
7:26 pm - 2:55 pm
PWM
-
STT
19h 29m
2 stops
American Airlines Logo
2:01 pm - 9:36 pm
STT
-
PWM
8h 35m
1 stop
$280American Airlines
Tue, Sep 22 - Mon, Sep 28
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
United Airlines Logo
1:00 am - 9:08 am
SJU
-
PWM
8h 08m
1 stop
$352United Airlines
Tue, Sep 22 - Mon, Sep 28
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
United Airlines Logo
1:00 am - 2:38 pm
SJU
-
PWM
13h 38m
2 stops
$352United Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:00 am - 4:49 pm
PWM
-
SJU
10h 49m
1 stop
Delta Logo
7:30 am - 1:54 pm
SJU
-
PWM
6h 24m
1 stop
$352Delta
Thu, Nov 19 - Thu, Nov 26
Delta Logo
6:00 am - 5:20 pm
PWM
-
SJU
10h 20m
1 stop
Delta Logo
2:05 pm - 11:55 pm
SJU
-
PWM
10h 50m
1 stop
$352Delta
Fri, Oct 30 - Fri, Nov 6
Southwest Logo
3:25 pm - 1:20 am
PWM
-
SJU
9h 55m
2 stops
Southwest Logo
5:35 am - 4:30 pm
SJU
-
PWM
11h 55m
2 stops
$363Southwest
Fri, Oct 30 - Fri, Nov 6
Southwest Logo
5:30 pm - 12:05 am
PWM
-
SJU
6h 35m
1 stop
Southwest Logo
5:35 am - 1:05 pm
SJU
-
PWM
8h 30m
2 stops
$363Southwest
Sat, Oct 10 - Fri, Oct 16
Multiple Airlines Logo
5:09 pm - 1:53 am
PWM
-
SJU
32h 44m
2 stops
Multiple Airlines Logo
4:39 pm - 5:51 pm
SJU
-
PWM
25h 12m
1 stop
$403Multiple Airlines
Wed, Nov 18 - Tue, Nov 24
Multiple Airlines Logo
5:09 pm - 2:16 pm
PWM
-
SJU
20h 07m
2 stops
Multiple Airlines Logo
6:00 am - 4:24 pm
SJU
-
PWM
11h 24m
1 stop
$499Multiple Airlines
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 January, when tickets cost $456 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $696 and $685 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 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 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 4227 reviews
8.1Boarding
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

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

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

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.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

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.

Flight was delayed for about an hour but overall good experience

Staff is friendly and helpful but flight was delayed by one hour from Detroit, making for tight window in Toronto to clear Canada Customs and pass through security screening in order to get to connecting flight on time.

Delta staff was exceptionally helpful and considerate. However, the first two of three flight legs were delayed making connections tentative and stressful.

Delta is always late. Ruined our first day of a short vacation. Timing is important. We pay to stay on an itinerary

First flight was delayed which resulted in missing our connecting. As a result class was downgraded to economy on a later flight.

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

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

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.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

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.

The ground closures and flight delays were unwelcome. I think the captain did what he could to manage expectations for the delays, but the stress level increasing in the cabin was palpable with every announcement. It may be obvious to those who fly frequently, but if the ground is closed for us to get to a gate, it's also closed for connecting flights to leave. Other passengers were so stressed they were rude. A bit further explanation could have helped.

Horrible. No AC. No Air inside the plane. We had to deplane twice! It is late almost 5 hrs in total. I almost passed out and about to call 911. I asked the crew to be honest and open the door. The lady next to me was lay down in the floor due to heat and no air inside the plane. I got headaches, can’t wait the replacement flight about midnight Dallas time. I end it up rebook for next day flight and stay overnight using my own pocket in a hotel nearby due to headaches and can’t breath. I still have a headache this morning. Still not decided yes how to file this issue to AA and/or FAA.

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Flight was delayed for 5 hours in ten minute increments. Bizarre and frustrating

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

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.

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

The flight was delayed. I upgraded to more room. I can't imagine how small the regular seats are I haven't upgraded for my return flight yet.

see my previous response about being kicked off the flight and having to fly the next day, ruining a planned vacation tour.

Horrible - for the first time in my life i was denied boarding an international flight because the name used on my ticket - Josh - was not exactly the same as my passport - Joshua. At no time during ticketing, online check-in, or at the airport flying from Boston to NY was i notified of a problem. It was only at boarding from NY to Costa Rica I was informed of the problem and by then it was too late. After missing the flight I was told by airport Jet Blue staff, including a supervisor, that it was my problem and they could not assist because i bought "the cheapest fare". i was hung up on twice by JetBlue customer service, including once by a supervisor. I blame Kayak and your awful partner ChatDeal for even allowing me to purchase an international ticket without verifying this - you effectively sold me a ticket i could not use. Shame on you and shame on ChatDeal for doing nothing to help me resolve the situation. What a scam.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports