$126 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 7/23. 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$392
Santo Domingo
Santo Domingo1 stop$526
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad1 stop$351
Nassau
Nassau1 stop$333
Kingston
Kingston2 stops$439
Simpson Bay
Simpson Bay2 stops$427
Providenciales
Providenciales1 stop$539
George Town
George Town2 stops$384
Puerto Plata
Puerto Plata1 stop$694
Punta Cana
Punta Cana1 stop$392
Santo Domingo
Santo Domingo1 stop$526
Montego Bay
Montego Bay1 stop$324
Oranjestad
Oranjestad1 stop$351
Nassau
Nassau1 stop$333
Kingston
Kingston2 stops$439
Simpson Bay
Simpson Bay2 stops$427
Providenciales
Providenciales1 stop$539
George Town
George Town2 stops$384
Puerto Plata
Puerto Plata1 stop$694

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

Mon, Nov 23 - Thu, Dec 3
American Airlines Logo
6:39 pm - 4:55 pm
PWM
-
STT
21h 16m
2 stops
American Airlines Logo
6:17 pm - 11:37 am
STT
-
PWM
18h 20m
2 stops
$260American Airlines
Wed, Oct 28 - Mon, Nov 2
American Airlines Logo
4:54 pm - 12:58 pm
PWM
-
STT
20h 04m
2 stops
American Airlines Logo
4:18 pm - 11:49 am
STT
-
PWM
20h 31m
2 stops
$265American Airlines
Wed, Nov 18 - Tue, Nov 24
Delta Logo
2:35 pm - 11:55 pm
PWM
-
SJU
8h 20m
1 stop
Delta Logo
1:55 pm - 10:23 pm
SJU
-
PWM
9h 28m
1 stop
$322Delta
Sat, Nov 7 - Sat, Nov 14
United Airlines Logo
7:43 pm - 12:13 pm
PWM
-
MBJ
16h 30m
1 stop
United Airlines Logo
3:20 pm - 11:23 pm
MBJ
-
PWM
8h 03m
1 stop
$324United Airlines
Fri, Oct 2 - Tue, Oct 6
United Airlines Logo
7:25 pm - 11:43 am
PWM
-
MBJ
17h 18m
2 stops
United Airlines Logo
12:52 pm - 10:40 am
MBJ
-
PWM
20h 48m
2 stops
$329United Airlines
Mon, Nov 16 - Fri, Nov 20
Delta Logo
6:00 am - 1:30 pm
PWM
-
NAS
7h 30m
1 stop
Delta Logo
1:00 pm - 11:49 pm
NAS
-
PWM
10h 49m
1 stop
$333Delta
Fri, Oct 30 - Fri, Nov 6
Southwest Logo
3:25 pm - 12:20 am
PWM
-
SJU
8h 55m
2 stops
Southwest Logo
5:35 am - 4:30 pm
SJU
-
PWM
11h 55m
2 stops
$363Southwest
Wed, Oct 14 - Tue, Oct 20
JetBlue Logo
6:00 am - 3:56 pm
PWM
-
SJU
9h 56m
1 stop
JetBlue Logo
10:50 am - 11:52 pm
SJU
-
PWM
13h 02m
2 stops
$374JetBlue
Thu, Oct 8 - Wed, Oct 14
Southwest Logo
5:20 am - 12:15 pm
PWM
-
SJU
6h 55m
1 stop
Southwest Logo
5:50 am - 3:30 pm
SJU
-
PWM
9h 40m
1 stop
$390Southwest
Mon, Aug 24 - Fri, Aug 28
JetBlue Logo
6:00 am - 11:58 pm
PWM
-
SJU
17h 58m
2 stops
JetBlue Logo
12:50 pm - 12:25 am
SJU
-
PWM
11h 35m
2 stops
$392JetBlue
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 February, when tickets cost $101 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $308 and $298 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 seasonSeptember
Cheapest flight$126
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 15% increase in price.
Flight from Portland to Nassau

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 4249 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

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

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

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

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

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 and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

No Internet, no backseat screen, no nothing. I bought a Delta ticket and ended up on American Airlines. How did that happen?

Very good seat and service. No complaints about the food. Take off delayed due to airport traffic

It is usually very pleasant. Good service for the price, international flights are even better

We never made it on this flight because we missed our connection due to o delayed flight from Jackson.

We had a terrible experience. The flight was delayed several hours, so we missed our connection. We were told to wait at the airport. At around 11:00 pm, the flight was cancelled. There were no available seats out of Jackson for the next two days. Fortunately, we had the foresight to rebook on United for the next day. However, we had to spend a long day at the airport and an overnight at a mediocre hotel. It was a miserable way to spend part of our vacation. We also sacrificed our $450 deposit on our California hotel because we could not get there.

delta wifi wouldn’t work boarding was not in sequence flight crew spent most of their time on the phone with the lights off pretending no one wanted or needed anything

Everything worked smoothly, never had a concern with the flight from start to finish.

Friendly flight attendant Quick checking for baggage drop Quick TSA lines

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

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

Flight was delayed “due to earlier delays of that plane”, so we were nearly three hours late.

There was a piece of plastic baked into my buttermilk biscuit! I have a pictures. The flight attendants in first class were really apologetic, and tried to rectify the situation. I I am very appreciative that they were able to give me some packets of pretzels and gummy bears. I understand they don't personally handle the food until warming it up so I know it wasn't their fault. I don't know whether it was a newer aircraft, or different food packaging, but I was happy that when the food was being warmed up - it didn't smell like plastic. Jokes on me with finding plastic in my food.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

The seats were very uncomfortable. I paid for the front economy. i swear they added a row of seats in there. It was so tight, that I could measure the distance between my seat and the one in front from my elbow to the tips of my fingers plus six inches. The seat cushion was completely worn out. The dinner was very good. Thank you for having a vegetarian option as a standard. But breakfast was nothing but sugar. that's not food. The crew was crabby and rude, especially in regards to coming to the back gallery. And the entertainment choice: why would you put violent movies on the choice? the Godfather? Some movies with black women being beaten over the head with clubs? What the heck? You know that when there is a movie on a plane, everyone gets to watch it. Why choose the most violent titles possible? The total number of movies were very limited, and the television, even more so. No games were available on the set. The wellness section was nice, thank you. I appreciated a galley in the middle where I could stand. The seats were unbearable.

The seats were uncomfortable, as if the cushions haven't been switched out in many years. I felt like I was on an old bus. The food was delicious. thank you. Onboard entertainment, very limited. Unless you like violent movies. Why in the world would you have such severely violent movies on a plane? if you don't want to see such things, you don't have a choice. Have you considered that when choosing entertainment? Good god. Why would you have the Godfather? Or black women being brutally beaten with a club? Why in the hell would you put that kind of material on a plane? As for Kayak: Why when I ordered Qantas, was the plane on United?

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.

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

It’s love good long way travel!! I always want more give me price down i want ever month travel I miss travel only North Carolina to Thailand in my love her !!

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

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.

I just for my TSA. So security line is short and upgraded to one group up. I do think the ground crew should learn new way of boarding - the passengers sitting in higher number seat should board first to prevent traffic jam.

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports