$153 Find Cheap Flights from Portland to Caribbean - Compare and Save

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Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$360
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad1 stop$410
Nassau
Nassau1 stop$346
Kingston
Kingston2 stops$754
Simpson Bay
Simpson Bay2 stops$430
Providenciales
Providenciales1 stop$427
George Town
George Town1 stop$472
Puerto Plata
Puerto Plata2 stops$955
Punta Cana
Punta Cana1 stop$360
Montego Bay
Montego Bay1 stop$375
Oranjestad
Oranjestad1 stop$410
Nassau
Nassau1 stop$346
Kingston
Kingston2 stops$754
Simpson Bay
Simpson Bay2 stops$430
Providenciales
Providenciales1 stop$427
George Town
George Town1 stop$472
Puerto Plata
Puerto Plata2 stops$955
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?

The cheapest month for flights from Portland to Caribbean is January, when tickets cost $426 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $729 and $707 respectively.

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

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 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

September

Cheapest flight

$153
Best time to beat the crowds but there is an average 26% increase in price.
Most popular time to fly with an average 15% 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 4219 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

8.0 ExcellentTiffany, Nov 2026
Read more Southwest reviews

My return flight was much better than the flight there! I paid for seat to Veagas but not the return. Thankgoodness they assigned me a seat with additional leg room as I have back and leg problems. I really appreciate it. With the flight already being super expensive due to gas prices and having to pay for bags (now) I needed to save some money.

My first flight from LGA to STL was not good. They didn't do service until over halfway through the flight, the internet didn't really work, and the crew all seemed like they didn't want to be there.

We were stressed about landing as our connecting flight was about to start boarding, being unfamiliar with the airport or where the gates were. We exited the plane to discover we were at the gate we needed. We would be getting back on the same plane but nobody told us we could have just stayed onboard. My wife and I were seated on aisle seats across from each other. We asked if there was a way we could sit together. Once we were at cruising altitude they let us move to an unoccupied row so that was nice.

It’s Southwest. The seats are small, the snacks are meh, it’s $50 to check a bag. It’s exactly fine. Could have been better. Could have been worse. It’s not Spirit

They delayed my flight all day but didn't try to reschedule me until all other options were gone. Ended up on a red eye. Not happy. Lesson learned, don't book the last flight from SJC to RDU.

Every single flight I take with southwest is delayed by at least one hour. Unbelievable

When I made my reservation it would have been nice if kayak would have included my luggage. Unaware that I had to pay $45 each way. Should have asked at reservation time if luggage was being checked

Crew was a little surly. But plane left on time and arrived early. All one can ask for. New 737 Max was nice.

Flight was delayed about 50 minutes and completely full. they did the usual demand for people to check carry-ons. they called all groups to board very fast only to stand in the gangway after having boarding passes scanned. Why don't airlines board from the back to front - since they now have assigned seats? our stewardess got drink orders confused, so she just called out "cranberry". etc.,.. I wish they wouldn't serve pretzels snacks with a powdered coating, as it sticks to your hands and they don't have wet wipes. don't want to lick my fingers after hanging out in the terminal for over an hour.

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.

A 6hr delay is going to put a damper on all reviews. It was almost impossible to get into the Delta club also. Zero conveyance. I could not use my status for anything. Makes me wonder why am I loyal to delta?

I fly coach so there is always the feeling everyone up front has more space than me. Everything was fine - on time which is the most important thing!

Great overall experience and use of the Delta One lounge was amazing!

I used by Skymiles to upgrade to First so that I could comfortably work using my laptop. But WiFi was intermittent and unavailable for long periods. I feel like I wasted 70,000 miles :(

Great as one can be for a one connection 6 hour flight

Packed flight and not sure why dinner service would start at midnight while passengers we’re trying to sleep

The gate attendant was not clear w message on flight delays.

Chairs don’t recline and the ones that do recline, barely do recline. It was most uncomfortable flight i ever been on.

Good but not on par when compared with foreign flag carriers.

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

Tiny seat made for midgets. You can’t put a normal size human in such a tiny seat for 8 god damn hours! Hot plane, no air. Lost bags at Rome airport for 8 hours, lucky to have found them. Horrible flying experience, United Airlines should be embarrassed!

The issue is the flight is delayed, which causes me Missing the connecting flight by 3 mins. Remember the connecting flight is a US codeshare flight so UA should be able to inform the operating airline about the delay.

Seats are made for children. An 8 hour flight with tiny seats is more like a cattle car. Lost bags at Rome airport caused a 7 hour delay.

We sat on the tarmac in Denver for over 30 minutes because a plane was in our gate. The pilot kept saying it will just be 5 minutes or less. However, we sat for over 30 minutes. Experiences like this make customers not trust what the pilot is saying.

Waited on tarmac for approximately 15-25 minutes before taking off. When landing, the time it took to taxi to our gate was the also 15-25 minutes.

Waited on tarmac to take off for approximately 15-25 minutes. When landing, the taxi to our gate took a similar amount of time. This happened on both of my United flights.

The plane was so old. I paid a ridiculous amount to fly business and there was no internet for six hours! This can't be happening in 2026 and especially in cross country flights where there are a high volume of business travelers.

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.

Both ways the people in the rear section of the plane were forced to check their carry on bags. I would understand this if the size and number of bags were not limited, but I do not understand why there is not room for one small overhead bag per person, even if the flight is full. I could watch the baggage handlers loading the extra luggage from my window and I’m pretty sure mine wouldn’t have survived undamaged, even though it is new and sturdy.

You sent me a confirmation yesterday for a flight reservation today that I never made. What is going on?????

Entertainment, clean plane and funny pilot over the intercom was excellent… however, gate agent was rude and was probably a Spirit employee before they went bankrupt… there were 3 flight attendants - 2 of them didn’t want to be there the other one was kind and nice… I want you to recognize how you have to compete with Delta or South West airlines or even American Airlines which would choose over you at any given day from here on out. Please treat people respectfully. If you hate working in this industry - go and work somewhere else. The flight was very empty and it shouldn’t be hard to crack a smile once in a while. Very disappointing… I remember flying Jet Blue back in the day from Dulles IAD to LAX and you guys were super cool and fancy and made flying fun again - truly elevated the experience. Don’t become the next most hated airline… you can do better . I want you to succeed…

Free wifi was almost impossible to get, kept dropping the connection

Not good - we boarded and taxied for an hour before they told us there were technical issues with the plane. They told us we were going to need to deplane, parked back at the gate but then didn’t tell us we didn’t have to anymore. There was just a lot of uncertainties with poor communication.

3.5 hour delay because of “mundane” mx issue. Aircraft had to be towed 3 times.

Overall great experience, though my screen for entertainment was not working and I could see that others were.

Plane was very comfortable,ore legroom, help yourself snack are so weren't disturbed by staff passing up and down cabin, gluten free food availability and really efficient and friendly staff . Boarding and good to time. Highly recommend t

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

What's not to like? Value?definitely. Every JetBlue member was extremely friendly on this flight. Very very nice new-ish aircraft,plenty of room. GOOD coffee. Entertainment,I didn't need it,but I think its available. What to do better? Well,there's nothing we can do about the other people, unbelievable how some folks are operating. Just don't allow people to lug all their stuff onto the aircraft. 1 bag. That's it. Be easier for you too. I personally would enjoy more options in schedule. One flight in and out a day is warranted given the local,I understand, but the times are inconvenient. Again, I completely understand why it is that way,It would however be great to have different options.

This flight left LAX on time and arrived early in HNL. The flight crew was excellent, no issues with service or attentiveness. My issue is with the A321neo ... First class should be renamed business class as the seats are not that comfortable. And, having to use my phone as the entertainment device is just not acceptable ... I'm not going to carry a tablet so I can watch a movie. The music choices are limited, at least IMO.

Seats are getting smaller and smaller. In flight movies are poor compared to other airlines. Food is mediocre.

There was a 4 hour delay, some of which was attributed to ATC weather but started with maintenance and then later also log books. Though the flight went far beyond the scheduled time, there were no accommodations such as additional meal options or anything else.

My flight left Honolulu EIGHT hours late due to lack of flight crew. This was the second time in 2026. The first class staff were excellent ... personable and friendly. The food was okay ...

The food in first class has taken a big downturn

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.

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.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental