$108 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 Cana2 stops$355
Montego Bay
Montego Bay2 stops$358
Oranjestad
Oranjestad1 stop$340
Nassau
Nassau1 stop$328
Kingston
Kingston2 stops$651
Simpson Bay
Simpson Bay2 stops$310
Providenciales
Providenciales2 stops$486
George Town
George Town2 stops$422
Puerto Plata
Puerto Plata1 stop$840
Punta Cana
Punta Cana2 stops$355
Montego Bay
Montego Bay2 stops$358
Oranjestad
Oranjestad1 stop$340
Nassau
Nassau1 stop$328
Kingston
Kingston2 stops$651
Simpson Bay
Simpson Bay2 stops$310
Providenciales
Providenciales2 stops$486
George Town
George Town2 stops$422
Puerto Plata
Puerto Plata1 stop$840
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 $423 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $732 and $696 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 24% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low season

September

Cheapest flight

$108
Best time to beat the crowds but there is an average 31% increase in price.
Most popular time to fly with an average 20% increase in price.
Flight from Portland to Simpson Bay

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.
7.9
SouthwestOverall score based on 4214 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

6.0 GoodRobert, Oct 2026
Read more Southwest reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

Stop asking fir people to check carry on and then bind are free. Then the wait to get your luggage is ridiculous. This particular flight came with a 45 min wait, after waiting in tarmac waiting for a gate inhaling jet exhaust. And how about those landings?! Do the pilots not know the earth is coming up under the descending plane?! This is the only airline I get sick on. Every. Time.

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.

Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Delayed for no reason at all originally. Then they said it was due to weather conditions. Communication between kayak and Southwest was terrible because both displayed different delays and departure times for HOURS throughout the day. The plane then had technical issues which delayed us from taking off even longer. Didn’t actually take off until 11:45pm when the original departure time was 7:35pm. I didn’t get home until 1:30am the next day. I was exhausted and pissed off. I am not confident if I’ll fly southwest in the future or use kayak to book.

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.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

13 hour delay stuck in Detroit and missed a day of meetings. It was terrible

My flight was so delayed I would’ve missed my connection and had to cancel my trip

Seemingly unnecessary delays were compounded by a lack of communication from the flight crew which turned a four hour delay into an overly stressful experience.

I like Delta. I dislike the volume of announcements from the crew. They are not always easy to hear and typically repetitive.

I think the crew makes way too many announcements that are: 1) hard to hear in some cases and 2) repetitive. This detracts from entertainment and concentration if working or reading.

Everything was great. The only thing that wasn’t was the breakfast calzone which was basically warm bread. It was very tasteless and wasn’t good at all

Great crew. Comfortable seating. Nice overhead bin space. My app didn't allow me to check in for my flight to BOS. When I called Support, they didn't fix it, but just told me to check in at the airport. Seat back entertainment was great. Could be better if the audio could connect to Bluetooth.

It was the hottest flight I’ve been on in a long time. The female flight attendants were not nice.

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

Premium economy was worth it. Great seats and good food.

Food was good. Clean aircraft. But why do the airlines make the seats so narrow?! Your executives should have ride in a seat so restrictive for 11 hours and see how miserable it is! When.we got to MUC they changed my boarding gate 3 times for my next flight!!!!

Good flight, even though there was a delay, still got back on time

Santa Barbara is a super small and easy airport. Breezed through rental car return, breezed through Security, ordered a coffee and muffin and to my gate in less than 30 minutes. Maybe because it was a small airport we got the oldest plane. Hardly any overhead space and absolutely zero internet. Its NFL Sunday man! That hurt.

We were delay because so many bags needed to be gate checked and it was disappointing not to have outlets in the seats for such a long flight.

There were no vegan options for first class. Even though we were promised the satellite internet for free, we received NO wifi at all. Even though we were promised a 20-min early arrival, we ended up over 30 mins late.

No water or beverage was provided. I had to ask for water. The sole flight attendant had more interest in selling the credit card. In addition when we got to Dulles the plane and gate were misaligned and it took at least 15 minutes to get off the plane.

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.

There was more leg room in what was most likely a basic assigned seat (row 25) then on other airlines I've flown lately.

They lost my luggage and have ruined first day of my vacation. Still don’t have it. I have nothing. I also paid for a seat I did not get. They changed both our seats with no notice. Will never fly this airline again.

My overall experience with JetBlue was pretty poor and disappointing. We originally booked a DIRECT flight home from Boston on 9/28 at 8:00pm even though it cost more than the non direct flights. With no reason other than "unforeseen circumstances", our flight home Monday was cancelled and we were rebooked on a 7:00am flight on 9/29 with a layover in JFK. We were traveling with sick kids coming home from a funeral of a loved one and needed to be at work on Tuesday so paying extra for a flight home Monday was something we had to do. The original direct flights were considerably more expensive than the non direct flights- so I don't understand how Jetblue did absolutely NOTHING to compensate or right their mistake. We will not be booking with them in the future because they are not reliable and they showed no remorse nor did they make any attempt to make things right. The least they could have done was credit the difference in cost of flight because I know our original flights cost more than the one we were rebooked on. Once again- we will not be flying with them in the future and will advise family and friends to be aware of the risk you run when giving them your business. Do better.

The flight attendant was snarky and the flight took off very late. I know it was an issue with air traffic control and the runways in Boston, so not really anyone's fault, but very frustrating, I missed an important meeting because of rgr delay. They didn't offer headphones to watch the TV, but luckily I remembered my own and was able to enjoy watching a movie.

Terrible. We originally booked a direct flight from BOS to MCO on 9/28 at 8:00pm and it was cancelled due to unforeseen circumstances and the flight we were rebooked on was on 9/29 at 7:00am with a layover in JFK. We were traveling with sick kids so leaving at such an early hour was absolutely miserable, and on top of that we all missed work which we couldn’t afford. On top of that- we paid a fortune for our flights to be direct without a layover and the flights with layovers were cheaper so at the very minimum we should have been refunded the difference. With absolutely no explanation or sympathy from JetBlue- we will avoid using them in the future due to the fact they aren’t reliable nor do they correct their mistakes.

Experience with JetBlue was poor. We were originally suppose to fly home on a direct flight on Monday the 28th at 8:00pm and we it was canceled due to “unforeseen circumstances” and we were rebooked on a 7am flight on Tuesday the 29th with a layover in JFK. Traveling with sick kids and waking up at an ungodly hour was miserable, and not only that it caused all of us to miss work. We intentionally flew our Monday on a direct flight and the direct flight was far more than the non direct flights on any given day. There was no compensation provided let alone a reasonable explanation. When you are charging people those type of prices for domestic same coast flights- you should be at least refunding the cost difference of the flights if you are rebooking them on a cheaper flight. I will never fly JetBlue again because they are unreliable and don’t correct their mistakes.

Wasn’t very happy with our flight home due to the fact it was cancelled with absolutely no reason. It was a direct flight at 8:00pm on Monday and they rebooked us for a 7am flight on Tuesday with a layover. Traveling with sick kids, getting up that early was miserable and on top of that we all missed a day of work that we couldn’t afford to with absolutely no apology or compensation from JetBlue. The original cost of the flights were astronomical because we flew out on Monday over Tuesday and also we paid extra for the direct flight then we would have for the flight with a layover. Super disappointed Jetblue truly could have cared less. Will avoid them in the future due to the fact they aren’t reliable nor compassionate for the inconvenience these changes cost their clients.

No WiFi, no power to charge phone, confusing boarding, delays

There is a considerable amount of people that use the wheel chair pre boarding along of large groups of family / friends. This is not right should be limited only to the person in need and the airline assistant. Some of these people use overhead bins that do not belong to them. The aircraft had a non functional wifi . The service was bad.

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.

I had to buy another ticket and you haven't reimburse me for it.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Had to find alternative flights because of AA lateness and bad planning

Fliy was late missed my connection ,. I had to find altery transportation.

When we landed, there was only one gate agent to handle three planes, including retrieval of carry on luggage. I was stuck in the jet way waiting on my carry on for almost 20-30 minutes. NOT GOOD

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.

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