$135 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$425
Montego Bay
Montego Bay2 stops$404
Oranjestad
Oranjestad1 stop$340
Nassau
Nassau1 stop$326
Kingston
Kingston2 stops$492
Simpson Bay
Simpson Bay2 stops$474
Providenciales
Providenciales2 stops$431
George Town
George Town2 stops$382
Puerto Plata
Puerto Plata2 stops$597
Punta Cana
Punta Cana2 stops$425
Montego Bay
Montego Bay2 stops$404
Oranjestad
Oranjestad1 stop$340
Nassau
Nassau1 stop$326
Kingston
Kingston2 stops$492
Simpson Bay
Simpson Bay2 stops$474
Providenciales
Providenciales2 stops$431
George Town
George Town2 stops$382
Puerto Plata
Puerto Plata2 stops$597
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 $442 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $717 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 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low season

September

Cheapest flight

$135
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Portland to Oranjestad

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 4200 reviews
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
Airline reviews

Delayed and once landed waited very long for the luggage

6.0 GoodIngeborg, Sep 2026
Read more Southwest reviews

Delayed and once landed waited very long for the luggage

Nice managed … it was a smaller plane, so the seating wasn’t as comfortable.

The Southwest airline was ok. A big thank you to Kayak team (David), who worked with me on Sunday afternoon to rebook my travel from Burbank, CA, to CVG. My original flight on Sunday was delayed, so I had to cancel Sunday flight and rebook my travel to Monday. Could not have done it without help from David from Kayak team. Ante Soda GE Aerospace

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

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.

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

Delta exceeded my expectations! I am beyond satisfied. Thank you!

Flight was on time! That's the most important thing for me.

Delayed flight. Dirty seats, dirty seat belts with food stuck on it from previous passengers maybe. No one cleaned the seats or flight.

The flight was delayed and knowing I was going to miss my connection, nothing was done proactively to try and get me rebooked. It was an act of congress to do so. This is not on the crew, but on the experience itself

No headphones, forced to sit in another seat that I did not book, had to check my carry on when I boarded the plane I saw backpacks and other non carry on items stuffed in the carry on holder! Horrible experience Wi-Fi did not work either

Sat in the tarmac at O’Hare for 65 minutes. This is a regular occurrence for delta at O’Hare

Delta is getting worst by the minute. Where this was at one point my only go to airline, it has become like a budget airline

All was fine. Small plane so no food or entertainment.

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

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

WiFi was slow as compared to trip down. Maybe because it was a night flight and more people were using it?

Excellent except for the 2 screaming kids who wouldn’t stop crying and screaming for the entire flight but what are you going to do? The flight was early- good experience

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

It was partially ok .. not anything like from Orlando to Houston... first the flight attendant was not so nice and insisted on have a small backpack down when really was not to put in danger anyone, also the beverages they were not so good... not big chance to select other tea.. the seat was partially ok could not have those flips to hold your head.. and finally when it land off in Guadalajara, it was raining and the flight was going to the main area then go back and drop us out of nowhere with the rain.

Airplane is not very clean, food quality and taste was not good. Lufthansa used to be good but nowadays went down. Overall experience is just okay, wouldn't fly again, prefer Turkish airlines.

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.

My flights were all delayed , mostly due to technical issues with AA aircrafts. I had to rebook my trip 4 times . I lost my whole day and finally arrived in LAX around midnight. This was a very bad experience with American airlines , I will always try to avoid flying with them

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

Delayed and WIFI was not working for most of flight.

The big challenge here was that the inbound flight was delayed, THEN, the aircraft was deemed in need of service, so we had to deplane after being a few minutes away from departure, THEN we had to switch terminals, where another plane in our gate had maintenance issues so we had to change gates again. I am a regular flyer (not on American) so I understand these things happen. The crew was great. The pilot in particular was gracious and understanding and stayed with the passengers the whole time to answer questions and give updates - that was impressive. But the flight was massively delayed as a result, and today I really wanted to be home in time. Sigh The flight was otherwise great.

I am Plstinum Pro snd was standby on earlier flight. They gave seats to people that asked rather than follow standby order. When realized what was happening was too late to get on as no seats left. My scheduled flight was late. Then filled the seat beside me Ruth rude person that they had to move from her original seat

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.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Fabulous! This was the first time we've flown with JetBlue and the entire experience was flawless!

First time flying JetBlue and my perception changed. Love it.

Poor, had a 5+ hours delay. Kept sitting in the aircraft with three kids. It was terrible

The plane was filthy and worn - the seat pockets were stuffed with tattered food and torn pamphlets. The cleaning crew that came on as we were deboarding were grabbing handfulls of trash and perfunctorily wiping down tables with dishrags. It's been a while since I flew Jetblue and it used to be a great experience. After this flight I will avoid flying Jetblue again if there is any alternative.

I have flown Jet Blue many times between JFK and SFO. I appreciate how clean the planes are, the ability to select my onboard entertainment and the flight crews have always been amazing! Unfortunately, my trip from SFO to JFK on August 23 was unusual. I arrived early at SFO for the 12:00 noon scheduled boarding. The flight was supposed to take off at 12:45pm but after sitting for a while, the plane had to return to the gate to have a generator inspected. After deplaning and then reboarding, we eventually took off around 3:30 pm. It was explained to the passengers that because the plane was using a backup generator, additional fuel was needed and the flight would take longer than originally scheduled. We were originally supposed to arrive at JFK at 9:32 pm but instead, arrived at midnight. Unfortunately, I was exhausted for the funeral I attended the next morning. As a passenger, I have always expected that the plane will be in good mechanical order and that all parts will function as expected. I'm not entirely certain that if I fly Jet Blue in the future, that I will have the same level of confidence that I had become accustomed to. Thanks for the opportunity to provide this feedback. Kathy Nigro

More options for your flight to Caribbean

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