$110 Find Cheap Flights from Portland to Caribbean Islands - Compare and Save

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Cheap Flights from Portland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$350
Montego Bay
Montego Bay2 stops$358
Oranjestad
Oranjestad1 stop$346
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$520
Simpson Bay
Simpson Bay1 stop$366
Providenciales
Providenciales2 stops$426
George Town
George Town2 stops$333
Puerto Plata
Puerto Plata2 stops$597
Punta Cana
Punta Cana1 stop$350
Montego Bay
Montego Bay2 stops$358
Oranjestad
Oranjestad1 stop$346
Nassau
Nassau1 stop$306
Kingston
Kingston2 stops$520
Simpson Bay
Simpson Bay1 stop$366
Providenciales
Providenciales2 stops$426
George Town
George Town2 stops$333
Puerto Plata
Puerto Plata2 stops$597
Booking Insights

KAYAK's insights & trends for Portland to Caribbean Islands flights

Get data-powered insights and trends into flights from Portland to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Portland to Caribbean Islands?

No, with an average price for the route of $398, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Portland to Caribbean Islands?

The cheapest month for flights from Portland to Caribbean Islands is August, when tickets cost $460 (return) on average. On the other hand, the most expensive months are April and July, when the average cost of round-trip tickets is $709 and $704 respectively.

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

To get a below average price on the flight from Portland to Caribbean Islands, 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 24 weeks before departure.

Good to know

Low season

September

Cheapest flight

$110
Best time to beat the crowds but there is an average 30% increase in price.
Most popular time to fly with an average 16% increase in price.
Flight from Portland to Saint Thomas Island

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Portland to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Portland to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Portland to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
Need help choosing which airline to fly with from Portland to Caribbean Islands? 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 4189 reviews
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
Airline reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

6.0 GoodAnonymous, Sep 2026
Read more Southwest reviews

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Terrible delay today. also, waited 90 minutes for baggage to unload in Seattle earlier in the week.

Like new plane. Great crew. Comfortable. Clean. On time. Happy employees. Good organization and control of passengers.

Flights delays were communicated timely and helpfully, but there was a significant delay without any real effort to make up for that. Also, the in-flight WiFi was very spotty. That said, this was my first time with Southwest and I was quite happy with the service and staff otherwise.

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.

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.

THI IS THE 3RD CONSECUTIVE FLIGHT FROM ORD TO MSP THAT HAS BEEN DELAYED 2+ HOURS. CRAZY

Sat in the plane at the gate in SLC for 2+ hours before take off, getting me home nearly 3 hours later than planned.

I was impressed with how quickly the baggage transfers were made.

The Airline Attendant found us in flight and moved us to seats in the front of economy due to the short time we would have to make our connecting flight. We really appreciated it.

For some reason, there was very little volume on the cabin announcements. You could not hear what the pilot or crew were saying.

Carmen was an absolute delight on the flight staff! Everyone was lovely and made it a very pleasant flight.

Flight was delayed at airport with large backlog and WiFi was spotty

I don’t like mushrooms and that’s all they had with pasta

I Love Delta but one of the flight crew training in courtesy snd hospitality.

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

awesome team work seen since on board till off plane in my destination. thanks you so much.

Job well done, being treated for good and helping a lot . thanks you so much till will meet against.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

They did not have free WIFI and I was not okay with that!

Food was very bad Crew was not so welcoming. Chairs was so uncomfortable

Flight was on time, clean, etc. Despite connecting to your wi fi I was unable to use your app to watch entertainment.

I initially boarded in a very comfortable and large plane and was told there was a mechanical issue with a waste receptacle. We sat on the plan for a good few hours, then were told we can deplane and that we would take off shortly. Delays continued and four hours later my flight was cancelled, and I had to quickly rebook another. The flight I rebooked was also delayed, and I when we boarded, I wound up on a small plane in a middle seat for the 6-hour journey and it was extremely uncomfortable. No issues with the staff in any way, just the overall experience of the delays, cancellations, and downgrade in comfort on such a long flight. It is significantly impactful on how you feel post travel and I was exhausted and sore from the experience.

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.

Had to pay for WiFi, delayed start, and sat on the runway forever.

As with most flights these days it was delayed by about 30 min.

The airline company should manage their crew for the plane on better schedule so people don’t have to wait in the plane. And this flight that I had had no snacks offered, and if you would like a water, you had to come see somebody and ask for. If airline would let people know that they are no longer providing or offering any food. At least people could bring their own if they wish.

The flight was delay roughly 90 minutes. Once we arrived at O'Hare, we sat on the tarmac for another 90 minutes. I understand that O'Hare is under construction however they need to figure out a solution as every incoming flight I have been on has been delayed coming to a gate.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

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.

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

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

More options for your flight to Caribbean Islands

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