$138 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 1/18. 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.
1 adult
1 adult, Economy, 0 bags

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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$464
Santo Domingo
Santo Domingo1 stop$447
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$494
Nassau
Nassau1 stop$368
Kingston
Kingston1 stop$472
Simpson Bay
Simpson Bay1 stop$507
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata1 stop$635
Punta Cana
Punta Cana1 stop$464
Santo Domingo
Santo Domingo1 stop$447
Montego Bay
Montego Bay1 stop$384
Oranjestad
Oranjestad2 stops$494
Nassau
Nassau1 stop$368
Kingston
Kingston1 stop$472
Simpson Bay
Simpson Bay1 stop$507
Providenciales
Providenciales1 stop$423
George Town
George Town1 stop$357
Puerto Plata
Puerto Plata1 stop$635

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

Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
7:26 pm - 2:55 pmPWM  Portland-STT Saint Thomas Island Cyril E King
19h 29m2 stops Philadelphia Miami
American Airlines Logo
2:01 pm - 9:36 pmSTT  Saint Thomas Island Cyril E King-PWM Portland
8h 35m1 stop Charlotte Douglas
$280American Airlines
Thu, Oct 29 - Mon, Nov 2
American Airlines Logo
4:40 pm - 12:58 pmPWM  Portland-STT Saint Thomas Island Cyril E King
20h 18m2 stops Philadelphia Miami
American Airlines Logo
3:15 pm - 10:37 amSTT  Saint Thomas Island Cyril E King-PWM Portland
20h 22m2 stops Miami Philadelphia
$280American Airlines
Sun, Jan 31 - Wed, Feb 3
United Airlines Logo
6:00 am - 2:40 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 40m1 stop Newark
United Airlines Logo
2:05 am - 8:19 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 14m1 stop Newark
$348United Airlines
Sun, Jan 31 - Mon, Feb 8
United Airlines Logo
6:00 am - 2:40 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 40m1 stop Newark
United Airlines Logo
2:05 am - 8:19 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
7h 14m1 stop Newark
$348United Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:00 am - 4:49 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
10h 49m1 stop Atlanta Hartsfield-Jackson
Delta Logo
7:30 am - 1:54 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
6h 24m1 stop New York John F Kennedy Intl
$352Delta
Thu, Oct 22 - Mon, Oct 26
Delta Logo
4:15 pm - 11:44 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
7h 29m1 stop New York John F Kennedy Intl
Delta Logo
1:15 pm - 12:10 amSJU  San Juan Luis Munoz Marin Intl-PWM Portland
10h 55m1 stop New York John F Kennedy Intl
$352Delta
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
6:41 am - 3:59 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 18m1 stop New York John F Kennedy Intl
JetBlue Logo
7:25 am - 1:45 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
6h 20m1 stop New York John F Kennedy Intl
$408JetBlue
Sat, Aug 29 - Wed, Sep 2
JetBlue Logo
6:41 am - 3:59 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 18m1 stop New York John F Kennedy Intl
JetBlue Logo
5:01 am - 1:45 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
8h 44m1 stop New York John F Kennedy Intl
$408JetBlue
Tue, Jan 19 - Tue, Jan 26
Southwest Logo
5:35 am - 3:50 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
6:15 am - 12:10 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
6h 55m1 stop Baltimore/Washington
$408Southwest
Tue, Jan 19 - Tue, Jan 26
Southwest Logo
5:35 am - 3:50 pmPWM  Portland-SJU San Juan Luis Munoz Marin Intl
9h 15m2 stops Baltimore/Washington Orlando
Southwest Logo
5:45 am - 2:40 pmSJU  San Juan Luis Munoz Marin Intl-PWM Portland
9h 55m2 stops Orlando Baltimore/Washington
$408Southwest
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 September, when tickets cost $418 (return) on average. On the other hand, the most expensive months are July and April, when the average cost of round-trip tickets is $696 and $694 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 2 weeks before departure, which saves you about 30% 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

$138
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 13% increase in price.
Flight from Portland to Saint Thomas Island

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 4217 reviews
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

10.0 ExcellentAndrew, Aug 2026
Read more Southwest reviews

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

The flight was delayed due to earlier issues at other airports. The crew was excellent & made it a good trip.

Boarding process of asking for volunteers to check bags goes against the system you had before with 2 bags checked free. This process is more of a guilt trip than a caring attitude toward the customer. In addition bag-size scrutiny has increased which also slows down the process of boarding. My wife said she will not fly on your airline again unless there is no other option.

Eveeyrime I fly they are begging for bags due to cabin overhead space. What they should so ia take the bags that are clearly too big to fit wheels first on their side. And those of us who give up the bag should really get their bags first. When boarding, nobody wants stupid jokes about how hot it is on board. Give us some cool air. Im usually sick from the heat by the time we take off.

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

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.

Although I know the Airlines cannot control the situation when there’s a ground stoppage, it would’ve been nicer if we would have had more up-to-date information clarity around the delays. Additionally, I think the delays also took a toll on the Cabin crew, particularly the lead flight attendant in first class. She was not very friendly when we boarded the plane for many of the passengers. Number one she refused to hang a garment bag in the front closet for a first class passenger, she was unwilling to dispose of an empty bottle in the trash as I was boarding (despite drinking a bottle of water herself and needing to disregard), and she was very combative with a passenger, who needed to access something from his bag that was Gate checked. Frankly, it was really unfortunate as I’ve never seen a flight attendant behave that way directly to the passengers, particularly when none of us had done anything wrong.

overall the crew onboarding and providing service during our flight was great; they were friendly and helpful. I said ok to the entertainment because there was none, but the crew explained why which was very helpful. I am a diabetic and the type of snacks are not diabetic friendly (full of carbs and sugar). However, I am always prepared because I know the catering is for the larger population.

While it wasn't the crew's fault, it was a frustrating flight. We sat on the runway for 2+ hours. Both of the flight attendants were excellent and did a great job checking on the passengers. The pilot did keep us informed about the wait. I appreciate the crew apologizing for LaGuardia airport's backup.

the flight got cancelled - few hours before the departure time - no time to change

This a short easy flight. No food or drink but that was not an issue since we were only in the air for 35 minutes.

The meal tray was not usable it was completely uneven

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The ac must have died, it was way to hot on this flight. Boarding g was chaotic. The flight was delayed for boarding. Not a great experience.

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

Like the fact that the boarding was expedited. But the delay and chaos around the onboarding was not appreciated.

Flight was 2.5 late. Maybe not United’s fault but late none the less. We were late as well on the first leg. WiFi quit working with an hour left.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

The flight to America was freezing. The overnight flight back to the UK was boiling hot and the cabin stank of toilet or occasionally perfume, even though I was several rows back from either bathroom. Food was tiny portions. Two small pieces of tough and dry beef in random gravy with pretend mashed potato raking up most of it. Very little veg. Salad was ok. Wooden cutlery broke within minutes of using. Lots of old films for entertainment. Some new ones. Generally a bit rubbish.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

Staff and flight attendants were very polite. Flight was smooth. My seat on the plane was a bit broken so it would not stay in upright position but it was fine for the most part.

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.

Did not know that they didn’t have screens for entertainment. I didn’t have headphones so I couldn’t watch anything on my phone.

Delayed couple hours due to airplane maintenance issues, we boarded and then asked to unboard, but cmon!! Can they do the whole maintenance prior to boarding?

No food. I paid over $1.000 for my ticket for nuts and espresso beans.

I was so hungry. No meals. Staff very nice. Seat arms armed too tight and didn’t go up. I was scheduled for First class, but was put on Standby, even though I made my reservation a while ago. Thank you.

Boarding was horrendous! Took absolutely forever… and the delay from the broken coffee pot was really kind of ridiculous

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.

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

When I booked, I included my checked luggage and when the bill was sent there was no record of this. Its was costly since I am from Trinidad amd Tobago. Exchange rate over seven dollars to one US dollar.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports