$129 Find Cheap Flights from Portland to Caribbean

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 5/26. 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$352
Santo Domingo
Santo Domingo1 stop$381
Montego Bay
Montego Bay2 stops$411
Oranjestad
Oranjestad2 stops$350
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$534
Simpson Bay
Simpson Bay2 stops$362
Providenciales
Providenciales1 stop$583
George Town
George Town1 stop$321
Puerto Plata
Puerto Plata2 stops$735
Punta Cana
Punta Cana1 stop$352
Santo Domingo
Santo Domingo1 stop$381
Montego Bay
Montego Bay2 stops$411
Oranjestad
Oranjestad2 stops$350
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$534
Simpson Bay
Simpson Bay2 stops$362
Providenciales
Providenciales1 stop$583
George Town
George Town1 stop$321
Puerto Plata
Puerto Plata2 stops$735

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

Tue, Oct 20 - Sun, Oct 25
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
United Airlines Logo
1:05 am - 8:19 am
SJU
-
PWM
7h 14m
1 stop
$298United Airlines
Tue, Oct 20 - Mon, Oct 26
American Airlines Logo
6:00 am - 1:35 pm
PWM
-
SJU
7h 35m
1 stop
American Airlines Logo
5:25 am - 7:16 pm
SJU
-
PWM
13h 51m
1 stop
$302American Airlines
Tue, Oct 20 - Mon, Oct 26
American Airlines Logo
2:55 pm - 11:50 pm
PWM
-
SJU
8h 55m
1 stop
American Airlines Logo
5:25 am - 6:25 pm
SJU
-
PWM
13h 00m
1 stop
$312American Airlines
Thu, May 28 - Tue, Jun 2
Delta Logo
6:00 am - 11:54 am
PWM
-
GCM
6h 54m
1 stop
Delta Logo
1:19 pm - 11:09 pm
GCM
-
PWM
8h 50m
1 stop
$321Delta
Fri, May 29 - Tue, Jun 2
Delta Logo
2:38 pm - 11:54 am
PWM
-
GCM
22h 16m
2 stops
Delta Logo
1:19 pm - 12:43 am
GCM
-
PWM
10h 24m
2 stops
$326Delta
Thu, Jul 9 - Wed, Jul 15
Delta Logo
6:00 am - 2:23 pm
PWM
-
STT
8h 23m
1 stop
Delta Logo
4:31 pm - 12:59 am
STT
-
PWM
8h 28m
1 stop
$333Delta
Tue, Sep 29 - Tue, Oct 13
Delta Logo
6:00 am - 1:49 pm
PWM
-
NAS
7h 49m
1 stop
Delta Logo
12:55 pm - 11:49 pm
NAS
-
PWM
10h 54m
1 stop
$340Delta
Wed, Oct 28 - Sat, Oct 31
United Airlines Logo
6:00 am - 12:49 pm
PWM
-
PUJ
6h 49m
1 stop
United Airlines Logo
11:56 am - 11:59 pm
PUJ
-
PWM
12h 03m
1 stop
$352United Airlines
Fri, Jun 5 - Sat, Jun 13
JetBlue Logo
2:37 pm - 12:43 pm
PWM
-
STT
22h 06m
2 stops
JetBlue Logo
2:00 pm - 12:30 pm
STT
-
PWM
22h 30m
3 stops
$585JetBlue
Fri, Jun 5 - Sat, Jun 13
JetBlue Logo
2:37 pm - 2:58 pm
PWM
-
STT
24h 21m
2 stops
JetBlue Logo
2:00 pm - 12:30 pm
STT
-
PWM
22h 30m
3 stops
$592JetBlue
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 February, when tickets cost $101 (return) on average. On the other hand, the most expensive months are December and September, when the average cost of round-trip tickets is $298 and $282 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$129
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 16% 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 4299 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

2.0 MediocreAnonymous, May 2026
MCO - MDW
Read more Southwest reviews

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

It was good overall except from Omaha to Denver when flight a was a repeatedly delayed apparently due to some issue at Denver. Communications could have been handled better. I had to board then deboard with luggage and board again

I didn’t have a seat assignment and my seat was very dirty on the flight from Frankfurt to Budapest.

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

No screens or meal options. Freezing cold. Dirty seats. Left late.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Cree was organized and pleasant. Plane had good seating but as it’s a shuttle toilets hadn’t been thoroughly cleaned (eg. bins too full)

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

There was a screen but no earphones that could use the older input so I could listen to anything.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports