$108 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 11/9. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Portland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$355
Santo Domingo
Santo Domingo2 stops$381
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$367
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$535
Simpson Bay
Simpson Bay2 stops$362
Providenciales
Providenciales1 stop$587
George Town
George Town2 stops$445
Puerto Plata
Puerto Plata2 stops$735
Punta Cana
Punta Cana2 stops$355
Santo Domingo
Santo Domingo2 stops$381
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad2 stops$367
Nassau
Nassau1 stop$340
Kingston
Kingston2 stops$535
Simpson Bay
Simpson Bay2 stops$362
Providenciales
Providenciales1 stop$587
George Town
George Town2 stops$445
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

Fri, Sep 25 - Sun, Sep 27
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
United Airlines Logo
1:00 am - 10:04 am
SJU
-
PWM
9h 04m
2 stops
$298United Airlines
Sat, Sep 19 - Sat, Sep 26
Delta Logo
6:02 am - 12:13 pm
PWM
-
SJU
6h 11m
1 stop
Delta Logo
7:00 am - 1:54 pm
SJU
-
PWM
6h 54m
1 stop
$302Delta
Wed, Sep 16 - Wed, Sep 23
American Airlines Logo
5:30 am - 3:40 pm
PWM
-
SJU
10h 10m
2 stops
American Airlines Logo
6:27 am - 11:59 pm
SJU
-
PWM
17h 32m
2 stops
$307American Airlines
Fri, Sep 25 - Sun, Sep 27
United Airlines Logo
6:00 am - 8:38 pm
PWM
-
SJU
14h 38m
2 stops
United Airlines Logo
1:00 am - 10:04 am
SJU
-
PWM
9h 04m
2 stops
$316United Airlines
Fri, Oct 16 - Fri, Oct 23
American Airlines Logo
6:50 pm - 2:35 pm
PWM
-
STT
19h 45m
2 stops
American Airlines Logo
1:50 pm - 12:17 pm
STT
-
PWM
22h 27m
2 stops
$320American Airlines
Wed, Sep 30 - Tue, Oct 6
American Airlines Logo
7:32 am - 12:51 pm
PWM
-
STT
29h 19m
2 stops
American Airlines Logo
5:40 pm - 11:54 am
STT
-
PWM
18h 14m
2 stops
$325American Airlines
Mon, Nov 16 - Sat, Nov 21
Delta Logo
6:00 am - 1:30 pm
PWM
-
NAS
7h 30m
1 stop
Delta Logo
2:55 pm - 10:23 pm
NAS
-
PWM
7h 28m
1 stop
$340Delta
Tue, Oct 20 - Mon, Oct 26
American Airlines Logo
1:05 pm - 11:50 pm
PWM
-
SJU
10h 45m
2 stops
American Airlines Logo
5:25 am - 6:25 pm
SJU
-
PWM
13h 00m
1 stop
$342American Airlines
Fri, Jun 26 - Thu, Jul 2
JetBlue Logo
6:25 am - 6:04 pm
PWM
-
SDQ
11h 39m
1 stop
JetBlue Logo
2:41 pm - 11:05 pm
SDQ
-
PWM
8h 24m
1 stop
$502JetBlue
Fri, Jun 26 - Thu, Jul 2
JetBlue Logo
6:25 am - 6:04 pm
PWM
-
SDQ
11h 39m
1 stop
JetBlue Logo
2:41 pm - 11:05 pm
SDQ
-
PWM
8h 24m
1 stop
$547JetBlue
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 22 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$108
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 16% increase in price.
Flight from Portland to George Town

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 4265 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

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.

The crew were efficient. The pilots seemed professional. It was a bit chilly in our seats. The sheet provided weren’t very helpful.

Weather caused a long delay, but the efficiency and updates from the pilot were helpful. We were able to make our connection fortunately.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

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.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

Boarding was easy. Provided drinks and snacks. Good aircraft and staff

Not very happy because of the long delaying which causes our luggages were not on the connection flight and nearly missed our connection flight.

JetBlue was good. Kayak offered us a deal if we bundled the rental car. This was a complete scam. Kayak said the total was $222... but when we went to pick up the car the agent at Rent a wreck said that we had to pay "fees and taxes" for a grand total of $750. I would recommend not using kayak or rent a wreck. They are both complicit in this scam. JetBlue worked out well.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports