$121 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 8/26. 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

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Best Caribbean Flight Deals from Portland

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$413
Santo Domingo
Santo Domingo1 stop$467
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$386
Nassau
Nassau1 stop$349
Simpson Bay
Simpson Bay2 stops$567
George Town
George Town2 stops$487
Punta Cana
Punta Cana1 stop$413
Santo Domingo
Santo Domingo1 stop$467
Montego Bay
Montego Bay1 stop$371
Oranjestad
Oranjestad1 stop$386
Nassau
Nassau1 stop$349
Simpson Bay
Simpson Bay2 stops$567
George Town
George Town2 stops$487

Cheap Flights from Portland to Caribbean

 
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

Sat, Oct 4 - Sun, Oct 12
Frontier Logo
6:12 pm - 7:59 amPWM-SJU
13h 47m1 stop
Frontier Logo
9:07 am - 11:05 amSJU-PWM
25h 58m1 stop
$203Frontier
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Sat, Oct 4 - Sun, Oct 12
Frontier Logo
6:12 pm - 7:59 amPWM-SJU
13h 47m1 stop
Frontier Logo
3:40 am - 11:05 amSJU-PWM
7h 25m1 stop
$221Frontier
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Tue, Aug 19 - Sat, Aug 23
Delta Logo
2:36 pm - 11:51 pmPWM-SJU
9h 15m1 stop
Delta Logo
12:50 pm - 12:03 amSJU-PWM
11h 13m1 stop
$275Delta
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Fri, Jul 4 - Wed, Jul 9
United Airlines Logo
3:50 pm - 12:02 amPWM-SJU
8h 12m1 stop
United Airlines Logo
1:10 am - 2:24 pmSJU-PWM
13h 14m2 stops
$341United Airlines
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Tue, Oct 21 - Tue, Oct 28
Delta Logo
5:40 am - 11:58 amPWM-NAS
6h 18m1 stop
Delta Logo
1:25 pm - 11:31 pmNAS-PWM
10h 06m1 stop
$349Delta
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Tue, Sep 9 - Thu, Sep 25
American Airlines Logo
6:00 am - 1:38 pmPWM-MBJ
8h 38m2 stops
American Airlines Logo
4:09 pm - 11:47 amMBJ-PWM
18h 38m2 stops
$375American Airlines
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Fri, Jul 4 - Wed, Jul 9
United Airlines Logo
2:08 pm - 12:02 amPWM-SJU
9h 54m2 stops
United Airlines Logo
1:10 am - 2:24 pmSJU-PWM
13h 14m2 stops
$381United Airlines
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Tue, Sep 9 - Thu, Sep 25
American Airlines Logo
6:00 am - 1:38 pmPWM-MBJ
8h 38m2 stops
American Airlines Logo
4:09 pm - 4:17 pmMBJ-PWM
23h 08m1 stop
$383American Airlines
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Tue, Jul 15 - Sat, Jul 19
JetBlue Logo
2:19 pm - 11:34 pmPWM-SJU
9h 15m1 stop
JetBlue Logo
6:00 pm - 12:17 amSJU-PWM
6h 17m1 stop
$387JetBlue
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Wed, Jul 9 - Sat, Jul 12
JetBlue Logo
2:19 pm - 11:34 pmPWM-SJU
9h 15m1 stop
JetBlue Logo
3:05 am - 1:23 pmSJU-PWM
10h 18m1 stop
$397JetBlue
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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 $275 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $683 and $633 respectively.

What’s the cheapest day of the week to fly from Portland to Caribbean?

The average price of all round-trip flights from Portland to Caribbean clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Caribbean on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Portland to Caribbean. For your return ticket, we recommend flying on a Thursday and avoiding Tuesdays for the best deals.

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. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.


Good to know

Low seasonJuly
High seasonApril
Cheapest flight$121
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 27% increase in price.
Flight from Portland to Nassau

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $302 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $557.

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 4287 reviews
8.6Crew
7.1Food
8.0Comfort
7.6Entertainment
8.2Boarding
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Flight was delayed long enough that I was misding my connecting flight. The agents could not get me on a comparable flight, nor could they get me s Main Cabin seat I had paid for, nor could they get me on a comparable connecting flight. The gate agent would not issue meal vouchers, even though I was delayed over six hours! I had to spend over an hour and 15 minutes with customer service on the phone to See if they could get me on a better flight and get a meal voucher. Customer service was not helpful enough in trying to find alternate flights and it Ended up taking me 24 hours for a 12 hour trip!! Delta does not provide upgrades NOR will they even give you a pass for a few hours to their lounge. They claim that they do not issue daily passes to their lounge anymore. I call BS since this would be no extra cost to them to provide excellent customer service and give you a few hours to relax in comfort when you’re sitting in a crowded airport and your flight has been screwed up for that many hours.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

Flight was delayed several 3 hours - no reason was given and no communication what so ever.

No overhead baggage room even though I was seated in row 2. Consequently had to check in my carry on bag. Baggage carousel was jammed. Took 45 min to get my bag.

Excellent from start to finish. All staff members were amazing!

Excellent. Although they used to greet me as a mosaic member and provide a free drink, early boarding helps me to keep coming back to JetBlue.

Cancelled flight with no specific instructions to get a boarding pass for another flight. The whole flight of people were in line for an hour because there was only 1 person to help at the desk. This was unusual for JetBlue.

It was too hot in the cabin. The AC did not help.

Except for the 28 minute delay leaving and the earlier reschedule to a later takeoff time the flight was good.

Loved the leg room and tvs screens on the seats and free WiFi. Wish the price was lower and could save by rebooking

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

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

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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