$353 Find Cheap Flights from Caribbean Islands to Portland

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 11/24. 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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Cheap Flights from Caribbean Islands to Portland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to Portland 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 Caribbean Islands to Portland

Mon, Nov 24 - Fri, Nov 28
American Airlines Logo
6:30 am - 2:54 pmSJU-PWM
9h 24m1 stop
American Airlines Logo
4:18 pm - 11:31 pmPWM-SJU
6h 13m1 stop
$353American Airlines
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Mon, Nov 24 - Fri, Nov 28
American Airlines Logo
6:30 am - 4:28 pmSJU-PWM
10h 58m2 stops
American Airlines Logo
4:18 pm - 11:31 pmPWM-SJU
6h 13m1 stop
$393American Airlines
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Wed, Oct 15 - Sun, Oct 19
Delta Logo
7:00 am - 1:52 pmSJU-PWM
6h 52m1 stop
Delta Logo
5:40 am - 4:18 pmPWM-SJU
10h 38m1 stop
$425Delta
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Fri, Aug 15 - Sat, Aug 23
Delta Logo
1:34 pm - 12:48 amSJU-PWM
11h 14m1 stop
Delta Logo
6:31 am - 4:27 pmPWM-SJU
9h 56m1 stop
$451Delta
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Tue, Oct 14 - Sun, Oct 19
United Airlines Logo
1:05 am - 9:11 amSJU-PWM
8h 06m1 stop
United Airlines Logo
6:14 am - 2:44 pmPWM-SJU
8h 30m1 stop
$511United Airlines
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Wed, Jul 16 - Sun, Jul 20
United Airlines Logo
1:10 am - 2:23 pmSJU-PWM
13h 13m2 stops
United Airlines Logo
6:00 am - 1:45 pmPWM-SJU
7h 45m1 stop
$570United Airlines
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Mon, Aug 11 - Thu, Aug 14
Southwest Logo
5:50 am - 2:45 pmSJU-PWM
8h 55m1 stop
Southwest Logo
10:35 am - 8:45 pmPWM-SJU
10h 10m2 stops
$600Southwest
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Mon, Aug 11 - Thu, Aug 14
Southwest Logo
5:50 am - 2:45 pmSJU-PWM
8h 55m1 stop
Southwest Logo
12:35 pm - 11:30 pmPWM-SJU
10h 55m1 stop
$609Southwest
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Thu, Aug 14 - Sat, Aug 23
JetBlue Logo
3:25 am - 1:23 pmSJU-PWM
9h 58m1 stop
JetBlue Logo
2:20 pm - 12:54 amPWM-SJU
10h 34m1 stop
$634JetBlue
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Sun, Aug 10 - Thu, Aug 14
JetBlue Logo
3:25 am - 1:23 pmSJU-PWM
9h 58m1 stop
JetBlue Logo
2:20 pm - 12:54 amPWM-SJU
10h 34m1 stop
$796JetBlue
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Good to know

Low seasonFebruary
High seasonDecember
Cheapest flight$353
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 44% increase in price.
Flight from San Juan to Portland

FAQs for booking flights from Caribbean Islands to Portland

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

    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 Caribbean Islands to Portland.

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

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

    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 to Portland with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to Portland?

    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 to Portland from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top 4 airlines serving from Caribbean Islands to Portland

 
Need help choosing which airline to fly with from Caribbean Islands to Portland? 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
DeltaOverall score based on 7963 reviews
8.5Crew
8.2Boarding
7.9Comfort
7.9Entertainment
7.3Food
Airline reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

4.0 OkayKoonj, Jun 2025MSP - AUS
Read more Delta reviews

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

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.

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.

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.

United airlines, mediocre at best. No issues , nothing great . Worked for me

Efficient, calm when things were delayed and kept us regularly informed of what was happening.

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.

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.

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!

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

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

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. 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.

Great flight. Departed early, arrived early. However they were out of meals for sale. Also, we arrived early and the gate was not available so we sat on the taxiway for quite a while (not JetBlue’s fault).

The gate and ground staff were excellent, friendly, went out of their way to acknowledge my Mosaic status. The plane was an older Airbus, so the seats were a little worn. The in flight attendant was not very nice, and seemed to be annoyed to be at work or be on this flight. Flight was fast and we landed early and pilots kept us informed.

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.

The inflight system with their wifi is a hot mess and doesn't work. Separately they do, but when you try to do theoretically simple things like pair a device for control it all falls apart

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

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

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.

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