$118 Find Cheap Flights from Caribbean to Portland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Portland departing on 12/5. 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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Cheapest round-trip
$298
American Airlines
Fri 12/12Mon 12/15
SJU - PWM • 2 stops
Cheapest one-way
$118
Typical prices: $195-$246
American Airlines
Fri 12/5
SJU - PWM • 2 stops
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Flight Deals

Cheap Flights from Caribbean to Portland

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

Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
8:20 am - 11:37 pmSJU-PWM
16h 17m2 stops
American Airlines Logo
5:34 am - 10:09 pmPWM-SJU
15h 35m2 stops
$298American Airlines
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Tue, Dec 23 - Mon, Jan 12
Multiple Airlines Logo
4:19 pm - 11:18 amSJU-PWM
43h 59m2 stops
Multiple Airlines Logo
9:47 am - 11:32 pmPWM-SJU
12h 45m1 stop
$353Multiple Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
8:20 am - 9:37 pmSJU-PWM
14h 17m1 stop
American Airlines Logo
5:34 am - 10:09 pmPWM-SJU
15h 35m2 stops
$361American Airlines
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Fri, Nov 14 - Sun, Nov 16
United Airlines Logo
5:50 pm - 11:59 pmSJU-PWM
7h 09m1 stop
United Airlines Logo
5:30 am - 1:17 pmPWM-SJU
6h 47m1 stop
$363United Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
11:00 am - 11:37 pmSJU-PWM
13h 37m2 stops
American Airlines Logo
6:00 am - 11:52 pmPWM-SJU
16h 52m1 stop
$378American Airlines
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Fri, Dec 12 - Mon, Dec 15
Delta Logo
6:35 pm - 11:59 pmSJU-PWM
6h 24m1 stop
Delta Logo
2:34 pm - 11:59 pmPWM-SJU
8h 25m1 stop
$380Delta
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Tue, Dec 23 - Mon, Jan 12
American Airlines Logo
5:24 am - 4:39 pmSJU-PWM
12h 15m2 stops
American Airlines Logo
5:20 am - 8:50 pmPWM-SJU
14h 30m2 stops
$385American Airlines
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Fri, Nov 14 - Sun, Nov 16
Southwest Logo
6:40 am - 4:50 pmSJU-PWM
11h 10m2 stops
Southwest Logo
11:50 am - 10:20 pmPWM-SJU
9h 30m2 stops
$401Southwest
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
8:20 am - 9:37 pmSJU-PWM
14h 17m1 stop
American Airlines Logo
3:55 pm - 11:52 pmPWM-SJU
6h 57m1 stop
$441American Airlines
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Thu, Dec 11 - Mon, Dec 15
United Airlines Logo
2:05 am - 9:10 amSJU-PWM
8h 05m1 stop
United Airlines Logo
6:00 am - 2:40 pmPWM-SJU
7h 40m1 stop
$557United Airlines
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Good to know

Cheapest flight$118
Flight from San Juan to Portland

FAQs for booking flights from Caribbean to Portland

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Portland from 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 Caribbean 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean to Portland

 
Need help choosing which airline to fly with from Caribbean 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.
7.9
DeltaOverall score based on 8008 reviews
7.9Comfort
7.9Entertainment
8.5Crew
7.3Food
8.1Boarding
Airline reviews

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

10.0 ExcellentDuane, Nov 2025PBI - ATL
Read more Delta reviews

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

the over had ligth did not work'd for the all way

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

DELTA does a terrific job making sure you are well taken care of during the flight, gives you assurance before the flight through numerous email notifications about your upcoming flight & lastly good follow up after the flight making sure your needs were mat. It has been, is & will continue to be my carrier of choice in all my future travels. Good Job DELTA

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Great crew, excellent landing, good food. Over all great experience. Thank you!

Older aircraft, no meal, only food was for purchase. Not impressed United.

United needs to step up their game. Delayed flight leaving Seattle, San Francisco. Older aircraft, not very comfortable.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

The flight attendants were very rude, beyond comprehension. I took a business class from London to SFO for the first time on United. When I asked for a second piece of bread during dinner, the serving attendant threw a 3rd bread on my plate and said, “here. You can have this one too”! I couldn’t believe the rudeness of the attendant. Most all attendants were very rude, unhelpful, sing the food was absolutely disgusting. Never fly United internationally in business class. My flight back to SFO was a nightmare!!

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

I have a gluten allergy so did have any food

I have a gluten allergy so didn't have any food

Loved the crew . Absolutely no complaints. Except for luggage lost

Everything was good The connects, with no blame to crew. Or pilots. I understand they are short staffed. Everything went well for me. I'll be using you guys again in May if not sooner.

this plane was really old, had exit row seats and tray was in arm of seat so super uncomfortable to use. another seat they could t even use the tray it was broke. seat i. front of me had duct tape on it cause seat was ripped open... this plane should either be updated or retired.

Baggage handling poor. Second time this has happened. My bag went to San Francisco instead of Fiji. No apology. Luckily Nadi airport staff are fantastic. My bag arrived in Fiji the next day.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

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