$187 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 11/13. 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 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 - 9:37 pmSJU-PWM
14h 17m1 stop
American Airlines Logo
5:17 pm - 10:09 amPWM-SJU
15h 52m2 stops
$378American Airlines
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
12:45 pm - 11:49 pmSJU-PWM
12h 04m2 stops
American Airlines Logo
6:28 pm - 6:06 pmPWM-SJU
22h 38m2 stops
$382American 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
6:00 am - 3:57 pmPWM-SJU
8h 57m1 stop
$434American Airlines
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
8:19 am - 11:49 pmSJU-PWM
16h 30m2 stops
American Airlines Logo
5:35 am - 9:26 pmPWM-SJU
14h 51m2 stops
$469American Airlines
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Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
8:10 am - 2:23 pmSJU-PWM
7h 13m1 stop
United Airlines Logo
3:05 pm - 12:36 amPWM-SJU
8h 31m1 stop
$502United Airlines
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Wed, Feb 18 - Sat, Feb 21
Delta Logo
7:00 am - 1:45 pmSJU-PWM
7h 45m1 stop
Delta Logo
2:35 pm - 11:58 pmPWM-SJU
8h 23m1 stop
$534Delta
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
3:54 pm - 10:29 pmSJU-PWM
7h 35m1 stop
American Airlines Logo
5:35 am - 9:26 pmPWM-SJU
14h 51m2 stops
$550American Airlines
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Wed, Feb 18 - Sat, Feb 21
United Airlines Logo
8:10 am - 2:23 pmSJU-PWM
7h 13m1 stop
United Airlines Logo
3:05 pm - 12:36 amPWM-SJU
8h 31m1 stop
$553United 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
$773United 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 - 9:00 pmPWM-SJU
14h 00m2 stops
$871United Airlines
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Everything you should know

Cheapest round-trip
$378
American Airlines
Fri 12/12Mon 12/15
SJU - PWM • 1 stop
Cheapest one-way
$141
Typical prices: $215-$246
Delta
Thu 11/13
SJU - PWM • 1 stop
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Portland!
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$141
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 49% increase in price.
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 8004 reviews
7.9Entertainment
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
Airline reviews

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

10.0 ExcellentMAYRA, Nov 2025JFK - MIA
Read more Delta reviews

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.

Non stop on long haul is the way to go. Great experience

Seats comfortable, service and food very mediocre, staff not very attentive, worse than many other our flights with Delta.

Overall good experience; however, there was one flight attendant who was rather rough compared to everyone else. Everything else was good: entertainment, food. Delta keeps on delivering! Thank you!

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

Very disappointed with food service. They ran out of entree selections- so for the last 10 rows only option was lentil stew. Not a fan. Then the morning service (pizza twist) was lukewarm at best- I exited my 12 hour flight having eaten a roll and dessert. They knew it was a full flight.

Premium Plus is a really good idea for longer flights

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

Not enough veg food available for passengers. I actually did not get the veg food and was told it was over, and I starved the entire flight duration.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Flight left on time. Boarding was easy. Arrived to EWR 30 mins early. Luggage was deplaned in good time. Overall a very good experience.

Flight from Rome to SFO was excellent compared To our flight to Europe from SFO. The food was much tastier. You can see how UNITED is skimping, though. Instead of getting something mid flight you had to ask for it. It was not automatically served. There was a cookie at the end of the arrival meal, for example that tasted like it just came out of a box. They used to serve a little container of nuts, now … a tiny container of nuts, mixed with pretzels. This was business class that you really have to pay for! But this is minor complaints compared to the overall. My major complaint is the position of the even numbered seats by the windows. You have to turn around to see your window & the positioning as some other controls are harder to get at. This is compared to the odd number seat that are perfectly aligned.

The person I bought the ticket for didn’t make the flight.

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

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Nice comfortable flight from Barcelona back to the states. The premium economy offers the extra room we need for my husband. The food was good and our flight attendants were excellent.

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
Jackson
Freeport
Bartlett
Oxford
Windham
Intervale
Tamworth
Falmouth
Durham
Waterford

Everything you need to know for your flight to Portland

Information on the airport you'll fly into in Portland

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