$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 2/28. 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 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, Nov 7 - Mon, Nov 10
American Airlines Logo
3:05 pm - 9:35 pmSJU-PWM
7h 30m1 stop
American Airlines Logo
6:37 pm - 12:05 pmPWM-SJU
16h 28m2 stops
$239American Airlines
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Wed, Nov 5 - Sun, Nov 9
Southwest Logo
4:40 pm - 10:15 pmSJU-PWM
6h 35m1 stop
Southwest Logo
5:25 pm - 1:25 amPWM-SJU
7h 00m1 stop
$292Southwest
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Wed, Feb 18 - Sat, Feb 21
American Airlines Logo
5:41 am - 10:32 pmSJU-PWM
17h 51m2 stops
American Airlines Logo
5:15 pm - 1:35 pmPWM-SJU
19h 20m2 stops
$295American Airlines
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Wed, Nov 5 - Sun, Nov 9
American Airlines Logo
11:13 am - 11:59 pmSJU-PWM
13h 46m2 stops
American Airlines Logo
6:00 am - 11:52 pmPWM-SJU
16h 52m1 stop
$298American Airlines
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Fri, Dec 12 - Mon, Dec 15
American Airlines Logo
6:25 am - 12:11 pmSJU-PWM
6h 46m1 stop
American Airlines Logo
5:17 pm - 10:09 amPWM-SJU
15h 52m2 stops
$361American Airlines
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Wed, Feb 18 - Sat, Feb 21
JetBlue Logo
6:00 am - 2:26 pmSJU-PWM
9h 26m1 stop
JetBlue Logo
3:25 pm - 12:50 amPWM-SJU
8h 25m1 stop
$444JetBlue
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Wed, Feb 18 - Sat, Feb 21
JetBlue Logo
6:00 am - 2:26 pmSJU-PWM
9h 26m1 stop
JetBlue Logo
3:25 pm - 12:50 amPWM-SJU
8h 25m1 stop
$457JetBlue
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Tue, Nov 4 - Sun, Nov 9
United Airlines Logo
2:05 am - 9:19 amSJU-PWM
8h 14m1 stop
United Airlines Logo
6:00 am - 2:40 pmPWM-SJU
7h 40m1 stop
$462United 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
6:03 am - 5:28 pmPWM-SJU
10h 25m1 stop
$470Delta
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Tue, Nov 4 - Sun, Nov 9
United Airlines Logo
2:05 am - 2:12 pmSJU-PWM
13h 07m2 stops
United Airlines Logo
7:22 pm - 4:36 pmPWM-SJU
20h 14m2 stops
$515United Airlines
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Everything you should know

Cheapest round-trip
$239
Typical prices: $310-$362
American Airlines
Fri 11/7Mon 11/10
SJU - PWM • 1 stop
Cheapest one-way
$187
Typical prices: $211-$218
Southwest
Sat 2/28
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$187
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 51% 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 7984 reviews
7.9Comfort
7.3Food
8.2Boarding
8.5Crew
7.9Entertainment
Airline reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

2.0 MediocreRyan, Oct 2025FCO - JFK
Read more Delta reviews

Crew blocked exits to front of ship with galley carts. Also split five person family apart on international flight without fixing.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

On time flight. Seat comfort could be better in the Comfort section.

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

During booking, I kept trying submitting my payment from the Mexican website and it didn't work. After I had the idea to change it to the Canadian website, it worked but I had to be charged the equivalent of 50 CAD more. I received the clear instruction that I would only be able to check-in at the airport and that it was impossible to select a seat 24 hours before departure, that I had to pay 144 CAD to do so, although not only was I able to check-in 24 hours before departure, but I could have selected my seats for free then. All in all, I almost threw $200 out the window due to misleading information. Besides, the app kept crashing, the information to get to the gate on the app was inaccurate, my gate was switched and I was only informed once in the air (luckily I had noticed the departure pannel), I was not addressed in my language beforehand and even if I tried I was immediately answered in English (which meant the crew understood but didn't want to answer accordingly), there was only one snack & beverage service on my medium haul flight and no beverage service on my short haul flight. To be fair, the planes were comfortable, the crew apart from the language issue was helpful, dynamic and engaging, the plane was clean and the directions were clear and direct. United has a lot of potential to be one of my favourite airlines, but the devil is in the details and a lot of them missed the target.

Flight was timely, relatively comfortable, with decent entertainment and food served. Only problem encountered was with the free messaging which I highly appreciate, but it did not work from iphone to non-iphones.

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

The entertainment available didn’t work for anyone on the flight. Long 6 hr flight with no entertainment option and the staff didn’t know until an hour into the flight when we made sure they knew about it. They had no way to fix it.

Crew seemed a bit cranky. No seatback screens. But boarding was efficient and on time and we arrived early.

The worst landing I have ever had on a domestic flight. Thought we would lose the landing gear on landing in Newark. Then we spent 40 minutes trying to position the plane in the right place to be able to get the jet way to the plane. The plane arrived stopped. The announcer was that we were there. Everybody got up, then we were told to sit back down because they had to have us towed to a different position. We got towed and then everyone stood up and they told us we were in the wrong position to sit back down again, and then we got towed to a different position This did not happen immediately. It was 30 minutes while we wandered around a small section of the tarmac in Newark close to the gate, but apparently not close enough. Horrifying experience The CAB should be investigating that flight

Boarding was organized. Plane seats comfortable and service was attentive. Food options were good.

This was a very average flight. The seat was out of alignment so more uncomfortable than usual. The cabin felt not well maintained. But I safely got where I needed to go.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

Flight attendants on this flight were very attentive and friendly

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

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