$220 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 2/17. 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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Everything you should know

Cheapest round-trip
$440
Overall average: $605
American Airlines
Tue 2/10Sat 2/14
SJU - PDX • 2 stops
Cheapest one-way
$220
Typical prices: $250-$439
American Airlines
Tue 2/17
SJU - PDX • 1 stop
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Flight Deals
Useful Info
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

Tue, Feb 10 - Sat, Feb 14
American Airlines Logo
8:20 am - 8:27 pm
SJU
-
PDX
16h 07m
2 stops
American Airlines Logo
11:40 pm - 11:31 pm
PDX
-
SJU
19h 51m
1 stop
$440American Airlines
Tue, Mar 31 - Tue, Apr 14
American Airlines Logo
4:25 pm - 12:20 am
SJU
-
PDX
10h 55m
1 stop
American Airlines Logo
11:23 pm - 8:51 pm
PDX
-
SJU
18h 28m
1 stop
$478American Airlines
Tue, Feb 10 - Sat, Feb 14
American Airlines Logo
8:20 am - 8:27 pm
SJU
-
PDX
16h 07m
2 stops
American Airlines Logo
11:35 pm - 3:49 pm
PDX
-
SJU
12h 14m
2 stops
$494American Airlines
Fri, Mar 13 - Mon, Mar 16
Southwest Logo
1:05 pm - 12:45 am
SJU
-
PDX
14h 40m
2 stops
Southwest Logo
11:55 pm - 3:35 pm
PDX
-
SJU
12h 40m
2 stops
$531Southwest
Thu, Jun 25 - Tue, Jun 30
JetBlue Logo
1:09 pm - 10:03 pm
SJU
-
PDX
11h 54m
1 stop
JetBlue Logo
11:00 pm - 1:30 pm
PDX
-
SJU
11h 30m
1 stop
$540JetBlue
Tue, Feb 17 - Tue, Feb 24
United Airlines Logo
1:09 am - 3:27 pm
BQN
-
PDX
18h 18m
2 stops
United Airlines Logo
7:00 am - 11:57 pm
PDX
-
BQN
12h 57m
2 stops
$584United Airlines
Fri, Feb 13 - Mon, Feb 16
Southwest Logo
2:40 pm - 10:05 am
PLS
-
PDX
22h 25m
2 stops
Southwest Logo
6:50 pm - 1:45 pm
PDX
-
PLS
15h 55m
2 stops
$586Southwest
Thu, Apr 30 - Tue, May 5
United Airlines Logo
12:15 am - 12:48 am
BQN
-
PDX
27h 33m
2 stops
United Airlines Logo
5:15 am - 11:09 pm
PDX
-
BQN
14h 54m
2 stops
$596United Airlines
Thu, Jan 29 - Fri, Feb 6
Delta Logo
3:46 pm - 8:33 am
SDQ
-
PDX
20h 47m
2 stops
Delta Logo
7:00 am - 12:30 am
PDX
-
SDQ
13h 30m
1 stop
$674Delta
Sat, Feb 28 - Sat, Mar 7
Delta Logo
9:00 am - 10:08 pm
KIN
-
PDX
16h 08m
1 stop
Delta Logo
6:45 am - 8:00 pm
PDX
-
KIN
10h 15m
1 stop
$679Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$220
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 1% 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 4 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.
8.0
SouthwestOverall score based on 4260 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

3 hour delay. Had to change plans and was still delayed.

2.0 MediocreAnonymous, Jan 2026
SFO - SAN
Read more Southwest reviews

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

Staff was great! Kind and cordial! Middle seat row 28 seat B has a hump in it. Trays were getting stuck when putting down and up. Good flight

Departure was delayed resulting in me missing my connection. Delta did not autimatically find me another flight.

The seats weren’t reclining even though it wasn’t as exit seat

It was good because we traveled without luggage, carry on only.

We departed late, and we arrived to Atlanta late for our connecting flight to Quito. I asked the flight attendant before landing to please make an announcement and let us go out of the plane first she agreed but never did the announcement. We run and arrived 3 minutes late and they closed the gate of the plane. We ended up staying one day in Atlanta for the next flight to Quito. When we arrived to Quito 2 of our 50lbs bags arrived completely broken and destroyed. I made the complaint and so far nobody in Delta wants to help.

I usually get upgraded so my experience is usually amazing. I did not get upgraded this time - which was fine - but the wifi had issues, the monitors were going in & out, & (though not Delta's fault) one of the gentlemen next to me desperately needed a shower.

The entertainment screens were not working and there was no air condition the entire flight. Very uncomfortable.

I have diamond medallion status and usually we are in comfort plus . We were in main this time ( which was fine ) and my husband wanted wine . I have at least 10 vouchers for drinks that are good for this year and next! The attendant would not take the picture of the voucher as proof and never came back to check as She asked me to pull it up on delta Wi-Fi. Instead my husband just used his Amex to buy the wine . Disappointing!!!

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Safe made to destination. Late to start at GVA for icy reasons but we fought our next fly.

I just think it’s unfortunate that Airlines have completely abandoned the idea of serving any kind of decent or even real food on flights, not even on a four hour flight!? Those days are gone, I guess.

Yet another flight in which beverage and snack service was skipped. Other that that, firmly mediocre. Landed early, to gate late due to congestion at the gates. Airline's fault or airports fault: unknown.

Miserable. They moved my seat, but canceled the next leg of my flight. I resolved the issue at my transfer, but that resulted in lost luggage that has taken days off my schedule with no resolution. Worse, they fail to interface effectively with Lufthansa, forcing me to bounce between two equally useless help desks. The apps are unable to handle the situation, the bag dropped off the tracker, and while the call centers are polite, they do not provide written information to assist with cross-airline communication.

Both flights delayed. 2nd flight over 3 hours late mechanical issues

l really enjoy very much the flight was very pleasant

left on time, reasonable boarding process arrived early luggage came out quickly

I like flying first class, and United has a nice one

Flight was delayed 45 minutes because originating flight was coming from Newark. No complimentary snacks were offered on this 5+ hour flight. No screens for the flight, but movies offered if you had already downloaded the United app (which I hadn't on my ipad). No USB ports, only a flimsy plug-in port near the bottom of the seat that was hard to see and kept coming unplugged.

Delayed, no updates, had a rewards number but was not working

The seats from lax to DFW was so tight that I could not move my legs . No WiFi and had to pay . Not a good selection of entertainment

AA should improve their in air internet & entertainment options. Seems unreasonable to charge $20/hr and should have some form of free connections. The entertainment options are also pretty limited, movies are outdated and the series only show 3-5 episodes.

We were upgraded to First Class and it was a great flight

Amazing I love American. I’ll never fly anyone else if I can help it.

I love American. I’ll never fly anyone else if I can help it.

Flight delay and multiple gate changes including a change near boarding time to another terminal, which in DFW is a pain. Pre-boarding delay and also a further delay on the ground after boarding. About an hour and a half total delay.

On the plus side, crew was attentive, drinks were cold, and in-flight entertainment selection was better than some other airlines. On the negative aide, Plane was delayed almost an hour, either no announcements from the gate crew. Biscoff cookies are gross, appreciate airlines that give a choice. Also, crew had no personality or enthusiasm at all.

Little warm on the plane and delayed for an hour

Tell the crew (when boarding) to yell at the imbeciles blocking us from walking up to scan. I promise everyone crowds around and half of us (most the time I’m group 4) have to push our way through. Your staff is awesome, the public - not so much-

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