$188 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 3/19. 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
$232
American Airlines
Thu 2/26Tue 3/3
SJU - PWM • 2 stops
Cheapest one-way
$188
Typical prices: $303-$426
American Airlines
Thu 3/19
SJU - PWM • 1 stop
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Flight Deals
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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

Thu, Feb 26 - Tue, Mar 3
American Airlines Logo
2:30 pm - 11:50 pm
SJU
-
PWM
10h 20m
2 stops
American Airlines Logo
6:36 pm - 1:33 pm
PWM
-
SJU
17h 57m
2 stops
$232American Airlines
Thu, Feb 26 - Tue, Mar 3
Southwest Logo
5:45 pm - 11:50 pm
SJU
-
PWM
7h 05m
1 stop
Southwest Logo
3:30 pm - 11:10 pm
PWM
-
SJU
6h 40m
1 stop
$252Southwest
Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
7:40 am - 11:20 pm
SJU
-
PWM
16h 40m
2 stops
United Airlines Logo
3:05 pm - 12:36 am
PWM
-
SJU
8h 31m
1 stop
$255United Airlines
Fri, Mar 6 - Sun, Mar 8
Southwest Logo
6:20 pm - 12:05 am
SJU
-
PWM
6h 45m
1 stop
Southwest Logo
5:30 pm - 12:05 am
PWM
-
SJU
6h 35m
1 stop
$372Southwest
Thu, Mar 5 - Sun, Mar 8
United Airlines Logo
2:05 am - 10:49 am
SJU
-
PWM
9h 44m
1 stop
United Airlines Logo
6:00 am - 8:00 pm
PWM
-
SJU
14h 00m
2 stops
$388United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 2:39 pm
SJU
-
PWM
22h 47m
1 stop
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$472United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 2:39 pm
SJU
-
PWM
22h 47m
1 stop
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$507United Airlines
Fri, Mar 6 - Sun, Mar 8
Southwest Logo
2:05 pm - 12:05 am
SJU
-
PWM
11h 00m
2 stops
Southwest Logo
12:35 pm - 11:20 pm
PWM
-
SJU
10h 45m
2 stops
$516Southwest
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 1:56 pm
SJU
-
PWM
22h 04m
2 stops
United Airlines Logo
6:00 am - 9:00 pm
PWM
-
SJU
14h 00m
2 stops
$550United Airlines
Wed, Feb 4 - Sun, Feb 8
United Airlines Logo
4:52 pm - 2:39 pm
SJU
-
PWM
22h 47m
1 stop
United Airlines Logo
3:42 pm - 12:36 am
PWM
-
SJU
7h 54m
1 stop
$570United Airlines
Useful Info

Good to know

Cheapest flight$188
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 8094 reviews
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
7.9Comfort
Airline reviews

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

2.0 MediocreGary, Jan 2026
CLE - DTW
Read more Delta reviews

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Mean flight attendant. I wanted to reuse my plastic cup, but he (Matthew) said he can't for safety. I then said "I don't want water then" and he poured me a glass. I hope Matthew gets herpes and spends the rest of his life poor, lonely, and homeless.

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The seats were comfortable and we had leg room. Great entertainment.

The flight crew where really good. Better then the crew from BNE to SFO

Delayed, toilets did not flush, pilot parked to far away from Gate

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

This flight captain and crew were amazing, started ahead of time of departure and reached 30 mins before arrival time. Amazing!

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

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