$239 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 7/29. 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

mié., oct. 28 - lun., nov. 2
United Airlines Logo
7:30 am - 6:13 pm
SJU
-
PWM
10h 43m
2 stops
United Airlines Logo
6:00 am - 2:40 pm
PWM
-
SJU
7h 40m
1 stop
$308United Airlines
vie., ago. 21 - sáb., ago. 29
Delta Logo
5:50 pm - 12:59 am
SJU
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PWM
7h 09m
1 stop
Delta Logo
6:05 am - 4:38 pm
PWM
-
SJU
10h 33m
1 stop
$312Delta
mié., oct. 28 - lun., nov. 2
Southwest Logo
5:35 am - 4:05 pm
SJU
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PWM
10h 30m
2 stops
Southwest Logo
5:20 am - 5:00 pm
PWM
-
SJU
10h 40m
2 stops
$332Southwest
vie., ago. 21 - sáb., ago. 29
American Airlines Logo
7:30 am - 10:00 pm
SJU
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PWM
14h 30m
1 stop
American Airlines Logo
7:28 am - 4:57 pm
PWM
-
SJU
9h 29m
2 stops
$337American Airlines
vie., ago. 21 - sáb., ago. 29
American Airlines Logo
7:30 am - 10:00 pm
SJU
-
PWM
14h 30m
1 stop
American Airlines Logo
6:00 am - 4:57 pm
PWM
-
SJU
10h 57m
2 stops
$347American Airlines
vie., oct. 23 - sáb., oct. 24
United Airlines Logo
1:25 pm - 11:59 pm
SJU
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PWM
10h 34m
2 stops
United Airlines Logo
6:00 am - 2:44 pm
PWM
-
SJU
8h 44m
1 stop
$348United Airlines
vie., oct. 23 - sáb., oct. 24
United Airlines Logo
1:25 pm - 11:59 pm
SJU
-
PWM
10h 34m
2 stops
United Airlines Logo
3:31 pm - 11:50 pm
PWM
-
SJU
8h 19m
1 stop
$402United Airlines
vie., ago. 21 - sáb., ago. 29
Southwest Logo
6:00 am - 3:00 pm
SJU
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PWM
9h 00m
2 stops
Southwest Logo
7:25 am - 6:05 pm
PWM
-
SJU
10h 40m
2 stops
$413Southwest
vie., oct. 16 - dom., oct. 18
American Airlines Logo
6:00 am - 11:24 pm
SJU
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PWM
17h 24m
1 stop
American Airlines Logo
6:00 am - 11:41 pm
PWM
-
SJU
17h 41m
1 stop
$417American Airlines
vie., ago. 21 - sáb., ago. 29
American Airlines Logo
10:33 am - 9:21 pm
SJU
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PWM
10h 48m
2 stops
American Airlines Logo
5:30 am - 4:57 pm
PWM
-
SJU
11h 27m
2 stops
$422American Airlines
Useful Info

Good to know

Cheapest flight$239
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 airline flying 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.
7.1
American AirlinesOverall score based on 11668 reviews
6.8Entertainment
7.2Comfort
7.5Boarding
7.9Crew
6.4Food
Airline reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

2.0 MediocreUzair, Jun 2026
SFO - JFK
Read more American Airlines reviews

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

The plane was comfortable but the crew wasn’t friendly.

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Crew was nice, aircraft dated, entertainment same. Internet is expensive and terribly slow. Food pretty bad

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