$141 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 4/17. 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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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

Wed, Apr 22 - Sun, Apr 26
Delta Logo
7:15 am - 2:11 pm
SJU
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PWM
6h 56m
1 stop
Delta Logo
5:21 am - 1:25 pm
PWM
-
SJU
8h 04m
1 stop
$282Delta
Fri, May 1 - Mon, May 4
United Airlines Logo
4:55 pm - 11:59 pm
SJU
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PWM
7h 04m
1 stop
United Airlines Logo
9:00 am - 9:24 pm
PWM
-
SJU
12h 24m
2 stops
$302United Airlines
Wed, May 6 - Wed, May 13
American Airlines Logo
1:25 pm - 11:27 pm
SJU
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PWM
10h 02m
1 stop
American Airlines Logo
6:00 am - 12:35 pm
PWM
-
SJU
6h 35m
1 stop
$307American Airlines
Tue, Apr 21 - Sun, Apr 26
United Airlines Logo
1:00 am - 9:25 am
SJU
-
PWM
8h 25m
1 stop
United Airlines Logo
6:00 am - 8:34 pm
PWM
-
SJU
14h 34m
2 stops
$322United Airlines
Wed, Apr 29 - Tue, May 5
American Airlines Logo
6:00 am - 11:27 pm
SJU
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PWM
17h 27m
1 stop
American Airlines Logo
10:47 am - 8:51 pm
PWM
-
SJU
10h 04m
2 stops
$348American Airlines
Fri, May 1 - Sun, May 3
United Airlines Logo
7:20 am - 9:19 pm
SJU
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PWM
13h 59m
2 stops
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
$361United Airlines
Wed, Jun 3 - Sat, Jun 6
JetBlue Logo
6:30 am - 1:35 pm
SJU
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PWM
7h 05m
1 stop
JetBlue Logo
2:37 pm - 10:53 pm
PWM
-
SJU
8h 16m
1 stop
$371JetBlue
Fri, May 1 - Tue, May 5
United Airlines Logo
4:55 pm - 11:59 pm
SJU
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PWM
7h 04m
1 stop
United Airlines Logo
6:00 am - 1:45 pm
PWM
-
SJU
7h 45m
1 stop
$392United Airlines
Thu, Apr 30 - Mon, May 4
United Airlines Logo
1:00 am - 10:18 am
SJU
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PWM
9h 18m
2 stops
United Airlines Logo
9:00 am - 9:24 pm
PWM
-
SJU
12h 24m
2 stops
$405United Airlines
Wed, Aug 5 - Thu, Aug 13
United Airlines Logo
1:00 am - 9:11 am
SJU
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PWM
8h 11m
1 stop
United Airlines Logo
5:15 am - 8:38 pm
PWM
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SJU
15h 23m
2 stops
$413United Airlines
Useful Info

Good to know

Cheapest flight$141
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 11560 reviews
7.5Boarding
6.4Food
7.2Comfort
7.9Crew
6.9Entertainment
Airline reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

2.0 MediocreMark, Apr 2026
PHX - ORD
Read more American Airlines reviews

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Same plane as RDU to LGA — internet not working. Pilot issue of some sort at end of prior flight - I was on same plane for my connection. Late/delayed —

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Message about flight cancelation was received late due to being in the air. No explanation, just canceled and booked on morning flight. We had to stay in the airport overnight because there was no transportation offered to get to the hotel that AA had available. Actual inflight was fine.

Buying ticket from kayak instant booking was a huge mistake, never to be repeated again! The Kayak didn’t book the tickets directly, it handed it off to a third party Underpricer, that booked a code shared American Airlines flight operated by Cathay Pacific!! When managing the booking American Airlines would recognize the itinerary but wouldn’t let me do anything stating, the flight is operated by Cathay Pacific so go to their website. Cathay Pacific would recognize the itinerary, neither by reservation ID or ticket number…asking to reach out to the third party Underpricer….calling Underpricer resulted in no help like seat requests, mileage number or upgrade request, 15hr layover accommodation voucher guidance…so net in net avoid booking through three layers of intermediaries

I didn't go from Reno to Phoenix I ended up going from Reno to Dallas to Tucson because my flight rebooked because my Amtrak was late I tried notifying you guys I also don't know what you ask me about my flight because you guys didn't book my flight

A chaotic and uncomfortable experience from start to finish. The boarding process was a disaster; despite group numbers, it was a free-for-all that the staff failed to manage (especially after group 5). Once on board, the "entertainment" was non-existent. There are no seatback screens, and the mobile app selection is incredibly thin. The hardware is severely dated. My seat had zero cushioning left—it felt like sitting on a hard board for the entire flight—and the legroom was cramped. To make matters worse, the bathroom was repulsive, with toilet paper, soiled paper towels and liquid/pee all over the floor. When I did interact with the crew, they provided the absolute bare minimum and made me feel like an inconvenience for asking for anything. Avoid this flight if you can.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

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