$192 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 5/6. 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

Sat, May 23 - Sat, May 30
United Airlines Logo
1:52 pm - 11:53 pm
MBJ
-
PDX
12h 01m
1 stop
United Airlines Logo
7:13 am - 3:26 pm
PDX
-
MBJ
30h 13m
1 stop
$374United Airlines
Thu, May 21 - Thu, May 28
United Airlines Logo
4:12 pm - 10:48 pm
MBJ
-
PDX
32h 36m
2 stops
United Airlines Logo
2:12 pm - 3:10 pm
PDX
-
MBJ
22h 58m
2 stops
$437United Airlines
Thu, May 7 - Tue, May 12
Delta Logo
1:16 pm - 11:44 pm
SJU
-
PDX
13h 28m
2 stops
Delta Logo
5:51 pm - 12:01 pm
PDX
-
SJU
15h 10m
2 stops
$476Delta
Tue, Sep 15 - Fri, Sep 18
Southwest Logo
5:15 am - 3:00 pm
SJU
-
PDX
12h 45m
2 stops
Southwest Logo
10:45 pm - 2:00 pm
PDX
-
SJU
12h 15m
2 stops
$478Southwest
Thu, Apr 30 - Tue, May 5
American Airlines Logo
1:31 pm - 11:53 pm
SJU
-
PDX
13h 22m
1 stop
American Airlines Logo
6:00 am - 11:02 pm
PDX
-
SJU
14h 02m
1 stop
$493American Airlines
Thu, May 7 - Tue, May 12
Delta Logo
2:35 pm - 10:02 pm
SJU
-
PDX
10h 27m
1 stop
Delta Logo
7:00 am - 11:35 pm
PDX
-
SJU
13h 35m
1 stop
$496Delta
Sat, Apr 25 - Wed, Apr 29
American Airlines Logo
11:38 am - 10:57 pm
SJU
-
PDX
14h 19m
2 stops
American Airlines Logo
7:23 am - 11:02 pm
PDX
-
SJU
12h 39m
2 stops
$501American Airlines
Wed, May 27 - Wed, Jun 3
Multiple Airlines Logo
6:41 pm - 11:50 am
SJU
-
PDX
68h 09m
3 stops
Multiple Airlines Logo
5:50 pm - 2:08 am
PDX
-
SJU
29h 18m
3 stops
$513Multiple Airlines
Fri, May 8 - Fri, May 15
Southwest Logo
2:05 pm - 12:10 am
PUJ
-
PDX
13h 05m
2 stops
Southwest Logo
11:55 pm - 3:00 pm
PDX
-
PUJ
12h 05m
1 stop
$688Southwest
Mon, Jun 15 - Sun, Jul 5
Multiple Airlines Logo
6:51 pm - 1:05 pm
PUJ
-
PDX
21h 14m
1 stop
Multiple Airlines Logo
3:30 pm - 3:15 pm
PDX
-
PUJ
20h 45m
2 stops
$811Multiple Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$192
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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 8406 reviews
7.9Comfort
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

The flight was smooth, the crew was great but the plane was quite old

8.0 ExcellentDimitrina, Apr 2026
BOS - DCA
Read more Delta reviews

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Great flight. Got to watch a movie. Smooth flight and early arrival at ORD.

This was the first flight in the morning. We boarded fine. The cabin door was closed and we were ready to go. We were notified by the Captain that ATC issued and ground stop for 40 minutes. So, without even pushing back from the gate, we were already 40 minutes late. We actually were released to push-back and taxi at 30 minutes. But, some passengers had tight connections and were not going to make their connections. Some passengers asked about the delay and the effect on the connections and were told by the cabin attendant that all flights will be delayed and so they should be OK. However, that was not true. My connecting flight was on time and I arrived at IAH with 21 minutes to make my connection. I did and I'm happy about that, but the flight crew should not have given assurances to the passengers who might have missed their connections.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

After arriving in Chicago, we were taxiing for 1.5 hours with infrequent and untruthful updates about the amount of time it would take to arrive at the gate. Minimally, the team could have provided timing expectations that were more truthful, especially one their original expectations were not met.

The crew was generally professional. Though one of the crew members seemed to be easily annoyed, the others were fine and helpful. The green olives and almonds snack was really good. A great idea, and nice balance of tastes.

It as confusing with the connections and I almost missed my next flight because of the first delay with the first flight. United could have helped passengers go through immigration quicker rather than waiting with everyone else. The flight attendants were super friendly and lovely. The vegetarian food was awful- I did not finish. I would suggest they just do pasta next time

Flights were on time actually early service was good and crew cheerful

Every staff member was professional, friendly and courteous. The pizza twist was ok. It was warm but too much dough.

I had a terrible experience. My flight got delayed from Atlanta to Chicago on Monday April 6, 2026, and that led to me missing my next flight to Brussels. United Airlines didn’t provide me with any accommodation for shelter. I had to sleep at the airport in Chicago. The next flight I was put on didn’t leave until the evening hours of Tuesday 4/7/2026.

THe flight was an hour late. You got us on the plan and we sat on the ground for 45 minutes with no information from the pilot whatsoever. Worst flight this year.

Boarding was quick and efficient. We arrived at our destination early.

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.

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