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Find cheap flights from Oregon to Caribbean from $129

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Oregon to Caribbean 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
0 bags
Sat 4/27
Sat 5/4

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Good to know

Low season

September

High season

December

Cheapest flight

$129
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly with an average 28% increase in price.
Flight from Portland to San Juan

FAQs for booking flights from Oregon to Caribbean

  • How does KAYAK find such low prices on flights from Oregon to Caribbean?

    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 Oregon to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Oregon to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Oregon 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 Oregon to Caribbean?

    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 Caribbean with an airline and back to Oregon with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Oregon to Caribbean?

    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 Caribbean from Oregon up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Oregon to Caribbean

Need help choosing which airline to fly with from Oregon to Caribbean? 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 KAYAK reviews.
9.0
Cape AirOverall score based on 60 reviews
95crew
89boarding
87food
84comfort
90entertainment
91overall
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

Read more about Cape Air

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Flight was delayed a bit since booking but otherwise everything was very good.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back

Thank you so much for initiating these much needle in state flights especially to Gainesville. Your service and personnel are ALL awesome.

Everything was great. Keep it going. You don’t need anything else. The flights are short and everyone is so solicitous. Thank you so much for getting these much needed flights

No comments, the complete handling and flying was excellent,keep up the good works.

Book cheap flights from Oregon to Caribbean

Recent round-trip flight deals

4/14Sun
2 stopsFrontier
17h 06mPDX-PUJ
4/20Sat
2 stopsFrontier
26h 33mPUJ-PDX
$276
4/14Sun
2 stopsFrontier
17h 06mPDX-PUJ
4/20Sat
2 stopsFrontier
26h 33mPUJ-PDX
$280
4/30Tue
2 stopsSpirit Airlines
16h 41mPDX-SJU
5/14Tue
2 stopsSpirit Airlines
24h 33mSJU-PDX
$285
5/18Sat
2 stopsSpirit Airlines
15h 22mPDX-SJU
5/22Wed
2 stopsSpirit Airlines
14h 35mSJU-PDX
$305
4/27Sat
1 stopAmerican Airlines
19h 31mPDX-SJU
5/5Sun
1 stopAmerican Airlines
15h 09mSJU-PDX
$428
9/11Wed
2 stopsAmerican Airlines
27h 45mPDX-SJU
9/17Tue
2 stopsAmerican Airlines
24h 25mSJU-PDX
$448
6/3Mon
1 stopJetBlue
13h 49mPDX-SJU
6/11Tue
1 stopJetBlue
13h 47mSJU-PDX
$473
4/10Wed
1 stopUnited Airlines
11h 50mPDX-NAS
4/17Wed
1 stopUnited Airlines
9h 28mNAS-PDX
$527
9/11Wed
3 stopsUnited Airlines
16h 52mPDX-SJU
9/16Mon
1 stopUnited Airlines
11h 18mSJU-PDX
$539
4/14Sun
1 stopJetBlue
13h 26mPDX-AUA
4/23Tue
1 stopJetBlue
12h 02mAUA-PDX
$546

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Recent one-way flight deals

5/6Mon
2 stopsFrontier
21h 57mPDX-SJU
$129
6/25Tue
1 stopFrontier
9h 47mPDX-SJU
$145
4/30Tue
3 stops
15h 03mPDX-SJU
$152
4/20Sat
1 stopAmerican Airlines
19h 31mPDX-SJU
$153
5/11Sat
1 stopAmerican Airlines
19h 46mPDX-SJU
$154
5/7Tue
2 stops
24h 02mPDX-SJU
$155
4/17Wed
1 stopJetBlue
12h 20mPDX-SJU
$195
4/9Tue
1 stopJetBlue
13h 26mPDX-AUA
$223
7/5Fri
1 stopUnited Airlines
11h 45mPDX-GCM
$260
8/23Fri
3 stopsUnited Airlines
20h 30mPDX-SJU
$425

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Last minute flights from Oregon to Caribbean

Last minute flight, train and bus deals

4/2Tue
multi-stopSpirit Airlines
24h 52mPDX-STT
4/23Tue
multi-stopSpirit Airlines
20h 49mSTT-PDX
$589
4/2Tue
multi-stopDelta
19h 45mPDX-AUA
4/21Sun
multi-stopDelta
20h 34mAUA-PDX
$646
4/2Tue
multi-stopSpirit Airlines
24h 52mPDX-STT
4/23Tue
multi-stopSpirit Airlines
32h 53mSTT-PDX
$660
3/31Sun
multi-stop
16h 35mPDX-NAS
4/6Sat
multi-stop
16h 43mNAS-PDX
$694
3/31Sun
multi-stopAir Canada
21h 10mPDX-NAS
4/6Sat
multi-stopAir Canada
25h 05mNAS-PDX
$711
4/2Tue
multi-stopUnited Airlines
10h 20mPDX-AUA
4/21Sun
multi-stopUnited Airlines
22h 42mAUA-PDX
$756
4/2Tue
multi-stopAmerican Airlines
9h 53mPDX-STT
4/23Tue
multi-stopAmerican Airlines
21h 15mSTT-PDX
$758
4/2Tue
multi-stop
29h 55mPDX-AUA
4/21Sun
multi-stop
32h 50mAUA-PDX
$771
3/29Fri
multi-stopAmerican Airlines
9h 47mPDX-SJU
4/5Fri
multi-stopAmerican Airlines
12h 34mSJU-PDX
$775
4/2Tue
multi-stopUnited Airlines
10h 20mPDX-AUA
4/21Sun
multi-stopUnited Airlines
31h 36mAUA-PDX
$804

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