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Find cheap flights from Oregon to Caribbean Islands from $138

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 Islands departing on 5/11. 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
Wed 6/5
Wed 6/12

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Good to know

Low season

September

High season

December

Cheapest flight

$138
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Portland to San Juan

FAQs for booking flights from Oregon to Caribbean Islands

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 3 airlines serving from Oregon to Caribbean Islands

 
Need help choosing which airline to fly with from Oregon to Caribbean Islands? 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.
9.0
Cape AirOverall score based on 57 reviews
8.9Boarding
8.4Comfort
9.5Crew
8.8Food
9.1Entertainment
Airline reviews

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

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

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"

Friendly staff, easy, and on time. Needs improvement on booking directly. Also

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

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"

Book cheap flights from Oregon to Caribbean Islands

Recent round-trip flight deals

5/29Wed
2 stopsSpirit Airlines
23h 46mPDX-SDQ
6/3Mon
2 stopsSpirit Airlines
21h 20mSDQ-PDX
$276
6/4Tue
2 stopsSpirit Airlines
17h 23mPDX-STT
6/11Tue
2 stopsSpirit Airlines
20h 19mSTT-PDX
$343
6/2Sun
2 stopsSpirit Airlines
23h 46mPDX-SDQ
6/9Sun
2 stopsSpirit Airlines
21h 43mSDQ-PDX
$348
5/14Tue
3 stopsSpirit Airlines
30h 05mPDX-SJU
5/25Sat
2 stopsSpirit Airlines
17h 23mSJU-PDX
$360
5/28Tue
2 stopsFrontier
31h 14mPDX-PUJ
6/3Mon
2 stopsFrontier
27h 56mPUJ-PDX
$372
5/28Tue
2 stopsFrontier
31h 14mPDX-PUJ
6/3Mon
2 stopsFrontier
29h 47mPUJ-PDX
$380
8/12Mon
2 stopsAmerican Airlines
19h 00mPDX-STT
8/20Tue
2 stopsAmerican Airlines
23h 51mSTT-PDX
$473
8/27Tue
2 stopsAmerican Airlines
21h 45mPDX-STT
9/5Thu
2 stopsAmerican Airlines
24h 26mSTT-PDX
$475
5/14Tue
1 stopJetBlue
12h 59mPDX-SJU
5/25Sat
1 stopJetBlue
13h 34mSJU-PDX
$517
9/5Thu
2 stopsCopa Airlines
42h 40mPDX-BGI
9/14Sat
2 stopsCopa Airlines
36h 51mBGI-PDX
$720

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Recent one-way flight deals

5/11Sat
1 stopSpirit Airlines
13h 01mPDX-SJU
$138
6/12Wed
1 stopSpirit Airlines
10h 09mPDX-SJU
$149
6/12Wed
2 stopsSpirit Airlines
27h 25mPDX-SJU
$150
8/23Fri
1 stopDelta
11h 27mPDX-SJU
$182
8/23Fri
2 stopsAmerican Airlines
22h 24mPDX-SJU
$200
10/4Fri
1 stopDelta
12h 30mPDX-AUA
$207
6/13Thu
2 stopsFrontier
27h 09mPDX-SJU
$217
6/12Wed
2 stopsFrontier
11h 09mPDX-SJU
$229
10/26Sat
2 stopsAmerican Airlines
19h 46mPDX-STT
$231
10/4Fri
1 stopJetBlue
10h 44mPDX-BGI
$392

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Last minute flights from Oregon to Caribbean Islands

Last minute flight, train and bus deals

5/11Sat
multi-stopFrontier
29h 46mPDX-PUJ
5/17Fri
multi-stopFrontier
26h 48mPUJ-PDX
$325
5/11Sat
multi-stopSpirit Airlines
13h 01mPDX-SJU
5/24Fri
multi-stopSpirit Airlines
21h 22mSJU-PDX
$383
5/11Sat
multi-stop
13h 01mPDX-SJU
5/19Sun
multi-stop
13h 58mSJU-PDX
$404
5/11Sat
multi-stop
13h 01mPDX-SJU
5/23Thu
multi-stop
12h 28mSJU-PDX
$434
5/11Sat
multi-stopDelta
13h 50mPDX-SDQ
5/16Thu
multi-stopDelta
19h 48mSDQ-PDX
$507
5/11Sat
multi-stopDelta
13h 50mPDX-SDQ
5/18Sat
multi-stopDelta
22h 59mSDQ-PDX
$519
5/9Thu
multi-stopAmerican Airlines
12h 50mPDX-SJU
5/11Sat
multi-stopAmerican Airlines
15h 08mSJU-PDX
$656
5/7Tue
multi-stopAmerican Airlines
11h 50mPDX-SJU
5/14Tue
multi-stopAmerican Airlines
12h 19mSJU-PDX
$689
5/10Fri
multi-stopUnited Airlines
12h 05mPDX-SJU
5/17Fri
multi-stopUnited Airlines
13h 33mSJU-PDX
$792
5/10Fri
multi-stopUnited Airlines
14h 04mPDX-SJU
5/17Fri
multi-stopUnited Airlines
13h 33mSJU-PDX
$845

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Flights to Caribbean Islands

Return flight deals:

Caribbean Islands - Oregon

Cabin classes:

$164
$298
$106
$38

Browse origins:

Browse destinations:

$379
Flights to Christiansted, Caribbean Islands
$1,646
Flights to Culebra, Caribbean Islands
$820
Flights to Fort-de-France, Caribbean Islands
$694
Flights to Freeport, City of Freeport, Caribbean Islands
$571
Flights to George Town, Caribbean Islands
$645
Flights to Georgetown, Caribbean Islands
$890
Flights to Governor’s Harbour, Caribbean Islands
$757
Flights to Gregory Town, Caribbean Islands
$331
Flights to Havana, Caribbean Islands
$748
Flights to Holguín, Caribbean Islands
$507
Flights to Kingston, Caribbean Islands
$726
Flights to Kralendijk, Caribbean Islands
$783
Flights to Marsh Harbour, Caribbean Islands
$465
Flights to Montego Bay, Caribbean Islands
$1,050
Flights to Nagua, Caribbean Islands
$452
Flights to Nassau, Caribbean Islands
$476
Flights to Oranjestad, Caribbean Islands
$464
Flights to Port Au Prince, Caribbean Islands
$661
Flights to Port of Spain, Caribbean Islands
$504
Flights to Providenciales, Caribbean Islands
$505
Flights to Puerto Plata, Caribbean Islands
$380
Flights to Punta Cana, Caribbean Islands
$672
Flights to Road Town, Caribbean Islands
$897
Flights to Rock Sound, Caribbean Islands
$446
Flights to Saint Thomas Island, Caribbean Islands
$984
Flights to Santa Clara, Villa Clara, Caribbean Islands
$495
Flights to Santiago de los Caballeros, Caribbean Islands
$500
Flights to Santo Domingo, Caribbean Islands
$401
Flights to Simpson Bay, Caribbean Islands
$671
Flights to St. George's, Caribbean Islands
$652
Flights to St. John's, Saint John, Caribbean Islands
$687
Flights to Varadero, Caribbean Islands
$3,426
Flights to Vieques, Caribbean Islands
$543
Flights to Willemstad, Caribbean Islands
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