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$60 Find cheap flights from Virginia to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Virginia to Caribbean departing on 6/27. 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 7/20
Sat 7/27

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Good to know

Low season

September

High season

December

Cheapest flight

$60
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 24% increase in price.
Flight from Raleigh to San Juan

FAQs for booking flights from Virginia to Caribbean

  • How does KAYAK find such low prices on flights from Virginia 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 Virginia to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Caribbean from Virginia 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 Virginia 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 Virginia with another airline.

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

Need help choosing which airline to fly with from Virginia 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 verified KAYAK customer reviews.
9.0
Cape AirOverall score based on 52 reviews
9.4Crew
8.3Comfort
8.7Food
9.0Entertainment
8.8Boarding
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"

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"

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.

Book cheap flights from Virginia to Caribbean

Recent round-trip flight deals

8/6Tue
nonstopFrontier
3h 28mRDU-SJU
8/8Thu
nonstopFrontier
3h 37mSJU-RDU
$130
7/9Tue
nonstopFrontier
3h 28mRDU-SJU
7/18Thu
nonstopFrontier
3h 37mSJU-RDU
$133
9/8Sun
nonstopJetBlue
3h 33mRDU-SJU
9/14Sat
1 stopJetBlue
5h 35mSJU-RDU
$212
9/12Thu
nonstopJetBlue
3h 33mRDU-SJU
9/19Thu
nonstopJetBlue
3h 42mSJU-RDU
$218
7/8Mon
nonstopAmerican Airlines
2h 46mDCA-NAS
7/10Wed
nonstopAmerican Airlines
2h 43mNAS-DCA
$268
9/11Wed
2 stopsAmerican Airlines
9h 08mRDU-SJU
9/21Sat
1 stopAmerican Airlines
13h 54mSJU-RDU
$270
10/1Tue
1 stopCopa Airlines
9h 46mIAD-AUA
10/7Mon
1 stopCopa Airlines
12h 30mAUA-IAD
$321
9/18Wed
1 stopCopa Airlines
12h 30mIAD-AUA
9/25Wed
1 stopCopa Airlines
14h 59mAUA-IAD
$337
10/5Sat
1 stopAvianca
19h 05mIAD-AUA
10/23Wed
1 stopAvianca
20h 05mAUA-IAD
$367
10/7Mon
2 stopsAvianca
17h 10mIAD-AUA
10/22Tue
1 stopAvianca
20h 05mAUA-IAD
$368

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Recent one-way flight deals

6/27Thu
nonstopFrontier
3h 17mRDU-SJU
$60
7/20Sat
nonstopFrontier
3h 28mRDU-SJU
$62
8/5Mon
2 stopsAmerican Airlines
18h 13mIAD-NAS
$94
9/4Wed
2 stopsAmerican Airlines
12h 25mDCA-NAS
$114
11/5Tue
1 stopJetBlue
6h 35mDCA-SJU
$127
7/19Fri
1 stopJetBlue
8h 07mRDU-SJU
$135
8/28Wed
1 stopCopa Airlines
12h 30mIAD-AUA
$153
10/9Wed
1 stopAvianca
19h 05mIAD-AUA
$160
8/30Fri
2 stopsAvianca
17h 10mIAD-AUA
$161
10/26Sat
1 stopCopa Airlines
9h 52mIAD-MBJ
$175

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Last minute flights from Virginia to Caribbean

Last minute flight, train and bus deals

6/24Mon
nonstopFrontier
3h 17mRDU-SJU
6/28Fri
nonstopFrontier
3h 40mSJU-RDU
$160
6/23Sun
nonstopFrontier
3h 17mRDU-SJU
6/28Fri
nonstopFrontier
3h 40mSJU-RDU
$170
6/23Sun
nonstopJetBlue
3h 44mRDU-SJU
6/25Tue
nonstopJetBlue
3h 45mSJU-RDU
$201
6/25Tue
nonstopJetBlue
3h 44mRDU-SJU
7/2Tue
nonstopJetBlue
3h 45mSJU-RDU
$231
6/24Mon
multi-stopAmerican Airlines
12h 30mRDU-SJU
6/28Fri
multi-stopAmerican Airlines
14h 43mSJU-RDU
$240
6/23Sun
multi-stopAmerican Airlines
11h 26mRDU-SJU
6/25Tue
multi-stopAmerican Airlines
12h 33mSJU-RDU
$245
6/23Sun
multi-stopCopa Airlines
9h 01mIAD-NAS
7/1Mon
multi-stopCopa Airlines
15h 40mNAS-IAD
$644
6/24Mon
multi-stopAvianca
24h 20mIAD-PUJ
8/26Mon
multi-stopAvianca
18h 15mPUJ-IAD
$675
6/25Tue
multi-stopAvianca
9h 35mIAD-PUJ
7/2Tue
multi-stopAvianca
18h 15mPUJ-IAD
$677
6/24Mon
multi-stopCopa Airlines
10h 44mIAD-PUJ
7/2Tue
multi-stopCopa Airlines
10h 35mPUJ-IAD
$824

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Flights to Caribbean

Return flight deals:

Caribbean - Virginia

Cabin classes:

$148