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$65 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 8/10. 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 8/24
Sat 8/31

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Good to know

Low season

September

High season

December

Cheapest flight

$65
Best time to beat the crowds with an average 16% 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 4 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 51 reviews
9.0Entertainment
8.7Food
8.3Comfort
8.8Boarding
9.4Crew
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"

The worst experience we had traveling. The worst experience we have had traveling. The service is lousy, I will NEVER choose this airline again.

Never in time always late, even on arrival gate not ready so waited on tarmac another 45 min

Flight canceled 11 hours after being delayed. Miss annual family vacation because of this

This was a short flight so food was not offered. The stewardess was great at giving water out. The baggage check at the airport was hideous. One person was untrained and had asked a question. The other two people were just dealing. Someone could have worked the line and said you must have a luggage tag and you must have confirmation. We waited for some people at the counter for 20 minutes because they couldn't find their reservation or they were missing their luggage tags. We were in line an hour and 20 minutes had to run to her gate just to find out our flight was delayed 40 minutes. The silver air website never updated with status changes on the phone. Horribly irresponsible flight company.

I like that the crew member offered to hand me my carry in after I walked up the stairs

This Airline is horrible. I never made it to Orlando. Left after waiting for this flight since 11:45am. This flight was delayed 15 times up until 10:30pm. Boarded twice after pilot reported issues with the plane. After the the second boarding the pilot now reported ground stop in Orlando due to weather which was now at almost 5pm. This is ridiculous that passengers have to sit for all this time dealing with so many issues. Why wasn’t there another plane brought in before the weather became the third issue. Will never use this airline again. Awful. I hope I get my refund.

The flight attendant said I didn’t have a seat on the flight and made me miss the flight after 8 delays! When in fact I did have a seat and they sent me to a different airport with a different airline for the trip home! Never again!

Boarding started earlier but was not updated on any screen. We only heard the overhead call for final boarding. The plane sat on the tarmac for over an hour after landing.

Horrible and unprofessional staff. Plane was unkept and security lacking. Agents bickering over which one was going to print my boarding pass.

Besides there were several delays, they wouldn’t give me my boarding pass for both my connecting flights (even though due to the delays I had an extremely short time to get to my second flight). When I went to the counter at my connection, two agents were bickering about who was going to help me. One continued saying she was quitting and the other should tell their boss she’s not coming in the next day. Staff was extremely unprofessional, plane cleanliness and security was lacking. This was my first and last time using Silver Airlines.

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

9/13Fri
nonstopFrontier
3h 44mRDU-SJU
9/16Mon
nonstopFrontier
3h 53mSJU-RDU
$88
9/20Fri
nonstopFrontier
3h 44mRDU-SJU
9/27Fri
nonstopFrontier
3h 53mSJU-RDU
$90
8/23Fri
nonstopJetBlue
3h 42mRDU-SJU
8/30Fri
nonstopJetBlue
3h 45mSJU-RDU
$180
9/24Tue
1 stopAmerican Airlines
9h 53mRDU-SJU
9/28Sat
1 stopAmerican Airlines
6h 35mSJU-RDU
$188
8/24Sat
1 stopJetBlue
5h 42mRDU-SJU
8/27Tue
nonstopJetBlue
3h 45mSJU-RDU
$207
8/23Fri
nonstopAmerican Airlines
2h 50mDCA-NAS
8/30Fri
nonstopAmerican Airlines
2h 38mNAS-DCA
$278
8/25Sun
1 stopCopa Airlines
8h 36mIAD-PUJ
9/4Wed
1 stopCopa Airlines
22h 05mPUJ-IAD
$298
9/10Tue
1 stopCopa Airlines
9h 46mIAD-AUA
9/18Wed
1 stopCopa Airlines
14h 59mAUA-IAD
$321
10/2Wed
1 stopAvianca
19h 05mIAD-AUA
10/6Sun
1 stopAvianca
19h 10mAUA-IAD
$323
10/17Thu
2 stopsAvianca
12h 05mIAD-AUA
10/20Sun
1 stopAvianca
19h 10mAUA-IAD
$349

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Recent one-way flight deals

8/10Sat
nonstopFrontier
3h 49mRDU-SJU
$65
8/7Wed
nonstopFrontier
3h 48mRDU-SJU
$68
8/24Sat
nonstopAmerican Airlines
2h 50mDCA-NAS
$89
8/20Tue
nonstopJetBlue
3h 42mRDU-SJU
$90
8/7Wed
1 stopAmerican Airlines
4h 21mIAD-NAS
$93
10/27Sun
nonstopJetBlue
3h 29mRDU-SJU
$110
8/8Thu
1 stopCopa Airlines
18h 51mIAD-NAS
$122
10/22Tue
1 stopCopa Airlines
9h 46mIAD-AUA
$137
10/23Wed
1 stopAvianca
19h 05mIAD-AUA
$138
10/23Wed
2 stopsAvianca
17h 10mIAD-AUA
$139

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Last minute flights from Virginia to Caribbean

Last minute flight, train and bus deals

7/30Tue
nonstopFrontier
3h 28mRDU-SJU
8/7Wed
nonstopFrontier
3h 55mSJU-RDU
$141
7/28Sun
nonstopFrontier
3h 28mRDU-SJU
8/7Wed
nonstopFrontier
3h 55mSJU-RDU
$162
7/29Mon
nonstopJetBlue
3h 42mRDU-SJU
8/17Sat
multi-stopJetBlue
5h 40mSJU-RDU
$277
7/30Tue
nonstopJetBlue
3h 42mRDU-SJU
8/13Tue
nonstopJetBlue
3h 45mSJU-RDU
$300
7/27Sat
nonstopAmerican Airlines
2h 46mDCA-NAS
8/1Thu
nonstopAmerican Airlines
2h 43mNAS-DCA
$303
7/27Sat
multi-stopAmerican Airlines
4h 58mDCA-NAS
8/1Thu
nonstopAmerican Airlines
2h 43mNAS-DCA
$308
7/28Sun
multi-stopCopa Airlines
9h 00mIAD-NAS
8/5Mon
multi-stopCopa Airlines
15h 53mNAS-IAD
$527
7/30Tue
multi-stopCopa Airlines
14h 01mIAD-PUJ
8/4Sun
multi-stopCopa Airlines
16h 08mPUJ-IAD
$679
7/30Tue
multi-stopAvianca
12h 05mIAD-AUA
8/8Thu
multi-stopAvianca
19h 10mAUA-IAD
$757
7/29Mon
multi-stopAvianca
39h 05mIAD-AUA
8/8Thu
multi-stopAvianca
19h 10mAUA-IAD
$873

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Flights to Caribbean

Return flight deals:

Caribbean - Virginia

Cabin classes:

$160