$53 Find Cheap Flights from Vermont to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Vermont to Caribbean Islands departing on 12/31. 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.
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Good to know

Low season

September

High season

December

Cheapest flight

$53
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Hartford to San Juan Airport

FAQs for booking flights from Vermont to Caribbean Islands

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

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

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

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

Need help choosing which airline to fly with from Vermont 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.
8.9
Cape AirOverall score based on 39 reviews
8.9Entertainment
8.6Boarding
8.5Comfort
9.2Crew
8.6Food
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 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"

The flight was VERY, VERY hot and the blowers weren't cooling it off...don't know what the problem was, but.....otherwise it was fine.

My flight from Avianca was 45 minutes late and it's very complicated to recheck in in ...also I have to say the silver desk folks were neither efficient nor helpful...so I missed my connecting flight. I actually got there before tge flight left but they refused to let me on....and gave me no vouchers for hotel etc

The cancelled our flight 3 times and we never made it to our destination. Every single airplane had a maintenance problem. Never fly this airline

9 hrs wait in airport then flt redirected to airport an hour away from our booked airport. Then at 8:00pm flight Cancelled. Silver supposed to book us on American the next day. Booked my husband but not me. Cost me Ubers, hotel, meals, new ticket and 1 hour taxi Cuz no flights to our home airport. Absolute disaster. Silver staff had no idea what was going on or what to do. Never Again Silver

Nothing about this flight was good. They are always cancelling or grossly delayed. We were delayed for 45 minutes for no apparent reason with no explanation or anything we could see and I missed my connection to Durham NC. I was on my way to my best friends memorial and funeral. Now I'll missed them both!!

Total disaster! The easiest flight was kept delayed till … cancelled! And before official announcement of the flight cancellation I was offered to join ongoing boarding to FLL so I had to change all my traveling plans, have lost my car reservation and a payed spot at the meeting I was going for to begin with! I had to no show to my flight back, because it was from different airport again!

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.

Did not get to travel, you canceled my flight and left me stranded for the hole day, it's another day and I can't get to my destination. I will not recommend any one to this away, bad service

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."

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 Vermont to Caribbean Islands

Recent round-trip flight deals

12/11Wed
nonstopFrontier
3h 58mBDL-SJU
12/16Mon
1 stopFrontier
15h 36mSJU-BDL
$117
12/12Thu
nonstopFrontier
3h 58mBDL-SJU
12/16Mon
1 stopFrontier
15h 36mSJU-BDL
$124
12/9Mon
1 stop
13h 22mBDL-SJU
12/16Mon
1 stop
15h 36mSJU-BDL
$166
1/23Thu
1 stop
14h 35mBDL-SJU
1/28Tue
nonstop
4h 19mSJU-BDL
$167
12/10Tue
1 stopSpirit Airlines
27h 51mBDL-STT
12/13Fri
1 stopSpirit Airlines
11h 06mSTT-BDL
$236
1/23Thu
nonstopJetBlue
3h 46mBDL-SJU
1/26Sun
nonstopJetBlue
4h 04mSJU-BDL
$259
12/5Thu
2 stopsSpirit Airlines
19h 52mBDL-SJU
12/12Thu
1 stopSpirit Airlines
25h 49mSJU-BDL
$268
1/28Tue
1 stopJetBlue
8h 25mALB-SJU
2/6Thu
1 stopJetBlue
9h 50mSJU-ALB
$275
3/25Tue
2 stopsCopa Airlines
16h 26mBDL-AUA
3/30Sun
2 stopsCopa Airlines
17h 57mAUA-BDL
$583
4/21Mon
2 stopsCopa Airlines
20h 48mBDL-PUJ
4/26Sat
2 stopsCopa Airlines
16h 04mPUJ-BDL
$595

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Recent one-way flight deals

12/31Tue
nonstopFrontier
3h 58mBDL-SJU
$53
1/27Mon
1 stopFrontier
13h 49mBDL-SJU
$57
12/31Tue
nonstopFrontier
3h 58mBDL-SJU
$59
1/7Tue
1 stopSpirit Airlines
13h 22mBDL-SJU
$86
1/23Thu
1 stopSpirit Airlines
14h 35mBDL-SJU
$91
12/11Wed
nonstopAvelo Airlines
4h 10mBDL-MBJ
$99
12/31Tue
nonstopJetBlue
3h 47mBDL-SJU
$115
1/23Thu
nonstopJetBlue
3h 46mBDL-SJU
$130
11/27Wed
nonstopAvelo Airlines
4h 10mBDL-MBJ
$134
3/26Wed
2 stopsCopa Airlines
20h 44mBDL-PUJ
$286

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Last minute flights from Vermont to Caribbean Islands

Last minute flight, train and bus deals

11/24Sun
nonstopFrontier
3h 54mBDL-SJU
12/7Sat
nonstopFrontier
4h 07mSJU-BDL
$193
11/25Mon
nonstopFrontier
3h 54mBDL-SJU
11/27Wed
nonstopFrontier
4h 08mSJU-BDL
$204
11/27Wed
multi-stop
10h 49mBDL-SJU
12/4Wed
nonstop
4h 07mSJU-BDL
$258
11/27Wed
multi-stopSpirit Airlines
10h 49mBDL-SJU
12/4Wed
multi-stopSpirit Airlines
12h 02mSJU-BDL
$271
11/24Sun
nonstop
3h 54mBDL-SJU
12/3Tue
multi-stop
26h 23mSJU-BDL
$274
11/24Sun
multi-stopAmerican Airlines
11h 18mBDL-SJU
12/7Sat
multi-stopAmerican Airlines
17h 01mSJU-BDL
$296
11/26Tue
multi-stopSpirit Airlines
10h 49mBDL-SJU
12/3Tue
multi-stopSpirit Airlines
26h 23mSJU-BDL
$330
11/25Mon
multi-stopAmerican Airlines
10h 20mBDL-SJU
11/27Wed
multi-stopAmerican Airlines
8h 52mSJU-BDL
$344
11/27Wed
multi-stopJetBlue
7h 29mBDL-NAS
12/2Mon
multi-stopJetBlue
5h 06mNAS-BDL
$711
11/24Sun
multi-stopJetBlue
7h 40mALB-SJU
12/1Sun
multi-stopJetBlue
8h 28mSJU-ALB
$897

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Everything you need to know for your flight to Caribbean Islands

Cabin class types available on flights to Vermont

Cabin classes available on flights to Vermont. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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