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Find cheap flights from Connecticut to Caribbean from $59

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Connecticut to Caribbean departing on 5/18. 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
Sun 5/19
Sun 5/26

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Good to know

Low season

September

High season

December

Cheapest flight

$59
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 29% increase in price.
Flight from Hartford to San Juan Airport

FAQs for booking flights from Connecticut to Caribbean

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

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

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

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

 
Need help choosing which airline to fly with from Connecticut 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.
9.1
Cape AirOverall score based on 58 reviews
9.1entertainment
8.9boarding
8.4comfort
8.8food
9.5crew
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"

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

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

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

Easy boarding and deplaning. Short flight. Water was given but that was it.

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.

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

Book cheap flights from Connecticut to Caribbean

Recent round-trip flight deals

4/29Mon
nonstopFrontier
3h 48mBDL-SJU
5/3Fri
nonstopFrontier
3h 59mSJU-BDL
$118
4/30Tue
nonstopFrontier
3h 48mBDL-SJU
5/3Fri
nonstopFrontier
3h 59mSJU-BDL
$119
4/29Mon
nonstopFrontier
3h 48mBDL-SJU
5/2Thu
nonstopFrontier
3h 59mSJU-BDL
$120
6/1Sat
nonstopJetBlue
3h 52mBDL-SJU
6/4Tue
nonstopJetBlue
4h 06mSJU-BDL
$219
5/4Sat
nonstopJetBlue
3h 51mBDL-SJU
5/10Fri
nonstopJetBlue
4h 06mSJU-BDL
$252
6/3Mon
1 stopAmerican Airlines
14h 33mBDL-NAS
6/8Sat
1 stopAmerican Airlines
14h 51mNAS-BDL
$288
9/7Sat
1 stopAmerican Airlines
6h 54mBDL-NAS
9/12Thu
1 stopAmerican Airlines
7h 25mNAS-BDL
$316
6/1Sat
1 stopUnited Airlines
5h 38mBDL-NAS
6/8Sat
1 stopUnited Airlines
10h 43mNAS-BDL
$359
6/4Tue
2 stopsUnited Airlines
15h 53mBDL-NAS
6/8Sat
1 stopUnited Airlines
10h 43mNAS-BDL
$364
6/28Fri
2 stopsCopa Airlines
29h 15mBDL-SDQ
7/10Wed
2 stopsCopa Airlines
33h 17mSDQ-BDL
$1,430

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Recent one-way flight deals

5/18Sat
2 stopsFrontier
12h 27mBDL-SJU
$59
4/30Tue
nonstopFrontier
3h 48mBDL-SJU
$60
5/1Wed
nonstopFrontier
3h 48mBDL-SJU
$65
5/28Tue
1 stopAmerican Airlines
7h 46mBDL-NAS
$90
5/29Wed
nonstopJetBlue
3h 51mBDL-SJU
$110
5/15Wed
1 stopAmerican Airlines
11h 26mBDL-SJU
$113
8/14Wed
nonstopJetBlue
3h 53mBDL-SJU
$129
7/15Mon
1 stopUnited Airlines
10h 06mBDL-MBJ
$200
10/15Tue
1 stopUnited Airlines
6h 40mBDL-PUJ
$223
6/28Fri
2 stopsCopa Airlines
20h 13mBDL-PUJ
$282

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Last minute flights from Connecticut to Caribbean

Last minute flight, train and bus deals

4/23Tue
multi-stopFrontier
11h 55mBDL-SJU
5/3Fri
nonstopFrontier
3h 59mSJU-BDL
$166
4/22Mon
multi-stopFrontier
7h 41mBDL-SJU
5/2Thu
nonstopFrontier
3h 59mSJU-BDL
$169
4/24Wed
nonstop
3h 48mBDL-SJU
4/26Fri
multi-stop
8h 30mSJU-BDL
$223
4/24Wed
multi-stop
7h 11mBDL-SJU
5/6Mon
multi-stop
14h 01mSJU-BDL
$225
4/23Tue
nonstopJetBlue
3h 54mBDL-SJU
5/2Thu
nonstopJetBlue
4h 03mSJU-BDL
$292
4/24Wed
multi-stopAmerican Airlines
11h 40mBDL-SJU
4/27Sat
multi-stopAmerican Airlines
6h 31mSJU-BDL
$300
4/23Tue
multi-stopAmerican Airlines
9h 35mBDL-SJU
5/3Fri
multi-stopAmerican Airlines
6h 51mSJU-BDL
$301
4/24Wed
nonstopJetBlue
3h 54mBDL-SJU
4/30Tue
nonstopJetBlue
4h 03mSJU-BDL
$312
4/20Sat
multi-stopUnited Airlines
14h 32mBDL-SJU
4/27Sat
multi-stopUnited Airlines
14h 19mSJU-BDL
$403
4/23Tue
multi-stopUnited Airlines
9h 45mBDL-AUA
4/25Thu
multi-stopUnited Airlines
19h 20mAUA-BDL
$733

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