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Find cheap flights from New Haven to Caribbean Islands from $163

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Haven to Caribbean Islands departing on 6/30. 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
mar. 7/2
mar. 7/9

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Best Caribbean Islands Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Montego Bay
Montego Bay3 stops$764
Kingston
Kingston2 stops$561

Good to know

Low season

September

High season

February

Cheapest flight

$163
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from New Haven to San Juan

FAQs - booking Caribbean Islands flights

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

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

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

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New Haven 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 New Haven up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from New Haven to the following destinations at these prices or less: San Juan $231 one-way - $314 round-trip

Top airline flying from New Haven to Caribbean Islands

 
Need help choosing which airline to fly with from New Haven 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.
7.6
JetBlueOverall score based on 4346 reviews
7.8Comfort
7.8Boarding
8.3Crew
7.5Entertainment
7.1Food
Airline reviews

Overall fine but both ways for this trip was delayed.

6.0 GoodJackie, May 2024BOS - SYR
Read more about JetBlue reviews

Overall fine but both ways for this trip was delayed.

Flight was delayed by almost 5 hours. Suitcase was not loaded despite the flight being near empty (my colleagues’ suitcases did reach JFK, unlike mine). Had to argue on phone to get JetBlue to deliver the case to my hotel. Never again

The flight was excellent. The crew was welcoming and attentive.

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Book cheap flights from New Haven to Caribbean Islands

Recent round-trip flight deals

7/3mié.
1 stop
10h 45mHVN-SJU
7/9mar.
2 stops
17h 19mSJU-HVN
$330
6/12mié.
2 stops
21h 15mHVN-SJU
6/15sáb.
nonstop
4h 05mSJU-HVN
$339
6/12mié.
1 stop
8h 57mHVN-SJU
6/15sáb.
nonstop
4h 05mSJU-HVN
$341
6/12mié.
3 stops
30h 10mHVN-SJU
6/15sáb.
nonstop
4h 05mSJU-HVN
$349
7/5vie.
2 stops
22h 22mHVN-SJU
7/9mar.
1 stop
16h 29mSJU-HVN
$359
7/3mié.
2 stops
18h 37mHVN-SJU
7/9mar.
2 stops
17h 19mSJU-HVN
$360
6/17lun.
2 stops
23h 34mHVN-SJU
6/22sáb.
2 stops
16h 05mSJU-HVN
$362
7/5vie.
3 stops
28h 40mHVN-SJU
7/9mar.
1 stop
16h 29mSJU-HVN
$370
6/12mié.
nonstopAvelo Airlines
3h 55mHVN-SJU
6/15sáb.
nonstopAvelo Airlines
4h 05mSJU-HVN
$383
7/27sáb.
nonstopAvelo Airlines
3h 55mHVN-SJU
7/31mié.
nonstopAvelo Airlines
4h 05mSJU-HVN
$406

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Recent one-way flight deals

6/30dom.
2 stops
15h 55mHVN-SJU
$163
6/30dom.
3 stops
21h 36mHVN-SJU
$182
6/30dom.
1 stop
13h 48mHVN-SJU
$208
6/30dom.
2 stops
16h 43mHVN-KIN
$220
6/15sáb.
2 stops
21h 00mHVN-SJU
$222
6/15sáb.
2 stops
12h 24mHVN-SJU
$228
6/15sáb.
3 stops
16h 00mHVN-SJU
$239
6/15sáb.
3 stops
16h 00mHVN-SJU
$240
6/15sáb.
nonstopAvelo Airlines
3h 55mHVN-SJU
$276
6/8sáb.
nonstopAvelo Airlines
3h 55mHVN-SJU
$319

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Last minute flights from New Haven to Caribbean Islands

Last minute flight, train and bus deals

6/6jue.
multi-stop
9h 08mHVN-SJU
6/8sáb.
nonstop
4h 05mSJU-HVN
$409
6/6jue.
multi-stop
7h 47mHVN-SJU
6/8sáb.
multi-stop
9h 40mSJU-HVN
$446
6/6jue.
multi-stop
9h 08mHVN-SJU
6/8sáb.
multi-stop
28h 05mSJU-HVN
$484
6/6jue.
multi-stop
9h 08mHVN-SJU
6/8sáb.
multi-stop
28h 05mSJU-HVN
$515
6/6jue.
multi-stop
9h 08mHVN-SJU
6/7vie.
multi-stop
31h 15mSJU-HVN
$545
6/6jue.
multi-stop
18h 03mHVN-SJU
6/8sáb.
multi-stop
28h 05mSJU-HVN
$558
6/6jue.
multi-stop
18h 03mHVN-SJU
6/7vie.
multi-stop
31h 15mSJU-HVN
$588
6/6jue.
multi-stop
17h 03mHVN-SJU
6/8sáb.
multi-stop
28h 05mSJU-HVN
$610
6/6jue.
multi-stop
17h 03mHVN-SJU
6/7vie.
multi-stop
31h 15mSJU-HVN
$641

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