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Caribbean Islands

$106+ Cheap flights from New Haven (HVN) to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
déc. 13 — déc. 201
sam. 12/13
sam. 12/20
1 adult, Economy
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Find flight deals from New Haven to Caribbean Islands

Cheapest flights from New Haven to Caribbean Islands
Explore the most affordable flight options available from New Haven to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on novembre 13, 2025.

This CheapOair deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/208:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
ven. 12/127:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/12$199
This Mytrip deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 11/206:30 amHVN - SJU
1 stop16h 54mMultiple Airlines
ven. 12/127:58 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 11/12$206
This Mytrip deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/153:45 pmHVN - SJU
1 stop8h 00mMultiple Airlines
mer. 12/171:24 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 11/11$237
This CheapOair deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/197:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
ven. 12/57:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/12$244
This CheapOair deal was found by Cheapflights users on 11/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/197:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
mar. 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/13$248
This Mytrip deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 12/32:30 pmHVN - SJU
2 stops21h 02mMultiple Airlines
ven. 12/54:10 amSJU - HVN
1 stop10h 09mMultiple Airlines
Deal found 11/11$259
This Mytrip deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/197:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
dim. 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/12$272
This Mytrip deal was found by Cheapflights users on 11/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer. 11/193:55 pmHVN - SJU
2 stops27h 32mMultiple Airlines
dim. 11/233:44 amSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 11/12$278
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/2512:42 pmHVN - STT
1 stop24h 48mMultiple Airlines
mer. 12/33:25 pmSTT - HVN
1 stop28h 21mMultiple Airlines
Deal found 11/10$423
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 11/286:26 pmHVN - STT
2 stops19h 04mMultiple Airlines
mer. 12/33:25 pmSTT - HVN
1 stop28h 21mMultiple Airlines
Deal found 11/10$436
This Kiwi.com deal was found by Cheapflights users on 11/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dim. 11/307:26 pmHVN - STT
2 stops16h 29mMultiple Airlines
mer. 12/33:25 pmSTT - HVN
1 stop28h 21mMultiple Airlines
Deal found 11/10$508
This Mytrip deal was found by Cheapflights users on 11/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 12/277:45 amHVN - PUJ
1 stop13h 41mMultiple Airlines
mer. 12/316:08 pmPUJ - HVN
2 stops22h 27mMultiple Airlines
Deal found 11/11$522

Cheap flight deals from New Haven to Caribbean Islands

Keep the following information in mind while searching for New Haven to Caribbean Islands flight deals. Data was last updated novembre 13, 2025.

Round-trip from

$207
(CheapOair)

One-way from

$106
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$285
From Tweed-New Haven to Caribbean Islands
Search Deals
One-way flight from Tweed-New Haven to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($22 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Haven to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated novembre 13, 2025.
Use the filters below to find and compare flights from New Haven to Caribbean Islands that are best for you.

Fly from

New Haven

Fly to

Caribbean Islands

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

dim. 2/15

8:59 pm-1:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

mer. 2/18

1:22 pm-10:49 pm

1 stop10h 27m

$286

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

lun. 12/1

1:25 pm-11:44 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

mar. 12/2

3:44 am-6:45 am

Nonstop4h 01m

$305

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

ven. 12/5

3:45 pm-12:45 am

1 stop8h 00m

San Juan Luis Munoz Marin Intl

sam. 12/6

4:10 am-4:08 pm

2 stops12h 58m

$308

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

ven. 12/5

3:45 pm-12:45 am

1 stop8h 00m

San Juan Luis Munoz Marin Intl

lun. 12/8

7:58 pm-10:59 pm

Nonstop4h 01m

$326

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

dim. 12/7

7:00 am-12:32 pm

2 stops28h 32m

San Juan Luis Munoz Marin Intl

dim. 12/21

7:15 am-1:05 pm

1 stop6h 50m

$327

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mer. 1/21

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

sam. 1/24

6:00 am-2:23 pm

1 stop9h 23m

$338

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

jeu. 2/26

8:59 pm-1:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

lun. 3/2

4:55 pm-8:18 pm

3 stops28h 23m

$357

New HavenSaint Thomas Island

HVN - STT

HVNSTT

Tweed-New Haven

jeu. 11/27

7:26 pm-2:30 pm

1 stop18h 04m

Saint Thomas Island Cyril E King

mer. 12/3

3:25 pm-6:46 pm

1 stop28h 21m

$423

New HavenSaint Thomas Island

HVN - STT

HVNSTT

Tweed-New Haven

mar. 11/25

12:42 pm-2:30 pm

1 stop24h 48m

Saint Thomas Island Cyril E King

mer. 12/3

3:25 pm-6:46 pm

1 stop28h 21m

$423

New HavenSaint Thomas Island

HVN - STT

HVNSTT

Tweed-New Haven

ven. 11/28

6:26 pm-2:30 pm

2 stops19h 04m

Saint Thomas Island Cyril E King

mer. 12/3

3:25 pm-6:46 pm

1 stop28h 21m

$436

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 36 results
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Best time to book a flight from New Haven to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from New Haven with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from New Haven to Caribbean Islands

What is the cheapest month to book a flight from New Haven to Caribbean Islands?

Currently, February is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $59). Flying from New Haven to Caribbean Islands in August is currently the most expensive (average of $149). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from HVN to EPX?

Find hourly flight availability from New Haven to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated novembre 13, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 46% on flights from New Haven to Caribbean Islands by exploring options for tickets in the afternoon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated novembre 13, 2025.
Read through reviews of airlines operating flights from New Haven to Caribbean Islands, such as JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
JetBlue
7.2
Good
2,907 reviews

Crew

8.0

Overall

7.2

Entertainment

7.3

Boarding

7.4

Comfort

7.6

Food

6.7

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.
JetBlue
7.2
Good
2,907 reviews
JetBlue
7.2
Good
2,907 reviews

Crew

8.0

Overall

7.2

Entertainment

7.3

Boarding

7.4

Comfort

7.6

Food

6.7

Reviews

1 / 20
10.0
Excellent

JACK,Sep 2025

JFK - MSY

I liked the professional services of the crew. Keep up the good work.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from New Haven to Caribbean Islands?

    Most people fly from Tweed-New Haven (HVN) if they book a flight from New Haven to Caribbean Islands. Tweed-New Haven is conveniently located just 3.6 mi from New Haven’s city center.

  • What are the most popular routes from New Haven to Caribbean Islands?

    Most travelers choose Tweed-New Haven - San Juan Luis Munoz Marin Intl, Tweed-New Haven - Punta Cana or Tweed-New Haven - Willemstad Hato Int. when deciding on the best route from New Haven to Caribbean Islands.

  • What are the cheapest flights from New Haven to Caribbean Islands?

    Looking for the cheapest flight from New Haven to Caribbean Islands? While on average our users pay $222, our data indicates the cheapest price to be $112. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $199.

  • Can I find deals for flights from New Haven to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on New Haven to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from New Haven to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from New Haven to Caribbean Islands.

  • Can I find deals for business class flights from New Haven to Caribbean Islands?

    Yes. Cheapflights offers flight deals from New Haven to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from New Haven to Caribbean Islands?

    Currently, February is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $59). Flying from New Haven to Caribbean Islands in August is currently the most expensive (average of $149). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Top 3 airlines flying from New Haven to Caribbean Islands

Discover the top 3 airlines that operate flights from New Haven to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated novembre 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$211FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$464FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$286FlexibilityNo cancel feeOn-timeN/A

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