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Caribbean Islands

$81+ 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 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
ago. 19 — ago. 261
mar. 8/19
mar. 8/26
1 adult, Economy
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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 agosto 14, 2025.

Round-trip from

$160
(CheapOair)

One-way from

$81
(Mytrip)

Popular in

December

Cheapest in

March

Average price

$328
From Tweed-New Haven to Caribbean Islands
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One-way flight from Tweed-New Haven to Caribbean Islands
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Highest demand for flights based on searches. 8% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 agosto 14, 2025.

This CheapOair deal was found by Cheapflights users on 8/13. 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.
sáb. 10/258:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
mié. 10/291:41 pmSJU - HVN
Nonstop4h 07mAvelo Airlines
Deal found 8/13$160
This CheapOair deal was found by Cheapflights users on 8/14. 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.
sáb. 10/118:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
sáb. 10/181:41 pmSJU - HVN
Nonstop4h 07mAvelo Airlines
Deal found 8/14$161
This CheapOair deal was found by Cheapflights users on 8/13. 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.
mié. 11/52:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
sáb. 11/87:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 8/13$189
This CheapOair deal was found by Cheapflights users on 8/13. 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.
sáb. 11/82:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
sáb. 11/157:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 8/13$190
This Mytrip deal was found by Cheapflights users on 8/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 10/52:15 pmHVN - SJU
3 stops23h 57mMultiple Airlines
sáb. 10/111:41 pmSJU - HVN
Nonstop4h 07mMultiple Airlines
Deal found 8/13$294
This Mytrip deal was found by Cheapflights users on 8/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/67:30 amHVN - SJU
2 stops28h 10mMultiple Airlines
mié. 11/127:54 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 8/13$300
This Mytrip deal was found by Cheapflights users on 8/14. 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.
mié. 8/277:00 amHVN - SJU
Nonstop3h 46mMultiple Airlines
mié. 9/106:44 amSJU - HVN
1 stop7h 36mMultiple Airlines
Deal found 8/14$301
This Trip.com deal was found by Cheapflights users on 8/13. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/123:40 pmHVN - SJU
1 stop9h 14mMultiple Airlines
vie. 9/196:44 amSJU - HVN
1 stop15h 06mMultiple Airlines
Deal found 8/13$302
This CheapOair deal was found by Cheapflights users on 8/13. 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.
mar. 11/258:59 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
dom. 11/303:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 8/13$305
This CheapOair deal was found by Cheapflights users on 8/14. 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.
lun. 12/152:11 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
sáb. 1/1012:28 pmSJU - HVN
Nonstop4h 05mAvelo Airlines
Deal found 8/14$333
This Mytrip deal was found by Cheapflights users on 8/12. 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.
vie. 9/262:40 pmHVN - SXM
2 stops23h 20mMultiple Airlines
vie. 10/33:05 pmSXM - HVN
2 stops21h 52mMultiple Airlines
Deal found 8/12$455
This Mytrip deal was found by Cheapflights users on 8/14. 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.
dom. 8/249:05 amHVN - NAS
2 stops25h 25mMultiple Airlines
sáb. 8/305:30 pmNAS - HVN
2 stops18h 53mMultiple Airlines
Deal found 8/14$560

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 agosto 14, 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

sáb. 10/25

8:50 am-12:41 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

mié. 10/29

1:41 pm-5:48 pm

Nonstop4h 07m

$160

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 11/8

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 11/15

7:54 pm-10:55 pm

Nonstop4h 01m

$161

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mié. 10/15

8:50 am-12:41 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

mié. 10/22

1:41 pm-5:48 pm

Nonstop4h 07m

$161

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 10/11

8:50 am-12:41 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

sáb. 10/18

1:41 pm-5:48 pm

Nonstop4h 07m

$161

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mié. 11/5

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 11/8

7:54 pm-10:55 pm

Nonstop4h 01m

$189

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

dom. 10/5

2:15 pm-2:12 pm

3 stops23h 57m

San Juan Luis Munoz Marin Intl

sáb. 10/11

1:41 pm-5:48 pm

Nonstop4h 07m

$294

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

jue. 11/6

7:30 am-12:40 pm

2 stops28h 10m

San Juan Luis Munoz Marin Intl

mié. 11/12

7:54 pm-10:55 pm

Nonstop4h 01m

$300

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mié. 8/27

7:00 am-10:46 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

mié. 9/10

6:44 am-2:20 pm

1 stop7h 36m

$301

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

vie. 9/12

3:40 pm-12:54 am

1 stop9h 14m

San Juan Luis Munoz Marin Intl

vie. 9/19

6:44 am-9:50 pm

1 stop15h 06m

$302

New HavenSimpson Bay

HVN - SXM

HVNSXM

Tweed-New Haven

vie. 9/26

2:40 pm-2:00 pm

2 stops23h 20m

Simpson Bay Princess Juliana

vie. 10/3

3:05 pm-12:57 pm

2 stops21h 52m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/13

Showing 1-10 of 22 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, September is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $254). Flying from New Haven to Caribbean Islands in June is currently the most expensive (average of $339). 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 agosto 14, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Haven to Caribbean Islands as you normally would.

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 - Kingston Norman Manley or Tweed-New Haven - Simpson Bay Princess Juliana 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 $347, our data indicates the cheapest price to be $256. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $160.

  • 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, September is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $254). Flying from New Haven to Caribbean Islands in June is currently the most expensive (average of $339). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for New Haven to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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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 agosto 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$195FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$310FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$287FlexibilityNo cancel feeOn-timeN/A

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