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Caribbean Islands

$82+ 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 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Oct 25 — Nov 11
Sat 10/25
Sat 11/1
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 September 25, 2025.

Round-trip from

$161
(CheapOair)

One-way from

$82
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$246
From Tweed-New Haven to Caribbean Islands
Search Deals
One-way flight from Tweed-New Haven to Caribbean Islands
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Highest demand for flights based on searches. 6% potential increase in price ($20 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 25, 2025.

This Mytrip deal was found by Cheapflights users on 9/23. 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.
Sat 11/19:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
Wed 11/57:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$158
This CheapOair deal was found by Cheapflights users on 9/25. 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.
Tue 12/28:59 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Fri 12/127:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/25$161
This CheapOair deal was found by Cheapflights users on 9/24. 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.
Sun 11/238:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Tue 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/24$164
This Trip.com deal was found by Cheapflights users on 9/23. 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.
Fri 11/148:30 pmHVN - SJU
1 stop15h 04mAvelo Airlines
Wed 11/191:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$194
This CheapOair deal was found by Cheapflights users on 9/22. 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.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/22$196
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Wed 10/298:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
Wed 11/57:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$197
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Thu 11/208:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$216
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Thu 11/208:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Mon 12/87:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$218
This CheapOair deal was found by Cheapflights users on 9/23. 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.
Mon 12/82:11 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Mon 12/157:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 9/23$219
This Mytrip deal was found by Cheapflights users on 9/24. 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.
Wed 10/2210:15 amHVN - STT
2 stops26h 44mMultiple Airlines
Wed 10/2911:01 amSTT - HVN
2 stops26h 02mMultiple Airlines
Deal found 9/24$460
This Mytrip deal was found by Cheapflights users on 9/25. 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.
Sun 11/94:15 pmHVN - PUJ
2 stops19h 01mMultiple Airlines
Sun 11/161:21 pmPUJ - HVN
2 stops24h 21mMultiple Airlines
Deal found 9/25$472
This Mytrip deal was found by Cheapflights users on 9/24. 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.
Sun 10/264:25 pmHVN - PUJ
2 stops22h 35mMultiple Airlines
Tue 11/44:57 pmPUJ - HVN
2 stops21h 17mMultiple Airlines
Deal found 9/24$478

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 September 25, 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

Wed 2/18

6:30 am-11:20 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 2/25

12:20 pm-3:25 pm

Nonstop4h 05m

$181

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 11/12

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Wed 11/19

1:24 pm-4:25 pm

Nonstop4h 01m

$190

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 11/15

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 11/23

3:44 am-6:45 am

Nonstop4h 01m

$196

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 2/22

8:59 pm-1:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 2/28

12:20 pm-3:25 pm

Nonstop4h 05m

$197

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 2/6

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Thu 2/12

3:40 am-6:45 am

Nonstop4h 05m

$204

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Tue 12/2

8:59 pm-1:53 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Mon 12/8

7:58 pm-10:59 pm

Nonstop4h 01m

$218

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/9

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 1/16

7:54 pm-10:59 pm

Nonstop4h 05m

$233

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 11/19

7:30 am-12:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sat 11/22

1:24 pm-4:25 pm

Nonstop4h 01m

$234

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 12/12

2:11 pm-7:05 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 12/18

3:44 am-6:45 am

Nonstop4h 01m

$244

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 10/22

8:50 am-12:41 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Wed 10/29

1:41 pm-5:48 pm

Nonstop4h 07m

$248

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/23

Showing 1-10 of 39 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 September 25, 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.

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 September 25, 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
2,914 reviews

Boarding

7.4

Comfort

7.6

Food

6.7

Crew

8.0

Entertainment

7.3

Overall

7.2

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
2,914 reviews
JetBlue
7.2
Good
2,914 reviews

Boarding

7.4

Comfort

7.6

Food

6.7

Crew

8.0

Entertainment

7.3

Overall

7.2

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.

  • How long is the flight from New Haven to Caribbean Islands?

    There are many flights that can get you from New Haven to Caribbean Islands in 3h 50m. Fly via Avelo Airlines to get the fastest option. Airlines will cover a distance of 1628 mi. All flights are typically nonstop.

  • 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 - 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 $252, our data indicates the cheapest price to be $77. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $158.

  • 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

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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 September 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$78Average$205FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$170Average$400FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$290FlexibilityNo cancel feeOn-timeN/A

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