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Caribbean Islands

$108+ 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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Jun 27 — Jul 41
Fri 6/27
Fri 7/4
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 June 22, 2025.

Round-trip from

$200
(Travelocity)

One-way from

$108
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$255
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. 9% potential increase in price ($27 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 June 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 June 22, 2025.

This Travelocity deal was found by Cheapflights users on 6/21. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/38:59 pmHVN - SJU
Nonstop3h 46mAvelo Airlines
Thu 8/72:42 amSJU - HVN
Nonstop4h 03mAvelo Airlines
Deal found 6/21$200
This Trip.com deal was found by Cheapflights users on 6/21. 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.
Sun 8/174:30 pmHVN - SJU
1 stop10h 09mMultiple Airlines
Tue 8/198:13 pmSJU - HVN
1 stop18h 37mMultiple Airlines
Deal found 6/21$346
This Kiwi.com deal was found by Cheapflights users on 6/21. 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.
Mon 7/217:54 pmHVN - PUJ
1 stop15h 51mMultiple Airlines
Mon 7/2811:20 amPUJ - HVN
2 stops21h 25mMultiple Airlines
Deal found 6/21$465
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Fri 7/47:54 pmHVN - MBJ
1 stop18h 14mMultiple Airlines
Sat 8/22:09 pmMBJ - HVN
1 stop17h 36mMultiple Airlines
Deal found 6/20$476
This Kiwi.com deal was found by Cheapflights users on 6/20. 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.
Wed 6/254:00 pmHVN - NAS
1 stop26h 55mMultiple Airlines
Tue 7/14:25 pmNAS - HVN
1 stop16h 20mMultiple Airlines
Deal found 6/20$658

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 June 22, 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

Sun 8/3

8:59 pm-12:45 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Thu 8/7

2:42 am-6:45 am

Nonstop4h 03m

$200

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 8/17

4:30 pm-2:39 am

1 stop10h 09m

San Juan Luis Munoz Marin Intl

Tue 8/19

8:13 pm-2:50 pm

1 stop18h 37m

$346

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Mon 7/21

7:54 pm-11:45 am

1 stop15h 51m

Punta Cana

Mon 7/28

11:20 am-8:45 am

2 stops21h 25m

$465

New HavenMontego Bay

HVN - MBJ

HVNMBJ

Tweed-New Haven

Fri 7/4

7:54 pm-1:08 pm

1 stop18h 14m

Montego Bay Sangster Intl

Sat 8/2

2:09 pm-8:45 am

1 stop17h 36m

$476

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 8/24

8:59 pm-12:45 am

Nonstop3h 46m

$108

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 7/23

6:30 am-3:30 pm

1 stop9h 00m

$142

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/21

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 June 22, 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.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 22, 2025.
Avelo Airlines
7.4
Good

Comfort

7.1

Crew

8.2

Overall

7.4

Entertainment

5.0

Boarding

7.6

Food

5.1

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.
Avelo Airlines
7.4
Good
Avelo Airlines
7.4
Good

Comfort

7.1

Crew

8.2

Overall

7.4

Entertainment

5.0

Boarding

7.6

Food

5.1

Reviews

1 / 6
2.0
Mediocre

Cindy,Sep 2023

MCO - DAY

I was emailed and told that if I check my luggage early I get a 10 dollar discount, also on the website, if it's under 50 lbs. it would be $40.00 I was charged $65.00 on first flight and $60.00 on second flight (second flight I checked in early, did not receive the discount, both flights my luggage was under 40 lbs.). Avelo destroyed my luggage, wheels were tore off, and plastic was ripped off.

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 - Saint Thomas Island Cyril E King 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 $336, our data indicates the cheapest price to be $129. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $228.

  • 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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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 June 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$205FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$310FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$287FlexibilityNo cancel feeOn-timeN/A

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