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Caribbean Islands

$89+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Mar 16 — Mar 231
Mon 3/16
Mon 3/23
1 adult, Economy
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Cheap 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 February 14, 2026.

This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 5/612:05 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/10$157
This CheapOair deal was found by Cheapflights users on 2/9. 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 6/37:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 6/1012:05 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/9$169
This CheapOair deal was found by Cheapflights users on 2/12. 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.
Fri 6/58:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 6/1212:58 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/12$192
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/37:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Mon 6/812:58 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/11$193
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Fri 4/248:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 5/112:58 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/13$209
This CheapOair deal was found by Cheapflights users on 2/11. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Mon 6/112:58 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/11$215
This Super.com deal was found by Cheapflights users on 2/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 2/272:20 pm
SJU
-
HVN
Nonstop4h 05m
Avelo Airlines
Deal found 2/10$218
This Mytrip deal was found by Cheapflights users on 2/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 pm
HVN
-
SJU
2 stops19h 31m
Multiple Airlines
Fri 2/272:20 pm
SJU
-
HVN
Nonstop4h 05m
Multiple Airlines
Deal found 2/10$223
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 3/111:40 pm
SJU
-
HVN
Nonstop4h 05m
Avelo Airlines
Deal found 2/10$224
This CheapOair deal was found by Cheapflights users on 2/13. 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.
Wed 7/227:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 7/2911:55 am
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 2/13$225
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/288:36 pm
HVN
-
STT
1 stop15h 52m
Multiple Airlines
Tue 6/22:36 pm
STT
-
HVN
1 stop24h 21m
Multiple Airlines
Deal found 2/12$307
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/18:44 pm
HVN
-
STT
1 stop16h 47m
Multiple Airlines
Thu 3/53:36 pm
STT
-
HVN
2 stops20h 51m
Multiple Airlines
Deal found 2/13$320

Find 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 February 14, 2026.

Round-trip from

$157
(Super.com)

One-way from

$89
(CheapOair)

Popular in

December

Cheapest in

May

Average price

$299
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. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
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 February 14, 2026.
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

Fri 4/24

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/1

12:58 pm-4:50 pm

Nonstop3h 52m

$209

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/2

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 5/9

12:05 pm-3:57 pm

Nonstop3h 52m

$209

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 2/23

7:00 pm-10:47 am

1 stop14h 47m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:20 pm-5:25 pm

Nonstop4h 05m

$218

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 7/22

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 7/29

11:55 am-3:47 pm

Nonstop3h 52m

$225

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/16

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/22

12:58 pm-4:50 pm

Nonstop3h 52m

$231

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/16

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 5/23

12:05 pm-3:57 pm

Nonstop3h 52m

$231

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/2

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/6

7:00 am-2:32 pm

1 stop7h 32m

$232

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 4/15

8:50 am-12:40 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 4/22

12:05 pm-3:57 pm

Nonstop3h 52m

$232

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 5/18

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/22

12:58 pm-4:50 pm

Nonstop3h 52m

$232

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 5/18

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/27

12:05 pm-3:57 pm

Nonstop3h 52m

$240

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

Showing 1-10 of 43 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 $148). 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 February 14, 2026.

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 February 14, 2026.
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
2,898 reviews

Food

6.6

Crew

8.0

Comfort

7.5

Boarding

7.4

Entertainment

7.2

Overall

7.2

Reviews

1 / 20
4.0
Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.
JetBlue
7.2
Good
2,898 reviews
JetBlue
7.2
Good
2,898 reviews

Food

6.6

Crew

8.0

Comfort

7.5

Boarding

7.4

Entertainment

7.2

Overall

7.2

Reviews

1 / 20
4.0
Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.

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 - Oranjestad Reina Beatrix 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 $196, our data indicates the cheapest price to be $134. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $168.

  • 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 $148). 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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$101Average$250FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$176Average$285FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$421FlexibilityNo cancel feeOn-time62%

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