HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$133+ Cheap flights from New Haven (HVN) to Caribbean

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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
mai 24 — mai 311
dim. 5/24
dim. 5/31
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from New Haven to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from New Haven to Caribbean

Cheapest flights from New Haven to Caribbean
Explore the most affordable flight options available from New Haven to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on avril 24, 2026.

This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/316:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
lun. 9/1411:38 am
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 4/20$223
This Mytrip deal was found by Cheapflights users on 4/19. 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. 5/411:50 am
HVN
-
SJU
1 stop12h 04m
Multiple Airlines
jeu. 5/72:09 am
SJU
-
HVN
1 stop13h 06m
Multiple Airlines
Deal found 4/19$240
This CheapOair deal was found by Cheapflights users on 4/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 8/316:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
lun. 9/711:38 am
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 4/21$245
This CheapOair deal was found by Cheapflights users on 4/22. 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.
ven. 9/116:30 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
ven. 9/1811:38 am
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 4/22$255
This CheapOair deal was found by Cheapflights users on 4/22. 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.
lun. 9/76:30 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
ven. 9/1111:38 am
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 4/22$258
This CheapOair deal was found by Cheapflights users on 4/19. 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.
ven. 9/256:30 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
lun. 9/2811:38 am
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 4/19$261
This CheapOair deal was found by Cheapflights users on 4/19. 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. 5/258:00 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
ven. 5/2912:58 pm
SJU
-
HVN
Nonstop3h 52m
Avelo Airlines
Deal found 4/19$277
This Mytrip deal was found by Cheapflights users on 4/23. 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.
dim. 6/146:30 pm
HVN
-
NAS
2 stops24h 45m
Multiple Airlines
ven. 6/1911:30 am
NAS
-
HVN
1 stop10h 26m
Multiple Airlines
Deal found 4/23$569
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/133:42 pm
HVN
-
PUJ
1 stop27h 08m
Multiple Airlines
ven. 6/191:10 pm
PUJ
-
HVN
1 stop25h 47m
Multiple Airlines
Deal found 4/22$578
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jeu. 5/78:36 pm
HVN
-
STT
1 stop17h 40m
Multiple Airlines
lun. 5/113:21 pm
STT
-
HVN
1 stop22h 41m
Multiple Airlines
Deal found 4/22$592
This Mytrip deal was found by Cheapflights users on 4/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/67:00 am
HVN
-
PUJ
1 stop15h 01m
Multiple Airlines
sam. 6/137:10 pm
PUJ
-
HVN
2 stops22h 32m
Multiple Airlines
Deal found 4/21$614
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 6/133:42 pm
HVN
-
PUJ
1 stop27h 08m
Multiple Airlines
sam. 6/209:29 pm
PUJ
-
HVN
2 stops20h 17m
Multiple Airlines
Deal found 4/22$615

Find flight deals from New Haven to Caribbean

Keep the following information in mind while searching for New Haven to Caribbean flight deals. Data was last updated avril 24, 2026.

Round-trip from

$223
(Super.com)

One-way from

$133
(CheapOair)

Popular in

December

Cheapest in

October

Average price

$346

Good round-trip deal

$258 or less

Good one-way deal

$124 or less
From Tweed-New Haven to Caribbean
Search Deals
One-way flight from Tweed-New Haven to Caribbean
Search Deals
Highest demand for flights based on searches. 2% potential increase in price ($7 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals
Price to beat on a round-trip flight from Tweed-New Haven to Caribbean.
Search Deals
Price to beat on a one-way flight from Tweed-New Haven to Caribbean.
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from New Haven to Caribbean 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 avril 24, 2026.
Use the filters below to find and compare flights from New Haven to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

lun. 9/7

6:30 am-10:27 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

ven. 9/11

11:38 am-3:45 pm

Nonstop4h 07m

$258

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

ven. 9/11

6:30 am-10:27 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

ven. 9/18

11:38 am-3:45 pm

Nonstop4h 07m

$287
Quickest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

lun. 5/18

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

sam. 5/23

12:05 pm-3:57 pm

Nonstop3h 52m

$304

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

ven. 8/21

6:30 am-10:20 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

lun. 8/24

11:30 am-3:27 pm

Nonstop3h 57m

$320

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mer. 6/10

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

sam. 6/20

12:10 pm-4:02 pm

Nonstop3h 52m

$320

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

lun. 5/4

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

ven. 5/8

12:58 pm-4:50 pm

Nonstop3h 52m

$340

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sam. 5/23

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

jeu. 5/28

2:09 am-3:15 pm

1 stop13h 06m

$359

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

ven. 9/18

6:30 am-10:27 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

lun. 9/21

11:38 am-3:45 pm

Nonstop4h 07m

$360

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sam. 8/15

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

lun. 8/17

1:03 pm-4:55 pm

Nonstop3h 52m

$378

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sam. 7/4

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

sam. 7/11

12:10 pm-4:02 pm

Nonstop3h 52m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/21

Showing 1-10 of 46 resultsSorted by cheapest first
1
2
3
...
5

Best time to book a flight from New Haven to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

How far ahead should I book a flight from New Haven to Caribbean?

The best time to book flights from New Haven to Caribbean is 47 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, March is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $78). Flying from New Haven to Caribbean in September is currently the most expensive (average of $270). 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 CB?

Find hourly flight availability from New Haven to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated avril 24, 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 as you normally would.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated avril 24, 2026.
Get a feel of what it's like to fly with Avelo Airlines,JetBlue, andFrontier from New Haven to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Avelo Airlines
7.6
Good

Crew

8.3

Boarding

7.7

Comfort

7.1

Overall

7.6

Food

5.1

Entertainment

5.0

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
Avelo Airlines
7.6
Good
Avelo Airlines
7.6
Good

Crew

8.3

Boarding

7.7

Comfort

7.1

Overall

7.6

Food

5.1

Entertainment

5.0

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
JetBlue
7.2
Good
2,954 reviews
Avelo Airlines
7.6
Good

Crew

8.3

Boarding

7.7

Comfort

7.1

Overall

7.6

Food

5.1

Entertainment

5.0

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.
Frontier
5.7
Fair
2,980 reviews
Avelo Airlines
7.6
Good

Crew

8.3

Boarding

7.7

Comfort

7.1

Overall

7.6

Food

5.1

Entertainment

5.0

Reviews

1 / 7
8.0
Excellent

Anonymous,Dec 2025

USA - ROC

The Customer Service department, particularly the baggage claim process, needs significant improvement. Currently, this department is only accessible via email, which makes resolving urgent issues difficult and frustrating. On December 8th, while traveling from Rochester, NY to Concord, NC, my elderly parent’s walker was never boarded onto the aircraft. This caused considerable frustration, stress, and disappointment during our travel. A mobility aid such as a walker is not optional—it is essential for my parent’s safety and independence. The failure to properly handle this item created a serious and avoidable issue. This situation significantly impacted our travel experience and highlights the need for better communication, accountability, and handling of mobility assistance devices. I hope this matter is taken seriously and that improvements are made to prevent similar incidents in the future.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Caribbean. 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?

    Located just 3.6 mi from the city center, Tweed-New Haven (HVN) is the airport most travelers will use when flying to Caribbean from New Haven.

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

    Airlines like Avelo Airlines fly from New Haven to Caribbean in about 3h 57m. The time it takes to get you to your destination is usually consistent. There are 1628 mi between New Haven and Caribbean. Most flights are nonstop.

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

    Most travelers choose Tweed-New Haven - San Juan Luis Munoz Marin Intl, Tweed-New Haven - Punta Cana or Tweed-New Haven - Montego Bay Sangster Intl when deciding on the best route from New Haven to Caribbean.

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

    The cheapest flight price from New Haven to Caribbean is $118. On average you can expect to pay $263. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $245.

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

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

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

    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.

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

    Yes. Cheapflights offers flight deals from New Haven to Caribbean 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?

    Currently, March is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $78). Flying from New Haven to Caribbean in September is currently the most expensive (average of $270). 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

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to San Francisco flights
Newark to San Francisco flights
LaGuardia to San Francisco flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
LaGuardia to Miami flights
LaGuardia to Dallas/Fort Worth flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Miami flights
Newark to Dallas/Fort Worth flights
Newark to Los Angeles flights
Newark to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
John F Kennedy Intl to Heathrow flights
Newark to O'Hare Intl flights
Newark to Heathrow flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
Newark to Orlando flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Las Vegas flights
LaGuardia to Atlanta flights
LaGuardia to Orlando flights
Newark to Charles de Gaulle flights
LaGuardia to O'Hare Intl flights
Newark to Seattle flights
LaGuardia to Los Angeles flights
Newark to Cancún flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
LaGuardia to Hobby flights
LaGuardia to Las Vegas flights
Newark to Tampa flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Hobby flights
LaGuardia to Tampa flights
Newark to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Haneda flights
John F Kennedy Intl to Mexico City flights
Newark to Mexico City flights
John F Kennedy Intl to Seattle flights
Newark to Haneda flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
LaGuardia to Heathrow flights
Newark to Atlanta flights
Newark to West Palm Beach flights

Top 3 airlines flying from New Haven to Caribbean

Discover the top 3 airlines that operate flights from New Haven to Caribbean. 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 avril 24, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$135Average$324FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$163Average$311FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$207Average$414FlexibilityNo cancel feeOn-time62%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.