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$95+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Aug 22 — Aug 291
Sat 8/22
Sat 8/29
1 adult, Economy
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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 July 23, 2026.

This Super.com deal was found by Cheapflights users on 7/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 9/307:00 pm
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 7/23$144
This Trip.com deal was found by Cheapflights users on 7/20. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 9/97:00 pm
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 7/20$154
This CheapOair deal was found by Cheapflights users on 7/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Sat 8/297:00 pm
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 7/20$156
This CheapOair deal was found by Cheapflights users on 7/20. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Fri 9/1812:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 7/20$182
This Super.com deal was found by Cheapflights users on 7/20. 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.
Sat 9/122:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Mon 9/1412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 7/20$190
This CheapOair deal was found by Cheapflights users on 7/21. 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.
Sat 10/102:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Sat 10/177:00 pm
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 7/21$192
This oojo deal was found by Cheapflights users on 7/20. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/2112:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 7/20$202
This CheapOair deal was found by Cheapflights users on 7/18. 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 9/122:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 9/1812:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 7/18$211
This CheapOair deal was found by Cheapflights users on 7/19. 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.
Wed 9/92:10 pm
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Wed 9/167:00 pm
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 7/19$213
This Kiwi.com deal was found by Cheapflights users on 7/19. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/208:36 pm
HVN
-
PUJ
1 stop23h 49m
Multiple Airlines
Wed 8/2611:39 am
PUJ
-
HVN
2 stops32h 17m
Multiple Airlines
Deal found 7/19$625
This Mytrip deal was found by Cheapflights users on 7/21. 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.
Fri 9/48:30 am
HVN
-
NAS
1 stop12h 45m
Multiple Airlines
Fri 9/117:15 am
NAS
-
HVN
1 stop15h 04m
Multiple Airlines
Deal found 7/21$659
This Mytrip deal was found by Cheapflights users on 7/18. 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 9/139:35 am
HVN
-
PUJ
2 stops26h 20m
Multiple Airlines
Sun 9/205:05 pm
PUJ
-
HVN
2 stops29h 34m
Multiple Airlines
Deal found 7/18$691

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 July 23, 2026.

Round-trip from

$144
(Super.com)

One-way from

$95
(Super.com)

Popular in

July

Cheapest in

October

Average price

$389

Good round-trip deal

$392 or less

Good one-way deal

$188 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. 12% potential increase in price ($44 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 23, 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
Quickest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 9/23

2:10 pm-6:00 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 9/30

7:00 pm-10:57 pm

Nonstop3h 57m

$211

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 9/12

2:10 pm-6:00 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 9/18

12:08 pm-4:15 pm

Nonstop4h 07m

$211

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 9/9

2:10 pm-6:00 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 9/14

12:08 pm-4:15 pm

Nonstop4h 07m

$260

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 8/15

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 8/22

7:00 pm-10:57 pm

Nonstop3h 57m

$280

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 11/13

7:00 am-11:57 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Fri 12/4

2:55 pm-6:07 pm

Nonstop4h 12m

$315

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 12/9

6:30 am-11:15 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Mon 12/14

2:55 pm-6:07 pm

Nonstop4h 12m

$321

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 8/14

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 8/19

7:00 pm-10:57 pm

Nonstop3h 57m

$339

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 8/27

8:36 pm-8:11 am

1 stop11h 35m

San Juan Luis Munoz Marin Intl

Sun 8/30

8:57 pm-6:15 pm

2 stops21h 18m

$341

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 8/19

3:42 pm-2:15 am

1 stop10h 33m

San Juan Luis Munoz Marin Intl

Tue 8/25

6:09 pm-2:57 pm

1 stop20h 48m

$347

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 8/3

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 8/19

7:00 pm-10:57 pm

Nonstop3h 57m

$352

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 44 resultsSorted by cheapest first
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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

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

Currently, October is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $196). Flying from New Haven to Caribbean in December is currently the most expensive (average of $650). 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 July 23, 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.

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 66 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.

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 July 23, 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
7.5
Good

Comfort

7.1

Overall

7.5

Entertainment

5.0

Crew

8.2

Boarding

7.7

Food

5.1

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
7.5
Good
Avelo Airlines
7.5
Good

Comfort

7.1

Overall

7.5

Entertainment

5.0

Crew

8.2

Boarding

7.7

Food

5.1

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
7.1
Good
3,020 reviews
Avelo Airlines
7.5
Good

Comfort

7.1

Overall

7.5

Entertainment

5.0

Crew

8.2

Boarding

7.7

Food

5.1

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
5.6
Fair
2,770 reviews
Avelo Airlines
7.5
Good

Comfort

7.1

Overall

7.5

Entertainment

5.0

Crew

8.2

Boarding

7.7

Food

5.1

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 50m. 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 - Nassau 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 $121. On average you can expect to pay $329. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $192.

  • 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, October is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $196). Flying from New Haven to Caribbean in December is currently the most expensive (average of $650). 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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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

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 July 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$324FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$158Average$337FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$216Average$430FlexibilityNo cancel feeOn-time62%

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