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$111+ 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 9/21. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Jun 26 — Jul 31
Fri 6/26
Fri 7/3
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 May 27, 2026.

This Trip.com deal was found by Cheapflights users on 5/27. 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 9/187:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/2112:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/27$221
This Trip.com deal was found by Cheapflights users on 5/26. 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 9/47:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/712:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/26$243
This Super.com deal was found by Cheapflights users on 5/25. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/2812:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/25$251
This CheapOair deal was found by Cheapflights users on 5/25. 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.
Mon 9/77:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/1412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/25$266
This CheapOair deal was found by Cheapflights users on 5/26. 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 5/26$275
This CheapOair deal was found by Cheapflights users on 5/26. 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 8/246:30 am
HVN
-
SJU
Nonstop3h 50m
Avelo Airlines
Fri 8/2811:30 am
SJU
-
HVN
Nonstop3h 57m
Avelo Airlines
Deal found 5/26$276
This CheapOair deal was found by Cheapflights users on 5/23. 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.
Fri 9/117:00 am
HVN
-
SJU
Nonstop3h 57m
Avelo Airlines
Mon 9/1412:08 pm
SJU
-
HVN
Nonstop4h 07m
Avelo Airlines
Deal found 5/23$292
This Mytrip deal was found by Cheapflights users on 5/23. 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.
Sun 10/189:20 am
HVN
-
NAS
1 stop7h 05m
Multiple Airlines
Sat 10/2412:00 pm
NAS
-
HVN
1 stop8h 44m
Multiple Airlines
Deal found 5/23$571
This Trip.com deal was found by Cheapflights users on 5/27. 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.
Thu 7/98:13 pm
HVN
-
PUJ
2 stops39h 41m
Multiple Airlines
Tue 7/1411:50 am
PUJ
-
HVN
2 stops22h 05m
Multiple Airlines
Deal found 5/27$577
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:42 pm
HVN
-
PUJ
1 stop27h 08m
Multiple Airlines
Sat 6/209:29 pm
PUJ
-
HVN
2 stops22h 27m
Multiple Airlines
Deal found 5/24$603
This Mytrip deal was found by Cheapflights users on 5/24. 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 7/86:30 am
HVN
-
NAS
1 stop8h 15m
Multiple Airlines
Wed 7/157:15 am
NAS
-
HVN
1 stop6h 19m
Multiple Airlines
Deal found 5/24$604
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/133:42 pm
HVN
-
PUJ
1 stop27h 08m
Multiple Airlines
Fri 6/191:10 pm
PUJ
-
HVN
1 stop25h 47m
Multiple Airlines
Deal found 5/24$612

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 May 27, 2026.

Round-trip from

$243
(Trip.com)

One-way from

$112
(CheapOair)

Popular in

April

Cheapest in

October

Average price

$350

Good round-trip deal

$382 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 ($42 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 May 2026
Search Deals
Price to beat on a round-trip 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 May 27, 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

Fri 9/4

7:00 am-10:57 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Mon 9/7

12:08 pm-4:15 pm

Nonstop4h 07m

$289
Quickest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 6/8

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 6/12

12:58 pm-4:50 pm

Nonstop3h 52m

$323

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 8/17

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 8/31

11:30 am-3:27 pm

Nonstop3h 57m

$344

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 9/3

6:31 pm-3:58 pm

2 stops21h 27m

San Juan Luis Munoz Marin Intl

Mon 9/7

12:08 pm-4:15 pm

Nonstop4h 07m

$375

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 8/23

6:31 pm-2:29 pm

1 stop19h 58m

San Juan Luis Munoz Marin Intl

Thu 8/27

6:00 am-4:47 pm

2 stops10h 47m

$379

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 7/4

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 7/6

1:03 pm-4:55 pm

Nonstop3h 52m

$393

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 6/12

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 6/17

12:10 pm-4:02 pm

Nonstop3h 52m

$400

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 7/4

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 7/24

1:03 pm-4:55 pm

Nonstop3h 52m

$414

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 8/7

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 8/10

1:03 pm-4:55 pm

Nonstop3h 52m

$423

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 8/27

8:36 pm-8:09 am

1 stop11h 33m

San Juan Luis Munoz Marin Intl

Mon 8/31

6:16 pm-2:02 pm

1 stop19h 46m

$427

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/26

Showing 1-10 of 41 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, 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 $260). 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 May 27, 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 49 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 May 27, 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

Boarding

7.7

Crew

8.3

Entertainment

5.0

Overall

7.6

Food

5.1

Comfort

7.1

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
7.6
Good
Avelo Airlines
7.6
Good

Boarding

7.7

Crew

8.3

Entertainment

5.0

Overall

7.6

Food

5.1

Comfort

7.1

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
2,982 reviews
Avelo Airlines
7.6
Good

Boarding

7.7

Crew

8.3

Entertainment

5.0

Overall

7.6

Food

5.1

Comfort

7.1

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
2,931 reviews
Avelo Airlines
7.6
Good

Boarding

7.7

Crew

8.3

Entertainment

5.0

Overall

7.6

Food

5.1

Comfort

7.1

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 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 $168. On average you can expect to pay $398. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $243.

  • 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 $260). 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

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 May 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$302FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$155Average$314FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$207Average$424FlexibilityNo cancel feeOn-time62%

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