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$104+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
nov. 15 — nov. 221
sáb. 11/15
sáb. 11/22
1 adult, Economy
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Cheap 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 octubre 16, 2025.

Round-trip from

$202
(CheapOair)

One-way from

$104
(Priceline)

Popular in

December

Cheapest in

March

Average price

$220

Good round-trip deal

$363 or less

Good one-way deal

$132 or less
From Tweed-New Haven to Caribbean
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One-way flight from Tweed-New Haven to Caribbean
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Highest demand for flights based on searches. 7% potential increase in price ($21 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($11 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Tweed-New Haven to Caribbean.
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Price to beat on a one-way flight from Tweed-New Haven to Caribbean.
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Find 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 octubre 16, 2025.

This CheapOair deal was found by Cheapflights users on 10/15. 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.
sáb. 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
mié. 11/191:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/15$203
This CheapOair deal was found by Cheapflights users on 10/14. 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.
mié. 11/122:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
mar. 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/14$206
This CheapOair deal was found by Cheapflights users on 10/16. 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.
sáb. 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
dom. 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/16$211
This CheapOair deal was found by Cheapflights users on 10/15. 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.
mié. 11/122:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
jue. 11/203:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/15$217
This CheapOair deal was found by Cheapflights users on 10/15. 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.
jue. 11/208:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
dom. 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/15$218
This CheapOair deal was found by Cheapflights users on 10/16. 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.
sáb. 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
sáb. 11/221:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/16$226
This CheapOair deal was found by Cheapflights users on 10/16. 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.
sáb. 11/82:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
sáb. 11/157:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/16$233
This CheapOair deal was found by Cheapflights users on 10/13. 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.
sáb. 10/258:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
sáb. 11/87:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 10/13$243
This Mytrip deal was found by Cheapflights users on 10/15. 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.
vie. 10/318:50 amHVN - STT
2 stops25h 06mMultiple Airlines
mar. 11/41:55 pmSTT - HVN
3 stops24h 47mMultiple Airlines
Deal found 10/15$500
This Mytrip deal was found by Cheapflights users on 10/15. 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. 10/2710:30 amHVN - STT
2 stops23h 26mMultiple Airlines
lun. 11/31:55 pmSTT - HVN
1 stop9h 03mMultiple Airlines
Deal found 10/15$525
This Mytrip deal was found by Cheapflights users on 10/16. 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.
mié. 10/296:30 amHVN - PUJ
1 stop8h 30mMultiple Airlines
dom. 11/21:40 pmPUJ - HVN
2 stops20h 57mMultiple Airlines
Deal found 10/16$546
This Mytrip deal was found by Cheapflights users on 10/14. 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.
dom. 10/267:00 amHVN - AUA
2 stops33h 20mMultiple Airlines
dom. 11/24:40 pmAUA - HVN
2 stops20h 56mMultiple Airlines
Deal found 10/14$612

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 octubre 16, 2025.
Use the filters below to find and compare flights from New Haven to Caribbean that are best for you.

Fly from

New Haven

Fly to

Caribbean

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

mié. 11/12

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

mar. 11/25

3:44 am-6:45 am

Nonstop4h 01m

$206

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

jue. 11/20

8:49 pm-1:43 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

dom. 11/23

3:44 am-6:45 am

Nonstop4h 01m

$218

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 11/15

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 11/22

1:24 pm-4:25 pm

Nonstop4h 01m

$226

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

jue. 11/20

8:49 pm-1:43 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 11/22

1:24 pm-4:25 pm

Nonstop4h 01m

$243

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 11/8

2:00 pm-6:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 11/15

7:54 pm-10:55 pm

Nonstop4h 01m

$243

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

dom. 10/19

7:00 am-12:59 am

1 stop17h 59m

San Juan Luis Munoz Marin Intl

sáb. 11/1

2:41 pm-6:48 pm

Nonstop4h 07m

$247

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

vie. 12/5

2:11 pm-7:05 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

vie. 12/12

7:58 pm-10:59 pm

Nonstop4h 01m

$255

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 11/1

9:50 am-1:41 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

mié. 11/12

7:54 pm-10:55 pm

Nonstop4h 01m

$292

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

vie. 12/12

2:11 pm-7:05 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

sáb. 12/20

1:39 pm-4:40 pm

Nonstop4h 01m

$313

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

sáb. 11/29

7:30 am-12:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

vie. 12/5

7:58 pm-10:59 pm

Nonstop4h 01m

$317

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/16

Showing 1-10 of 47 results
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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, February is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $59). Flying from New Haven to Caribbean in August is currently the most expensive (average of $149). 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 octubre 16, 2025.

It’s optimal to fly from New Haven to Caribbean in the afternoon. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight at noon.

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 octubre 16, 2025.
Get a feel of what it's like to fly with Avelo Airlines, JetBlue, and Frontier 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

Crew

8.2

Comfort

7.1

Entertainment

5.0

Food

5.0

Overall

7.5

Boarding

7.7

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
7.5
Good
Avelo Airlines
7.5
Good

Crew

8.2

Comfort

7.1

Entertainment

5.0

Food

5.0

Overall

7.5

Boarding

7.7

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.
JetBlue
7.2
Good
2,907 reviews
Avelo Airlines
7.5
Good

Crew

8.2

Comfort

7.1

Entertainment

5.0

Food

5.0

Overall

7.5

Boarding

7.7

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.
Frontier
5.8
Fair
3,137 reviews
Avelo Airlines
7.5
Good

Crew

8.2

Comfort

7.1

Entertainment

5.0

Food

5.0

Overall

7.5

Boarding

7.7

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. 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 54m. 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 - Saint Thomas Island Cyril E King 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 $113. On average you can expect to pay $308. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $202.

  • 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, February is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $59). Flying from New Haven to Caribbean in August is currently the most expensive (average of $149). 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

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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 octubre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$91Average$211FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$170Average$399FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$290FlexibilityNo cancel feeOn-timeN/A

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