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$106+ 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 11/20. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Dec 6 — Dec 131
Sat 12/6
Sat 12/13
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 November 6, 2025.

Round-trip from

$222
(CheapOair)

One-way from

$106
(eDestinos)

Popular in

December

Cheapest in

March

Average price

$266

Good round-trip deal

$208 or less

Good one-way deal

$161 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. 6% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 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 November 6, 2025.

This CheapOair deal was found by Cheapflights users on 11/5. 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 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/5$215
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Wed 11/191:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/6$219
This Mytrip deal was found by Cheapflights users on 11/5. 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.
Thu 11/208:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/5$227
This Mytrip deal was found by Cheapflights users on 11/5. 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.
Thu 11/206:30 amHVN - SJU
1 stop16h 54mMultiple Airlines
Sun 11/233:44 amSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 11/5$260
This CheapOair deal was found by Cheapflights users on 11/6. 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 11/197:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
Tue 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/6$271
This CheapOair deal was found by Cheapflights users on 11/6. 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.
Sun 11/308:49 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Fri 12/57:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/6$279
This Kiwi.com deal was found by Cheapflights users on 11/4. 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 12/42:28 pmHVN - SJU
1 stop22h 08mMultiple Airlines
Thu 12/1110:42 amSJU - HVN
2 stops32h 04mMultiple Airlines
Deal found 11/4$304
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mMultiple Airlines
Wed 11/193:44 pmSJU - HVN
3 stops22h 41mMultiple Airlines
Deal found 11/6$315
This CheapOair deal was found by Cheapflights users on 11/4. 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 12/52:11 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Mon 12/87:58 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Deal found 11/4$317
This Kiwi.com deal was found by Cheapflights users on 11/5. 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 11/207:26 pmHVN - STT
1 stop18h 04mMultiple Airlines
Mon 11/242:00 pmSTT - HVN
2 stops22h 57mMultiple Airlines
Deal found 11/5$461
This Mytrip deal was found by Cheapflights users on 11/5. 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 12/71:50 pmHVN - GCM
2 stops21h 45mMultiple Airlines
Sat 12/135:56 pmGCM - HVN
2 stops19h 21mMultiple Airlines
Deal found 11/5$480
This Trip.com deal was found by Cheapflights users on 11/5. 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 12/57:30 amHVN - NAS
1 stop11h 45mMultiple Airlines
Tue 12/911:30 amNAS - HVN
1 stop25h 49mMultiple Airlines
Deal found 11/5$507

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 November 6, 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

Thu 11/20

8:49 pm-1:43 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 11/23

3:44 am-6:45 am

Nonstop4h 01m

$227

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 11/19

7:30 am-12:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Tue 11/25

3:44 am-6:45 am

Nonstop4h 01m

$271

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/30

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Mon 2/2

7:54 pm-10:59 pm

Nonstop4h 05m

$276

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 11/30

8:49 pm-1:43 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Fri 12/5

7:58 pm-10:59 pm

Nonstop4h 01m

$279

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 11/29

7:30 am-12:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Fri 12/5

7:58 pm-10:59 pm

Nonstop4h 01m

$336

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 12/31

6:20 pm-10:05 pm

2 stops26h 45m

San Juan Luis Munoz Marin Intl

Thu 1/8

6:00 am-2:33 pm

1 stop9h 33m

$340

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 12/31

6:20 pm-10:05 pm

2 stops26h 45m

San Juan Luis Munoz Marin Intl

Fri 1/9

6:00 am-10:39 pm

1 stop17h 39m

$340

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/9

12:07 pm-12:59 pm

2 stops23h 52m

San Juan Luis Munoz Marin Intl

Mon 1/12

9:37 pm-2:01 pm

1 stop17h 24m

$346

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 12/4

2:28 pm-1:36 pm

1 stop22h 08m

San Juan Luis Munoz Marin Intl

Thu 12/11

11:38 am-6:46 pm

1 stop8h 08m

$363

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/30

12:07 pm-2:50 am

2 stops13h 43m

San Juan Luis Munoz Marin Intl

Mon 2/2

11:05 am-2:01 pm

1 stop27h 56m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

Showing 1-10 of 32 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 November 6, 2025.

It’s optimal to fly from New Haven to Caribbean in the afternoon. By choosing this option you can save up to 46% 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 November 6, 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

Overall

7.5

Food

5.0

Crew

8.2

Boarding

7.7

Comfort

7.1

Entertainment

5.0

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

Overall

7.5

Food

5.0

Crew

8.2

Boarding

7.7

Comfort

7.1

Entertainment

5.0

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

Overall

7.5

Food

5.0

Crew

8.2

Boarding

7.7

Comfort

7.1

Entertainment

5.0

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
3,115 reviews
Avelo Airlines
7.5
Good

Overall

7.5

Food

5.0

Crew

8.2

Boarding

7.7

Comfort

7.1

Entertainment

5.0

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 - Nassau Intl or Tweed-New Haven - Castries Hewanorra 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 $112. On average you can expect to pay $222. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $278.

  • 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 November 6, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$211FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$464FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$286FlexibilityNo cancel feeOn-timeN/A

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