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$103+ Cheap flights from Caribbean to New Haven (HVN)

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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — HVN
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
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Cheap flight deals from Caribbean to New Haven

Keep the following information in mind while searching for Caribbean to New Haven flight deals. Data was last updated October 16, 2025.

Round-trip from

$202
(OneTravel)

One-way from

$103
(OneTravel)

Popular in

August

Cheapest in

February

Average price

$206

Good round-trip deal

$161 or less

Good one-way deal

$128 or less
From Caribbean to Tweed-New Haven
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One-way flight from Caribbean to Tweed-New Haven
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Highest demand for flights based on searches. 10% potential increase in price ($25 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($6 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 Caribbean to Tweed-New Haven.
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Price to beat on a one-way flight from Caribbean to Tweed-New Haven.
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Find flight deals from Caribbean to New Haven

Cheapest flights from Caribbean to New Haven
Explore the most affordable flight options available from Caribbean to New Haven. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/127:54 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Sat 11/152:00 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Deal found 10/14$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.
Sun 12/213:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Thu 1/18:59 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Deal found 10/16$244
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.
Wed 12/241:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Thu 1/18:59 pmHVN - SJU
Nonstop3h 54mAvelo Airlines
Deal found 10/14$258
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.
Wed 11/191:24 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Sat 11/221:10 pmHVN - SJU
2 stops20h 39mMultiple Airlines
Deal found 10/16$260
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.
Thu 12/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Sat 1/106:30 amHVN - SJU
Nonstop3h 58mAvelo Airlines
Deal found 10/13$285
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.
Tue 11/253:44 amSJU - HVN
Nonstop4h 01mAvelo Airlines
Sat 11/297:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
Deal found 10/15$287
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/191:24 pmSJU - HVN
Nonstop4h 01mAvelo Airlines
Sat 11/227:30 amHVN - SJU
Nonstop3h 54mAvelo Airlines
Deal found 10/16$298
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/221:41 pmSJU - HVN
Nonstop4h 07mAvelo Airlines
Sat 10/258:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
Deal found 10/15$300
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/221:41 pmSJU - HVN
Nonstop4h 07mAvelo Airlines
Wed 10/298:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
Deal found 10/15$305
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.
Thu 11/63:37 pmSJU - HVN
2 stops22h 05mMultiple Airlines
Wed 11/122:00 pmHVN - SJU
Nonstop3h 54mMultiple Airlines
Deal found 10/14$316
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/181:41 pmSJU - HVN
Nonstop4h 07mAvelo Airlines
Sat 10/258:50 amHVN - SJU
Nonstop3h 51mAvelo Airlines
Deal found 10/15$317
This Trip.com 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/153:30 pmSDQ - HVN
1 stop8h 25mMultiple Airlines
Sat 11/227:30 amHVN - SDQ
1 stop10h 48mMultiple Airlines
Deal found 10/16$495

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to New Haven 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 October 16, 2025.
Use the filters below to find and compare flights from Caribbean to New Haven that are best for you.

Fly from

Caribbean

Fly to

New Haven

Route

Depart

Return

Price

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Wed 11/12

7:54 pm-10:55 pm

Nonstop4h 01m

Tweed-New Haven

Sat 11/15

2:00 pm-6:54 pm

Nonstop3h 54m

$218

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Thu 12/25

3:44 am-6:45 am

Nonstop4h 01m

Tweed-New Haven

Sat 1/10

6:30 am-11:28 am

Nonstop3h 58m

$285

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Tue 11/25

3:44 am-6:45 am

Nonstop4h 01m

Tweed-New Haven

Sat 11/29

7:30 am-12:24 pm

Nonstop3h 54m

$287

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Wed 11/19

1:24 pm-4:25 pm

Nonstop4h 01m

Tweed-New Haven

Sat 11/22

7:30 am-12:24 pm

Nonstop3h 54m

$298

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Wed 10/22

1:41 pm-5:48 pm

Nonstop4h 07m

Tweed-New Haven

Sat 10/25

8:50 am-12:41 pm

Nonstop3h 51m

$300

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Wed 10/22

1:41 pm-5:48 pm

Nonstop4h 07m

Tweed-New Haven

Wed 10/29

8:50 am-12:41 pm

Nonstop3h 51m

$305

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Thu 11/6

3:37 pm-12:42 pm

2 stops22h 05m

Tweed-New Haven

Wed 11/12

2:00 pm-6:54 pm

Nonstop3h 54m

$316

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Sat 10/25

1:41 pm-5:48 pm

Nonstop4h 07m

Tweed-New Haven

Sat 11/1

9:50 am-1:41 pm

Nonstop3h 51m

$320

San JuanNew Haven

SJU - HVN

SJUHVN

San Juan Luis Munoz Marin Intl

Tue 11/25

3:44 am-6:45 am

Nonstop4h 01m

Tweed-New Haven

Sun 11/30

8:49 pm-1:43 am

Nonstop3h 54m

$323

Santo DomingoNew Haven

SDQ - HVN

SDQHVN

Santo Domingo Las Americas

Sat 11/15

3:30 pm-10:55 pm

1 stop8h 25m

Tweed-New Haven

Sat 11/22

7:30 am-7:18 pm

1 stop10h 48m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Showing 1-10 of 21 results
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Best time to book a flight from Caribbean to New Haven

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean to New Haven (average of $79). Flying from Caribbean to New Haven in September is currently the most expensive (average of $113). 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 CB to HVN?

Find hourly flight availability from Caribbean to New Haven. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 16, 2025.

One of the essential ways to save on airfare from Caribbean to New Haven is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the afternoon could potentially save you up to 68% on airfare.

Reviews of airlines servicing New Haven

Get insights into the airlines that provide service to New Haven. 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 New Haven. Reviews last updated October 16, 2025.
Read through reviews of airlines operating flights from Caribbean to New Haven, such as Avelo Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Avelo Airlines
7.5
Good

Comfort

7.1

Entertainment

5.0

Overall

7.5

Boarding

7.7

Food

5.0

Crew

8.2

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

Comfort

7.1

Entertainment

5.0

Overall

7.5

Boarding

7.7

Food

5.0

Crew

8.2

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 Caribbean to New Haven. 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 into for flights to New Haven from Caribbean?

    Tweed-New Haven (HVN) is the airport you will fly into if you book a flight from Caribbean to New Haven. It is only a 3.6 mi journey from Tweed-New Haven (HVN) to New Haven’s city center.

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

    Avelo Airlines can get you from Caribbean to New Haven in just under 4h 01m. Your travel time will be generally consistent. Airlines will cover a distance of 1628 mi. Generally, flights for this route are nonstop.

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

    The most popular route from Caribbean to New Haven is San Juan Luis Munoz Marin Intl - Tweed-New Haven. You may also consider Port of Spain Piarco Intl - Tweed-New Haven or George Town Owen Roberts Intl - Tweed-New Haven.

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

    On average you can expect to pay $199 for a flight from Caribbean to New Haven. The cheapest flight overall is $83 while the most popular route, (San Juan Luis Munoz Marin Intl - Tweed-New Haven) is currently priced at $203.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to New Haven.

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

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

    Currently, April is the cheapest month in which you can book a flight from Caribbean to New Haven (average of $79). Flying from Caribbean to New Haven in September is currently the most expensive (average of $113). 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

Traveling to a place near New Haven?

Book flights to New Haven if you plan to visit one of these locations
Wallingford

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Top airline flying from Caribbean to New Haven

Discover the top airline that operate flights from Caribbean to New Haven. 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Avelo AirlinesCheapest$156Average$257FlexibilityNo cancel feeOn-timeN/A

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