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$86+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Jul 7 — Jul 141
Mon 7/7
Mon 7/14
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 July 2, 2025.

Round-trip from

$169
(CheapOair)

One-way from

$86
(CheapOair)

Popular in

December

Cheapest in

March

Average price

$293

Good round-trip deal

$116 or less

Good one-way deal

$133 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. 9% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in July 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 July 2, 2025.

This CheapOair deal was found by Cheapflights users on 6/30. 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 8/248:59 pmHVN - SJU
Nonstop3h 46mAvelo Airlines
Thu 8/282:42 amSJU - HVN
Nonstop4h 03mAvelo Airlines
Deal found 6/30$169
This Trip.com deal was found by Cheapflights users on 7/1. 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.
Mon 7/214:20 pmHVN - SJU
1 stop10h 19mMultiple Airlines
Sun 7/272:42 amSJU - HVN
Nonstop4h 03mMultiple Airlines
Deal found 7/1$307
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/164:00 pmHVN - PUJ
1 stop16h 54mMultiple Airlines
Sat 8/2312:31 pmPUJ - HVN
1 stop20h 14mMultiple Airlines
Deal found 7/2$417
This Trip.com deal was found by Cheapflights users on 7/1. 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 7/184:20 pmHVN - STT
1 stop22h 50mMultiple Airlines
Sun 7/201:25 pmSTT - HVN
1 stop9h 34mMultiple Airlines
Deal found 7/1$628
This Trip.com deal was found by Cheapflights users on 6/30. 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.
Mon 7/76:40 pmHVN - AUA
2 stops39h 20mMultiple Airlines
Thu 7/105:35 pmAUA - HVN
2 stops28h 44mMultiple Airlines
Deal found 6/30$820

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 2, 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

Sun 8/24

8:59 pm-12:45 am

Nonstop3h 46m

San Juan Luis Munoz Marin Intl

Thu 8/28

2:42 am-6:45 am

Nonstop4h 03m

$169

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 7/21

4:20 pm-2:39 am

1 stop10h 19m

San Juan Luis Munoz Marin Intl

Sun 7/27

2:42 am-6:45 am

Nonstop4h 03m

$307

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Sat 8/16

4:00 pm-8:54 am

1 stop16h 54m

Punta Cana

Sat 8/23

12:31 pm-8:45 am

1 stop20h 14m

$417

New HavenSaint Thomas Island

HVN - STT

HVNSTT

Tweed-New Haven

Fri 7/18

4:20 pm-3:10 pm

1 stop22h 50m

Saint Thomas Island Cyril E King

Sun 7/20

1:25 pm-10:59 pm

1 stop9h 34m

$628

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 8/30

7:00 am-10:46 am

Nonstop3h 46m

$86

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 7/16

6:30 am-3:30 pm

1 stop9h 00m

$149

New HavenSantiago de los Caballeros

HVN - STI

HVNSTI

Tweed-New Haven

Wed 7/9

4:00 pm-12:51 pm

3 stops44h 51m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/1

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, September is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $254). Flying from New Haven to Caribbean in June is currently the most expensive (average of $339). 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 2, 2025.

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.

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 2, 2025.
Get a feel of what it's like to fly with Avelo Airlines 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
7.4
Good

Crew

8.2

Comfort

7.1

Entertainment

5.0

Overall

7.4

Boarding

7.6

Food

5.1

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
7.4
Good
Avelo Airlines
7.4
Good

Crew

8.2

Comfort

7.1

Entertainment

5.0

Overall

7.4

Boarding

7.6

Food

5.1

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.

  • 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 - Kingston Norman Manley or Tweed-New Haven - Punta Cana 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 $116. On average you can expect to pay $240. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $238.

  • 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, September is the cheapest month in which you can book a flight from New Haven to Caribbean (average of $254). Flying from New Haven to Caribbean in June is currently the most expensive (average of $339). 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 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$205FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$310FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$286FlexibilityNo cancel feeOn-timeN/A

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