HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$100+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Jan 7 — Jan 141
Wed 1/7
Wed 1/14
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from New Haven to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 December 8, 2025.

This WAYA deal was found by Cheapflights users on 12/7. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/83:45 pmHVN - SJU
1 stop8h 00mMultiple Airlines
Mon 12/157:58 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 12/7$341
This Kiwi.com deal was found by Cheapflights users on 12/8. 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.
Fri 12/126:26 pmHVN - SJU
2 stops28h 50mMultiple Airlines
Mon 12/1511:38 amSJU - HVN
1 stop27h 19mMultiple Airlines
Deal found 12/8$360
This Mytrip deal was found by Cheapflights users on 12/6. 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.
Wed 12/246:20 pmHVN - SJU
2 stops26h 45mMultiple Airlines
Thu 12/253:44 amSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 12/6$365
This Mytrip deal was found by Cheapflights users on 12/8. 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 12/137:30 amHVN - SJU
1 stop15h 46mMultiple Airlines
Mon 12/157:58 pmSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 12/8$369
This Mytrip deal was found by Cheapflights users on 12/5. 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 12/258:00 amHVN - SJU
2 stops13h 05mMultiple Airlines
Sun 12/283:44 amSJU - HVN
Nonstop4h 01mMultiple Airlines
Deal found 12/5$396
This Mytrip deal was found by Cheapflights users on 12/7. 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 12/316:20 pmHVN - SJU
2 stops26h 45mMultiple Airlines
Thu 2/267:49 pmSJU - HVN
2 stops20h 16mMultiple Airlines
Deal found 12/7$405
This Kiwi.com deal was found by Cheapflights users on 12/7. 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.
Tue 12/232:42 pmHVN - PUJ
2 stops22h 47mMultiple Airlines
Sat 12/273:08 pmPUJ - HVN
1 stop28h 38mMultiple Airlines
Deal found 12/7$696
This Mytrip deal was found by Cheapflights users on 12/8. 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 12/246:20 pmHVN - PUJ
2 stops21h 30mMultiple Airlines
Mon 12/296:08 pmPUJ - HVN
2 stops20h 37mMultiple Airlines
Deal found 12/8$738
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/257:26 pmHVN - PUJ
1 stop23h 59mMultiple Airlines
Mon 12/296:08 pmPUJ - HVN
2 stops20h 49mMultiple Airlines
Deal found 12/8$875
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/257:26 pmHVN - PUJ
1 stop23h 59mMultiple Airlines
Tue 12/3011:37 amPUJ - HVN
2 stops27h 24mMultiple Airlines
Deal found 12/8$966
This Mytrip deal was found by Cheapflights users on 12/8. 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 12/246:20 pmHVN - STI
3 stops31h 22mMultiple Airlines
Sun 12/283:43 amSTI - HVN
2 stops19h 46mMultiple Airlines
Deal found 12/8$980

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 December 8, 2025.

Round-trip from

$223
(Super.com)

One-way from

$100
(Super.com)

Popular in

December

Cheapest in

March

Average price

$365

Good round-trip deal

$268 or less

Good one-way deal

$122 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. 8% potential increase in price ($23 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Tweed-New Haven to Caribbean.
Search Deals
Price to beat on a one-way 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 December 8, 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

Mon 1/26

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:54 pm-10:59 pm

Nonstop4h 05m

$200

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 1/26

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:54 pm-10:59 pm

Nonstop4h 05m

$223

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 1/8

2:26 pm-12:47 pm

2 stops21h 21m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-7:04 pm

1 stop14h 04m

$266

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/30

12:07 pm-5:00 pm

2 stops27h 53m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:00 am-2:01 pm

1 stop9h 01m

$267

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 1/29

2:26 pm-11:45 am

2 stops20h 19m

San Juan Luis Munoz Marin Intl

Tue 2/3

6:00 am-2:01 pm

1 stop9h 01m

$277

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 2/5

8:44 pm-9:47 am

1 stop12h 03m

San Juan Luis Munoz Marin Intl

Mon 2/9

8:00 am-2:01 pm

1 stop31h 01m

$278

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 3/1

8:59 pm-1:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 3/7

12:30 pm-3:35 pm

Nonstop4h 05m

$279

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Tue 1/20

2:46 pm-11:33 pm

1 stop7h 47m

San Juan Luis Munoz Marin Intl

Mon 1/26

8:05 pm-2:01 pm

1 stop18h 56m

$284

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 2/4

3:33 pm-1:41 am

2 stops33h 08m

San Juan Luis Munoz Marin Intl

Mon 2/9

8:05 pm-2:01 pm

1 stop18h 56m

$291

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 2/6

12:07 pm-11:33 pm

2 stops10h 26m

San Juan Luis Munoz Marin Intl

Mon 2/9

8:00 am-2:01 pm

1 stop31h 01m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 31 results
1
2
3
4

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 December 8, 2025.

It’s optimal to fly from New Haven to Caribbean in the afternoon. By choosing this option you can save up to 41% 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 December 8, 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
7.6
Good

Boarding

7.8

Comfort

7.1

Food

5.0

Crew

8.3

Overall

7.6

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
7.6
Good
Avelo Airlines
7.6
Good

Boarding

7.8

Comfort

7.1

Food

5.0

Crew

8.3

Overall

7.6

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
2,896 reviews
Avelo Airlines
7.6
Good

Boarding

7.8

Comfort

7.1

Food

5.0

Crew

8.3

Overall

7.6

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
3,087 reviews
Avelo Airlines
7.6
Good

Boarding

7.8

Comfort

7.1

Food

5.0

Crew

8.3

Overall

7.6

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 58m. 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 - Saint Thomas Island Cyril E King 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 $99. On average you can expect to pay $297. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $279.

  • 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for New Haven to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Miami flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Fort Lauderdale flights
LaGuardia to Miami flights
Newark to Cancún flights
Newark to Miami flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Orlando flights
Newark to West Palm Beach flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Heathrow flights
Newark to Las Vegas flights
Newark to Los Angeles flights
LaGuardia to Dallas/Fort Worth flights
Newark to Dallas/Fort Worth flights
Newark to Orlando flights
Newark to Mexico City flights
John F Kennedy Intl to Santo Domingo flights
Newark to Heathrow flights
John F Kennedy Intl to Mexico City flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Atlanta flights
John F Kennedy Intl to Haneda flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Cancún flights
LaGuardia to Orlando flights
John F Kennedy Intl to Hobby flights
Newark to Charles de Gaulle flights
LaGuardia to Tampa flights
John F Kennedy Intl to Sky Harbor Intl flights
Newark to Haneda flights
LaGuardia to Atlanta flights
John F Kennedy Intl to Tampa flights
Newark to Narita flights
LaGuardia to Los Angeles flights
LaGuardia to Hobby flights
Newark to San Francisco flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
John F Kennedy Intl to New Orleans flights
Newark to Santo Domingo flights
LaGuardia to West Palm Beach flights
Newark to Hobby flights
LaGuardia to Luis Munoz Marin Intl flights
LaGuardia to Las Vegas flights

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 December 8, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$216FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$186Average$464FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$197Average$293FlexibilityNo cancel feeOn-timeN/A

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.