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

There are many flights that can get you from New Haven to Caribbean Islands in 3h 58m. Fly via Avelo Airlines to get the fastest option. Airlines will cover a distance of 1628 mi. All flights are typically nonstop.

In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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

Most travelers choose Tweed-New Haven - San Juan Luis Munoz Marin Intl, Tweed-New Haven - Punta Cana or Tweed-New Haven - Castries Hewanorra when deciding on the best route from New Haven to Caribbean Islands.

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

Looking for the cheapest flight from New Haven to Caribbean Islands? While on average our users pay $285, our data indicates the cheapest price to be $211. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $214.

What airport do you fly from for flights from New Haven to Caribbean Islands?

Most people fly from Tweed-New Haven (HVN) if they book a flight from New Haven to Caribbean Islands. Tweed-New Haven is conveniently located just 3.6 mi from New Haven’s city center.

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

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

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

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 Islands.

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

Yes. Cheapflights offers flight deals from New Haven to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

$93+ Flights from New Haven to Caribbean Islands

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from New Haven to Caribbean Islands 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 Islands

Cheapest flights from New Haven to Caribbean Islands
Explore the most affordable flight options available from New Haven to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.

Tue 12/302:42 pmHVN - SJU

1 stop30h 24mMultiple Airlines

Tue 1/611:45 amSJU - HVN

2 stops28h 03mMultiple Airlines

Deal found 12/29

$786

Tue 12/304:05 pmHVN - SJU

2 stops18h 53mMultiple Airlines

Wed 1/1412:28 pmSJU - HVN

Nonstop4h 05mMultiple Airlines

Deal found 12/30

$835

Wed 12/311:30 pmHVN - SJU

1 stop7h 35mMultiple Airlines

Sat 1/31:39 pmSJU - HVN

Nonstop4h 01mMultiple Airlines

Deal found 12/30

$838

Best flights from New Haven to Caribbean Islands
Discover carefully curated flight deals from New Haven to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 31, 2025.

Sun 3/228:59 pmHVN - SJU

Nonstop3h 50mAvelo Airlines

Sat 3/2811:30 amSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/30

$201

Wed 1/216:30 amHVN - SJU

Nonstop3h 58mMultiple Airlines

Wed 1/286:00 amSJU - HVN

1 stop9h 23mMultiple Airlines

Deal found 12/31

$212

Mon 1/121:55 pmHVN - SJU

Nonstop3h 58mMultiple Airlines

Fri 1/162:41 pmSJU - HVN

1 stop8h 38mMultiple Airlines

Deal found 12/29

$214

Wed 1/146:30 amHVN - SJU

Nonstop3h 58mAvelo Airlines

Fri 1/307:54 pmSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/30

$215

Wed 1/288:00 amHVN - SJU

1 stop14h 33mMultiple Airlines

Wed 2/46:00 amSJU - HVN

1 stop9h 23mMultiple Airlines

Deal found 12/31

$257

Sun 4/58:59 pmHVN - SJU

Nonstop3h 50mAvelo Airlines

Wed 4/811:30 amSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/30

$274

Wed 1/216:30 amHVN - SJU

Nonstop3h 58mMultiple Airlines

Sat 1/248:00 amSJU - HVN

1 stop7h 23mMultiple Airlines

Deal found 12/30

$270

Thu 1/152:26 pmHVN - SJU

1 stop9h 45mMultiple Airlines

Wed 1/217:00 pmSJU - HVN

2 stops41h 27mMultiple Airlines

Deal found 12/29

$279

Tue 3/102:46 pmHVN - SJU

1 stop18h 08mMultiple Airlines

Thu 3/1912:04 pmSJU - HVN

1 stop8h 00mMultiple Airlines

Deal found 12/28

$284

Fri 3/2012:07 pmHVN - PUJ

1 stop22h 23mBreeze Airways

Wed 3/2511:30 amPUJ - HVN

3 stops50h 42mBreeze Airways

Deal found 12/30

$973

Sat 2/142:45 pmHVN - PUJ

3 stops22h 15mMultiple Airlines

Sat 2/215:47 amPUJ - HVN

1 stop9h 47mMultiple Airlines

Deal found 12/30

$467

Fri 2/133:25 pmHVN - STI

2 stops23h 10mMultiple Airlines

Fri 2/204:40 pmSTI - HVN

2 stops22h 54mMultiple Airlines

Deal found 12/30

$468

Fri 3/2012:07 pmHVN - PUJ

1 stop22h 23mMultiple Airlines

Wed 3/2511:30 amPUJ - HVN

2 stops32h 34mMultiple Airlines

Deal found 12/30

$481

Sun 3/17:00 amHVN - PUJ

1 stop8h 36mMultiple Airlines

Sun 3/86:00 pmPUJ - HVN

2 stops27h 00mMultiple Airlines

Deal found 12/29

$502

Last-minute flights from New Haven to Caribbean Islands
Discover last-minute flight deals from New Haven to Caribbean Islands. Data last updated December 31, 2025 and is based on user searches.

Fri 1/23:05 pmHVN - STI

2 stops10h 37mMultiple Airlines

Sun 1/114:40 pmSTI - HVN

2 stops21h 11mMultiple Airlines

Deal found 12/30

$686

Mon 1/121:55 pmHVN - SJU

Nonstop3h 58mMultiple Airlines

Fri 1/162:41 pmSJU - HVN

1 stop8h 38mMultiple Airlines

Deal found 12/29

$214

Mon 1/121:55 pmHVN - SJU

Nonstop3h 58mAvelo Airlines

Fri 1/167:54 pmSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/29

$227

Wed 1/146:30 amHVN - SJU

Nonstop3h 58mAvelo Airlines

Fri 1/307:54 pmSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/30

$215

Wed 1/146:30 amHVN - SJU

Nonstop3h 58mMultiple Airlines

Fri 1/306:00 amSJU - HVN

1 stop7h 56mMultiple Airlines

Deal found 12/30

$276

Thu 1/152:26 pmHVN - SJU

1 stop9h 45mMultiple Airlines

Sat 1/178:00 amSJU - HVN

2 stops34h 18mMultiple Airlines

Deal found 12/29

$267

Wed 1/216:30 amHVN - SJU

Nonstop3h 58mAvelo Airlines

Sat 1/2412:28 pmSJU - HVN

Nonstop4h 05mAvelo Airlines

Deal found 12/30

$178

Wed 1/216:30 amHVN - SJU

Nonstop3h 58mMultiple Airlines

Wed 1/286:00 amSJU - HVN

1 stop9h 23mMultiple Airlines

Deal found 12/31

$212

Wed 1/216:30 amHVN - SJU

Nonstop3h 58mMultiple Airlines

Sat 1/248:00 amSJU - HVN

1 stop7h 23mMultiple Airlines

Deal found 12/30

$270

Thu 1/225:58 pmHVN - SJU

2 stops29h 01mMultiple Airlines

Tue 1/276:00 amSJU - HVN

1 stop9h 01mMultiple Airlines

Deal found 12/30

$271

One-way flights from New Haven to Caribbean Islands
Search for one-way flight options from New Haven to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated December 31, 2025.

Sat 1/246:30 amHVN - SJU

Nonstop3h 58mAvelo Airlines

Deal found 12/29

$93

Sun 1/48:59 pmHVN - SJU

Nonstop3h 54mAvelo Airlines

Deal found 12/30

$113

Tue 1/68:30 amHVN - SJU

1 stop14h 14mMultiple Airlines

Deal found 12/29

$125

Sun 1/255:58 pmHVN - SJU

2 stops28h 38mMultiple Airlines

Deal found 12/31

$136

Mon 1/56:26 pmHVN - SJU

1 stop22h 27mMultiple Airlines

Deal found 12/29

$150

Thu 1/155:58 pmHVN - SJU

2 stops31h 32mMultiple Airlines

Deal found 12/30

$159

Sat 1/248:00 amHVN - SJU

1 stop14h 33mMultiple Airlines

Deal found 12/29

$164

Sat 1/37:45 amHVN - SJU

Nonstop3h 54mAvelo Airlines

Deal found 12/29

$181

Thu 2/268:59 pmHVN - PUJ

1 stop15h 24mMultiple Airlines

Deal found 12/30

$189

Find flight deals from New Haven to Caribbean Islands

Round-trip from	$178 (Super.com)
One-way from	$93 (eDestinos)
Popular in	December
Cheapest in	March
Average price	$365

From Tweed-New Haven to Caribbean Islands

Search Deals

One-way flight from Tweed-New Haven to Caribbean Islands

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($24 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

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Haven to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 3/22

8:59 pm-12:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 3/28

11:30 am-3:35 pm

Nonstop4h 05m

$201

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 1/21

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:00 am-2:23 pm

1 stop9h 23m

$212

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 1/12

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 1/16

2:41 pm-10:19 pm

1 stop8h 38m

$214

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 1/14

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 1/30

7:54 pm-10:59 pm

Nonstop4h 05m

$215

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 1/28

8:00 am-11:33 pm

1 stop14h 33m

San Juan Luis Munoz Marin Intl

Wed 2/4

6:00 am-2:23 pm

1 stop9h 23m

$257

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 1/21

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sat 1/24

8:00 am-2:23 pm

1 stop7h 23m

$270

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 4/5

8:59 pm-12:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 4/8

11:30 am-3:35 pm

Nonstop4h 05m

$274

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 1/15

2:26 pm-1:11 am

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Wed 1/21

7:00 pm-11:27 am

2 stops41h 27m

$279

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Tue 3/10

2:46 pm-8:54 am

1 stop18h 08m

San Juan Luis Munoz Marin Intl

Thu 3/19

12:04 pm-8:04 pm

1 stop8h 00m

$284

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Sat 2/14

2:45 pm-2:00 pm

3 stops22h 15m

Punta Cana

Sat 2/21

5:47 am-2:34 pm

1 stop9h 47m

$467

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 24 results

Best time to book a flight from New Haven to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, February is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $59). Flying from New Haven to Caribbean Islands 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 EPX?

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 Islands as you normally would.

Reviews of airlines servicing Caribbean Islands

Read through reviews of airlines operating flights from New Haven to Caribbean Islands, such as JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

JetBlue

7.2

Good

2,901 reviews

Reviews

1 / 20

4.0

Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.

JetBlue

7.2

Good

2,901 reviews

JetBlue

7.2

Good

2,901 reviews

Reviews

1 / 20

4.0

Okay

Jeff,Dec 2025

LAX - BOS

We boarded an hour and a half late and the crew was very salty when asked why. Still got no reason other than someone took the intended plane? Won't fly with them again.

Related info for your journey

What airport do you fly from for flights from New Haven to Caribbean Islands?
Most people fly from Tweed-New Haven (HVN) if they book a flight from New Haven to Caribbean Islands. Tweed-New Haven is conveniently located just 3.6 mi from New Haven’s city center.
How long is the flight from New Haven to Caribbean Islands?
There are many flights that can get you from New Haven to Caribbean Islands in 3h 58m. Fly via Avelo Airlines to get the fastest option. Airlines will cover a distance of 1628 mi. All flights are typically nonstop.
What are the most popular routes from New Haven to Caribbean Islands?
Most travelers choose Tweed-New Haven - San Juan Luis Munoz Marin Intl, Tweed-New Haven - Punta Cana or Tweed-New Haven - Castries Hewanorra when deciding on the best route from New Haven to Caribbean Islands.
What are the cheapest flights from New Haven to Caribbean Islands?
Looking for the cheapest flight from New Haven to Caribbean Islands? While on average our users pay $285, our data indicates the cheapest price to be $211. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $214.
Can I find deals for flights from New Haven to Caribbean Islands that include hotel bookings?
Yes. In addition to deals on New Haven to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from New Haven to Caribbean Islands?
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 Islands.
Can I find deals for business class flights from New Haven to Caribbean Islands?
Yes. Cheapflights offers flight deals from New Haven to Caribbean Islands 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 Islands?
Currently, February is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $59). Flying from New Haven to Caribbean Islands 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

Top 3 airlines flying from New Haven to Caribbean Islands

Airline	Cheapest	Average	Flexibility	On-time
Frontier	Cheapest$98	Average$221	FlexibilityNo cancel fee	On-time62%
Avelo Airlines	Cheapest$197	Average$295	FlexibilityNo cancel fee	On-timeN/A
JetBlue	Cheapest$205	Average$464	FlexibilityNo cancel fee	On-time62%

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.

$93+ Cheap flights from New Haven (HVN) to Caribbean Islands

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 1/24. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from New Haven to Caribbean Islands with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from New Haven to Caribbean Islands

Cheapest flights from New Haven to Caribbean IslandsExplore the most affordable flight options available from New Haven to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.

Explore the most affordable flight options available from New Haven to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.

Find flight deals from New Haven to Caribbean Islands

Keep the following information in mind while searching for New Haven to Caribbean Islands flight deals. Data was last updated December 31, 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Cheapflights Fare Finder

Use the filters below to find and compare flights from New Haven to Caribbean Islands that are best for you.

Best time to book a flight from New Haven to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from New Haven with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from New Haven to Caribbean Islands

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

What is the cheapest time of day to fly from HVN to EPX?

Find hourly flight availability from New Haven to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 31, 2025.

Reviews of airlines servicing Caribbean Islands

Read through reviews of airlines operating flights from New Haven to Caribbean Islands, such as JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Related info for your journey

Find useful and relevant information for your journey from New Haven to Caribbean Islands. 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 Islands?

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

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

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

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

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

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

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

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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 3 airlines flying from New Haven to Caribbean Islands

100% Free

Book with Flexibility

Travel Smart

Cheapest flights from New Haven to Caribbean Islands
Explore the most affordable flight options available from New Haven to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 31, 2025.