HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean Islands

$120+ 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 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

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

Round-trip from

$245
(FlightHub)

One-way from

$120
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$217
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. 7% potential increase in price ($21 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 2025
Search Deals

Find 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 March 31, 2025.

This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/287:30 amHVN - SJU
Nonstop3h 45mAvelo Airlines
Wed 5/711:15 amSJU - HVN
Nonstop4h 05mAvelo Airlines
Deal found 3/30$200
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/286:30 amHVN - SJU
3 stops37h 10mMultiple Airlines
Wed 5/711:15 amSJU - HVN
Nonstop4h 05mMultiple Airlines
Deal found 3/30$225
This Kiwi.com deal was found by Cheapflights users on 3/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/156:10 pmHVN - PUJ
2 stops20h 07mMultiple Airlines
Thu 5/229:52 amPUJ - HVN
1 stop22h 55mMultiple Airlines
Deal found 3/30$394
This Kiwi.com deal was found by Cheapflights users on 3/31. 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 5/26:30 pmHVN - NAS
1 stop21h 55mMultiple Airlines
Fri 5/912:00 pmNAS - HVN
1 stop23h 30mMultiple Airlines
Deal found 3/31$469
This Mytrip deal was found by Cheapflights users on 3/31. 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 5/217:00 amHVN - MBJ
1 stop6h 45mMultiple Airlines
Sun 5/2512:07 pmMBJ - HVN
2 stops28h 46mMultiple Airlines
Deal found 3/31$636
This Mytrip deal was found by Cheapflights users on 3/31. 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 5/156:30 amHVN - CUR
2 stops34h 00mMultiple Airlines
Thu 5/2210:05 amCUR - HVN
3 stops31h 48mMultiple Airlines
Deal found 3/31$847

Cheapflights Fare Finder

Customize your flight search to find flights from New Haven to Caribbean Islands 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 March 31, 2025.
Use the filters below to find and compare flights from New Haven to Caribbean Islands that are best for you.

Fly from

New Haven

Fly to

Caribbean Islands

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 5/28

6:30 am-10:15 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Wed 6/4

11:15 am-3:20 pm

Nonstop4h 05m

$245

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 4/25

7:30 am-11:15 am

Nonstop3h 45m

San Juan Luis Munoz Marin Intl

Tue 4/29

12:54 am-10:59 pm

3 stops46h 05m

$270

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Thu 5/15

6:10 pm-2:17 pm

2 stops20h 07m

Punta Cana

Thu 5/22

9:52 am-8:47 am

1 stop22h 55m

$394

New HavenNassau

HVN - NAS

HVNNAS

Tweed-New Haven

Fri 5/2

6:30 pm-4:25 pm

1 stop21h 55m

Nassau Intl

Fri 5/9

12:00 pm-11:30 am

1 stop23h 30m

$469

New HavenMontego Bay

HVN - MBJ

HVNMBJ

Tweed-New Haven

Wed 5/21

7:00 am-12:45 pm

1 stop6h 45m

Montego Bay Sangster Intl

Sun 5/25

12:07 pm-5:53 pm

2 stops28h 46m

$636

New HavenWillemstad

HVN - CUR

HVNCUR

Tweed-New Haven

Thu 5/15

6:30 am-4:30 pm

2 stops34h 00m

Willemstad Hato Int.

Thu 5/22

10:05 am-5:53 pm

3 stops31h 48m

$847

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/31

6:30 am-10:15 am

Nonstop3h 45m

$120

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 5/2

4:20 pm-11:39 pm

2 stops31h 19m

$133

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/31

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, September is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $254). Flying from New Haven to Caribbean Islands in December is currently the most expensive (average of $336). 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?

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 March 31, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

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.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

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).

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated March 31, 2025.
Avelo Airlines
7.5
Good

Boarding

7.8

Overall

7.5

Entertainment

5.1

Crew

8.4

Food

5.2

Comfort

7.1

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
7.5
Good
Avelo Airlines
7.5
Good

Boarding

7.8

Overall

7.5

Entertainment

5.1

Crew

8.4

Food

5.2

Comfort

7.1

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 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?

    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.

  • 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 - Montego Bay Sangster Intl or Tweed-New Haven - Kingston Norman Manley 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 $221, our data indicates the cheapest price to be $100. The most popular route (Tweed-New Haven - San Juan Luis Munoz Marin Intl), is priced around $200.

  • 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, September is the cheapest month in which you can book a flight from New Haven to Caribbean Islands (average of $254). Flying from New Haven to Caribbean Islands in December is currently the most expensive (average of $336). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.
LaGuardia to Miami flights
Newark to Fort Lauderdale flights
Newark to Cancún flights
John F Kennedy Intl 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 Miami flights
Newark to Orlando flights
Newark to Las Vegas flights
LaGuardia to Orlando flights
LaGuardia to Dallas/Fort Worth flights
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Mexico City flights
Newark to Los Angeles flights
Newark to Seattle flights
Newark to Dallas/Fort Worth flights
LaGuardia to Atlanta flights
Newark to Tampa flights
John F Kennedy Intl to Seattle flights
John F Kennedy Intl to San Francisco flights
LaGuardia to Cancún flights
LaGuardia to O'Hare Intl flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Sky Harbor Intl flights
Newark to New Orleans flights
LaGuardia to Las Vegas flights
John F Kennedy Intl to O'Hare Intl flights
LaGuardia to Los Angeles flights
John F Kennedy Intl to Denver flights
John F Kennedy Intl to Dallas/Fort Worth flights
Newark to Denver flights
Newark to Mexico City flights
Newark to O'Hare Intl flights
John F Kennedy Intl to Tampa flights
LaGuardia to New Orleans flights
Newark to Sky Harbor Intl flights
John F Kennedy Intl to Atlanta flights
LaGuardia to Tampa flights
John F Kennedy Intl to Hobby flights
Newark to San Francisco flights
Newark to Austin flights
John F Kennedy Intl to Honolulu flights
John F Kennedy Intl to Austin flights
Newark to Atlanta flights
John F Kennedy Intl to San Diego flights
John F Kennedy Intl to New Orleans flights
John F Kennedy Intl to Nashville flights

Top 3 airlines flying from New Haven to Caribbean Islands

Discover the top 3 airlines that operate flights from New Haven to Caribbean Islands. 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 March 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$188FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$355FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$286FlexibilityNo 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.