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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
січ. 26 — лют. 21
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Cheap flight deals from New Haven to Caribbean

Discover tips and strategies to find the most affordable flight options for your journey from New Haven (HVN) to Caribbean (0CB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated січень 21, 2025.

Round-trip from

$200
(Gotogate)

One-way from

$100
(CheapOair)

Good round-trip deal

$266 or less

Good one-way deal

$119 or less
From Tweed-New Haven to Caribbean
One-way flight from Tweed-New Haven to Caribbean
Price to beat on a round-trip flight from Tweed-New Haven to Caribbean.
Price to beat on a one-way flight from Tweed-New Haven to Caribbean.

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 січень 21, 2025.

This CheapOair deal was found by Cheapflights users on 1/20. 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.
сб 3/112:45 pmHVN - SJU
Nonstop3h 53mAvelo Airlines
сб 3/88:10 pmSJU - HVN
Nonstop4h 05mAvelo Airlines
Deal found 1/20$200
This Mytrip deal was found by Cheapflights users on 1/20. 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.
пн 2/37:15 amHVN - SJU
2 stops25h 06mMultiple Airlines
чт 2/610:09 pmSJU - HVN
2 stops22h 52mMultiple Airlines
Deal found 1/20$215
This Mytrip deal was found by Cheapflights users on 1/20. 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.
пн 2/246:20 pmHVN - PUJ
2 stops20h 23mMultiple Airlines
пн 3/34:48 pmPUJ - HVN
2 stops21h 12mMultiple Airlines
Deal found 1/20$354
This Mytrip deal was found by Cheapflights users on 1/20. 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.
ср 3/56:20 pmHVN - MBJ
2 stops17h 42mMultiple Airlines
ср 3/1212:07 pmMBJ - HVN
2 stops21h 08mMultiple Airlines
Deal found 1/20$419
This Mytrip deal was found by Cheapflights users on 1/19. 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.
чт 2/208:31 pmHVN - KIN
2 stops15h 50mMultiple Airlines
пн 2/243:30 pmKIN - HVN
2 stops30h 04mMultiple Airlines
Deal found 1/19$445
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
чт 3/66:10 pmHVN - NAS
1 stop22h 15mMultiple Airlines
чт 3/1312:00 pmNAS - HVN
1 stop21h 45mMultiple Airlines
Deal found 1/21$475
This Mytrip deal was found by Cheapflights users on 1/19. 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.
чт 2/208:31 pmHVN - SXM
2 stops16h 59mMultiple Airlines
пн 2/243:25 pmSXM - HVN
3 stops31h 09mMultiple Airlines
Deal found 1/19$484
This Mytrip deal was found by Cheapflights users on 1/20. 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.
пн 3/1010:30 amHVN - UVF
2 stops28h 15mMultiple Airlines
пн 3/173:45 pmUVF - HVN
2 stops29h 49mMultiple Airlines
Deal found 1/20$1,129
This Mytrip deal was found by Cheapflights users on 1/20. 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.
нд 3/98:15 amHVN - ANU
3 stops27h 25mMultiple Airlines
пн 3/102:45 pmANU - HVN
3 stops22h 15mMultiple Airlines
Deal found 1/20$1,507

Find flights from New Haven to Caribbean within your budget

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 січень 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

сб 3/1

12:45 pm-5:38 pm

Nonstop3h 53m

San Juan Luis Munoz Marin Intl

ср 3/5

1:20 pm-4:25 pm

Nonstop4h 05m

$200

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

пн 2/3

7:15 am-9:21 am

2 stops25h 06m

San Juan Luis Munoz Marin Intl

чт 2/6

10:09 pm-8:01 pm

2 stops22h 52m

$215

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

чт 2/20

6:10 pm-12:42 pm

1 stop17h 32m

Punta Cana

чт 2/27

4:48 pm-9:45 am

2 stops41h 57m

$388

New HavenMontego Bay

HVN - MBJ

HVNMBJ

Tweed-New Haven

ср 3/5

6:20 pm-12:02 pm

2 stops17h 42m

Montego Bay Sangster Intl

ср 3/12

12:07 pm-10:15 am

2 stops21h 08m

$419

New HavenKingston

HVN - KIN

HVNKIN

Tweed-New Haven

чт 2/20

8:31 pm-12:21 pm

2 stops15h 50m

Kingston Norman Manley

пн 2/24

3:30 pm-9:34 pm

2 stops30h 04m

$445

New HavenNassau

HVN - NAS

HVNNAS

Tweed-New Haven

чт 3/6

6:10 pm-4:25 pm

1 stop22h 15m

Nassau Intl

чт 3/13

12:00 pm-9:45 am

1 stop21h 45m

$475

New HavenSimpson Bay

HVN - SXM

HVNSXM

Tweed-New Haven

чт 2/20

8:31 pm-2:30 pm

2 stops16h 59m

Simpson Bay Princess Juliana

пн 2/24

3:25 pm-9:34 pm

3 stops31h 09m

$484

New HavenCastries

HVN - UVF

HVNUVF

Tweed-New Haven

пн 3/10

10:30 am-2:45 pm

2 stops28h 15m

Castries Hewanorra

пн 3/17

3:45 pm-9:34 pm

2 stops29h 49m

$1,129

New HavenSt. John's

HVN - ANU

HVNANU

Tweed-New Haven

нд 3/9

8:15 am-11:40 am

3 stops27h 25m

St. John's V.C. Bird Intl

пн 3/10

2:45 pm-1:00 pm

3 stops22h 15m

$1,507

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

пн 2/24

2:20 pm-7:13 pm

Nonstop3h 53m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/21

Showing 1-10 of 13 results
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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.

Travel insights for flights from New Haven to Caribbean

Get recent, data-driven insights about flights from New Haven to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $378). 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 січень 21, 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.

Rainfall in Caribbean by month

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

In terms of precipitation, rainfall in Caribbean 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 when rainfall is around 2.2 in.

Temperature in Caribbean by month

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

If weather is an important factor for your trip to Caribbean, 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

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 січень 21, 2025.
Avelo Airlines
7.5
Good
74 reviews

Boarding

7.8

Entertainment

5.1

Comfort

7.1

Crew

8.4

Overall

7.5

Food

5.2

Reviews

1 / 6

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
74 reviews
Avelo Airlines
7.5
Good
74 reviews

Boarding

7.8

Entertainment

5.1

Comfort

7.1

Crew

8.4

Overall

7.5

Food

5.2

Reviews

1 / 6

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?

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

    The cheapest flight price from New Haven to Caribbean is $97. On average you can expect to pay $253. The most popular route, (Tweed-New Haven - San Juan Luis Munoz Marin Intl), can usually be booked for $200.

  • 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 March is currently the most expensive (average of $378). 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

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Alternative routes for New Haven to Caribbean

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

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 січень 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$188FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$126Average$320FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$193Average$315FlexibilityNo cancel feeOn-timeN/A
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