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$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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
HVN — SJU
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
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 February 20, 2025.

Round-trip from

$198
(Mytrip)

One-way from

$100
(CheapOair)

Popular in

December

Cheapest in

September

Average price

$309

Good round-trip deal

$226 or less

Good one-way deal

$100 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. 10% potential increase in price ($34 potential increase over avg. RT price).
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Cheapest flight prices on average. 8% potential price decrease ($23 potential savings vs. average RT price).
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Average for round-trip flights in February 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 February 20, 2025.

This eDestinos deal was found by Cheapflights users on 2/19. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/218:50 amHVN - SJU
Nonstop4h 03mAvelo Airlines
Fri 3/281:55 pmSJU - HVN
Nonstop4h 05mAvelo Airlines
Deal found 2/19$181
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Mon 3/105:20 pmHVN - SJU
1 stop9h 03mMultiple Airlines
Fri 3/146:18 amSJU - HVN
1 stop10h 12mMultiple Airlines
Deal found 2/19$194
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Fri 3/75:20 pmHVN - STT
1 stop15h 11mMultiple Airlines
Tue 3/111:40 pmSTT - HVN
1 stop9h 05mMultiple Airlines
Deal found 2/20$269
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 4/265:35 pmHVN - PUJ
1 stop18h 09mMultiple Airlines
Sat 5/33:48 pmPUJ - HVN
2 stops22h 39mMultiple Airlines
Deal found 2/19$388
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Sun 3/236:15 pmHVN - MBJ
2 stops17h 47mMultiple Airlines
Sat 3/2911:30 amMBJ - HVN
2 stops28h 55mMultiple Airlines
Deal found 2/20$400
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Wed 3/193:15 pmHVN - KIN
2 stops22h 13mMultiple Airlines
Sun 3/231:36 pmKIN - HVN
2 stops23h 24mMultiple Airlines
Deal found 2/20$412
This Mytrip deal was found by Cheapflights users on 2/20. 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.
Thu 3/1310:30 amHVN - NAS
2 stops28h 15mMultiple Airlines
Mon 3/174:00 pmNAS - HVN
2 stops30h 45mMultiple Airlines
Deal found 2/20$475
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Sat 4/128:00 amHVN - AUA
2 stops30h 40mMultiple Airlines
Sat 4/193:50 pmAUA - HVN
2 stops23h 00mMultiple Airlines
Deal found 2/19$845
This Mytrip deal was found by Cheapflights users on 2/19. 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.
Tue 2/251:53 pmHVN - POP
2 stops24h 48mMultiple Airlines
Mon 3/31:50 pmPOP - HVN
2 stops33h 55mMultiple Airlines
Deal found 2/19$1,545

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 February 20, 2025.

Fly from

New Haven

Fly to

Caribbean

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 3/21

8:50 am-12:53 pm

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Fri 3/28

1:55 pm-6:00 pm

Nonstop4h 05m

$181

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 3/10

5:20 pm-2:23 am

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Fri 3/14

6:18 am-4:30 pm

1 stop10h 12m

$194

New HavenSaint Thomas Island

HVN - STT

HVNSTT

Tweed-New Haven

Fri 3/7

5:20 pm-9:31 am

1 stop15h 11m

Saint Thomas Island Cyril E King

Tue 3/11

1:40 pm-10:45 pm

1 stop9h 05m

$269

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Sat 4/26

5:35 pm-11:44 am

1 stop18h 09m

Punta Cana

Sat 5/3

3:48 pm-2:27 pm

2 stops22h 39m

$388

New HavenMontego Bay

HVN - MBJ

HVNMBJ

Tweed-New Haven

Sun 3/23

6:15 pm-11:02 am

2 stops17h 47m

Montego Bay Sangster Intl

Sat 3/29

11:30 am-5:25 pm

2 stops28h 55m

$400

New HavenKingston

HVN - KIN

HVNKIN

Tweed-New Haven

Wed 3/19

3:15 pm-12:28 pm

2 stops22h 13m

Kingston Norman Manley

Sun 3/23

1:36 pm-2:00 pm

2 stops23h 24m

$412

New HavenNassau

HVN - NAS

HVNNAS

Tweed-New Haven

Thu 3/13

10:30 am-2:45 pm

2 stops28h 15m

Nassau Intl

Mon 3/17

4:00 pm-10:45 pm

2 stops30h 45m

$475

New HavenOranjestad

HVN - AUA

HVNAUA

Tweed-New Haven

Sat 4/12

8:00 am-2:40 pm

2 stops30h 40m

Oranjestad Reina Beatrix

Sat 4/19

3:50 pm-2:50 pm

2 stops23h 00m

$845

New HavenPuerto Plata

HVN - POP

HVNPOP

Tweed-New Haven

Tue 2/25

1:53 pm-3:41 pm

2 stops24h 48m

Puerto Plata La Union

Mon 3/3

1:50 pm-10:45 pm

2 stops33h 55m

$1,545

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 3/3

2:20 pm-7:13 pm

Nonstop3h 53m

$100

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 12 results
1
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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 $363). 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 February 20, 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 February 20, 2025.
Avelo Airlines
7.5
Good

Comfort

7.1

Overall

7.5

Crew

8.4

Food

5.2

Boarding

7.8

Entertainment

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
7.5
Good
Avelo Airlines
7.5
Good

Comfort

7.1

Overall

7.5

Crew

8.4

Food

5.2

Boarding

7.8

Entertainment

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 - Punta Cana or Tweed-New Haven - Saint Thomas Island Cyril E King 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 $96. On average you can expect to pay $249. 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 $363). 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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Alternative routes for New Haven to Caribbean

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 February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$205FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$196Average$298FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$208Average$344FlexibilityNo cancel feeOn-time62%
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