$100 Find Cheap Flights from New Haven to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from New Haven to Caribbean Islands departing on 2/19. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from New Haven to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana3 stops$442
Montego Bay
Montego Bay3 stops$490
Saint Thomas Island
Saint Thomas Island1 stop$385
Simpson Bay
Simpson Bay3 stops$436
Providenciales
Providenciales3 stops$695
Punta Cana
Punta Cana3 stops$442
Montego Bay
Montego Bay3 stops$490
Saint Thomas Island
Saint Thomas Island1 stop$385
Simpson Bay
Simpson Bay3 stops$436
Providenciales
Providenciales3 stops$695

Book Cheap New Haven to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from New Haven to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from New Haven to Caribbean Islands

Mon, Feb 2 - Fri, Feb 6
Avelo Airlines Logo
1:55 pm - 6:53 pm
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$239Avelo Airlines
Mon, Jan 26 - Fri, Feb 6
Avelo Airlines Logo
1:55 pm - 6:53 pm
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$241Avelo Airlines
Sat, Jan 17 - Mon, Feb 9
Avelo Airlines Logo
6:30 am - 11:28 am
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$263Avelo Airlines
Sun, Mar 8 - Thu, Mar 12
Avelo Airlines Logo
8:59 pm - 12:49 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
2:40 am - 6:45 am
SJU
-
HVN
4h 05mnonstop
$265Avelo Airlines
Mon, Jan 5 - Sat, Jan 10
Multiple Airlines Logo
6:26 pm - 5:53 pm
HVN
-
SJU
22h 27m1 stop
Multiple Airlines Logo
4:12 pm - 1:41 pm
SJU
-
HVN
22h 29m1 stop
$266Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
Multiple Airlines Logo
5:58 pm - 2:32 pm
HVN
-
SJU
43h 34m2 stops
Multiple Airlines Logo
8:00 am - 7:04 pm
SJU
-
HVN
12h 04m1 stop
$267Multiple Airlines
Thu, Feb 19 - Sat, Mar 7
Avelo Airlines Logo
8:59 pm - 1:49 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:30 pm - 3:35 pm
SJU
-
HVN
4h 05mnonstop
$269Avelo Airlines
Sat, Jan 10 - Thu, Jan 15
Multiple Airlines Logo
6:30 am - 11:28 am
HVN
-
SJU
3h 58mnonstop
Multiple Airlines Logo
6:00 am - 1:27 pm
SJU
-
HVN
8h 27m1 stop
$273Multiple Airlines
Mon, Mar 23 - Thu, Mar 26
Multiple Airlines Logo
7:30 am - 9:57 am
HVN
-
SJU
26h 27m1 stop
Multiple Airlines Logo
2:40 am - 6:45 am
SJU
-
HVN
4h 05mnonstop
$288Multiple Airlines
Fri, Jan 9 - Mon, Jan 12
Multiple Airlines Logo
12:07 pm - 11:44 pm
HVN
-
SJU
10h 37m2 stops
Multiple Airlines Logo
9:23 pm - 2:01 pm
SJU
-
HVN
17h 38m1 stop
$290Multiple Airlines
Booking Insights

KAYAK's insights & trends for New Haven to Caribbean Islands flights

Get data-powered insights and trends into flights from New Haven to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New Haven to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from New Haven found in the last 72 hours was to San Juan, at $181 round-trip. The most popular route is from New Haven (HVN) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $181.

Can I save money by flying with a layover from New Haven to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $185, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from New Haven to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from New Haven to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from New Haven to Caribbean Islands is October, when tickets cost $228 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $669 and $412 respectively.

What’s the cheapest day of the week to fly from New Haven to Caribbean Islands?

The average price of all round-trip flights from New Haven to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from New Haven to Caribbean Islands, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday is the cheapest day to fly and Wednesday is the most expensive.

How far in advance should I book a flight from New Haven to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from New Haven to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from New Haven to Caribbean Islands, you should book around 4 weeks before departure, which saves you about 3% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$101
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from New Haven to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from New Haven to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from New Haven to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New Haven to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New Haven to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from New Haven to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from New Haven to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from New Haven to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from New Haven to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $170 on average. Morning departures are around 69% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $287.

Reviews of the top airline flying from New Haven to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from New Haven to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from New Haven to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.2
JetBlueOverall score based on 2897 reviews
7.4Boarding
6.7Food
8.0Crew
7.2Entertainment
7.6Comfort
Airline reviews

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

10.0 ExcellentJeff, Nov 2025
BOS - JFK
Read more JetBlue reviews

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

New Haven (HVN)