$74 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 3/2. 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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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 Cana1 stop$466
Montego Bay
Montego Bay3 stops$430
Oranjestad
Oranjestad2 stops$787
Nassau
Nassau2 stops$449
Saint Thomas Island
Saint Thomas Island2 stops$282
Simpson Bay
Simpson Bay2 stops$422
Punta Cana
Punta Cana1 stop$466
Montego Bay
Montego Bay3 stops$430
Oranjestad
Oranjestad2 stops$787
Nassau
Nassau2 stops$449
Saint Thomas Island
Saint Thomas Island2 stops$282
Simpson Bay
Simpson Bay2 stops$422

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

Sat, Apr 25 - Wed, Apr 29
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$144Avelo Airlines
Wed, Apr 22 - Wed, Apr 29
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$157Avelo Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
7:00 pm - 10:47 am
HVN
-
SJU
14h 47m
1 stop
Multiple Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$192Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
7:00 pm - 3:31 pm
HVN
-
SJU
19h 31m
2 stops
Multiple Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$194Multiple Airlines
Sat, Apr 25 - Mon, Apr 27
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$200Avelo Airlines
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
12:07 pm - 3:06 pm
HVN
-
SJU
25h 59m
2 stops
Multiple Airlines Logo
4:22 pm - 11:27 am
SJU
-
HVN
20h 05m
1 stop
$219Multiple Airlines
Wed, Apr 22 - Wed, Apr 29
Multiple Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Multiple Airlines Logo
7:00 am - 2:32 pm
SJU
-
HVN
7h 32m
1 stop
$237Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
11:21 am - 11:09 pm
HVN
-
SJU
34h 48m
3 stops
Multiple Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$238Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Avelo Airlines Logo
8:30 am - 1:20 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$239Avelo Airlines
Mon, Feb 23 - Fri, Feb 27
Avelo Airlines Logo
8:30 am - 1:20 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$245Avelo 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 $134 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 $134.

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 $162, 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 $607 and $323 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 Saturday, 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$74
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly and prices are also 23% 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 afternoon, when round-trip flights cost $232 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 $284.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from New Haven to the following destinations at these prices or less: San Juan $167 one-way - $193 round-trip

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 2892 reviews
7.4Boarding
7.5Comfort
7.2Entertainment
6.6Food
8.0Crew
Airline reviews

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

2.0 MediocreAnonymous, Feb 2026
BOS - LAS
Read more JetBlue reviews

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

Friendly crew, efficient boarding and flight arrived early. Couldn’t ask for a better experience

Terrible. They canceled our early morning flight after midnight on the day of and had no available flights to rebook my family on for the next 72 hours. Yet they still had other flights that were not cancelled from JFK so it couldn’t be based on the weather. It felt like they canceled the flight based on it not being profitable enough for them. I am not interested in traveling with the again. The absolute worse customer service and lack of accountability.

Horribly rude check in at airport, worst in 25 years of flying. All over a simple issue they could have googled to resolve.

First time flying with JetBlue and never again. I went to the counter to request meet and assist because I'm 74 and my wife is 79. I walk with a cane and my wife is handicapped and has her own wheel chair. I told the agent that my wife and luggage was at the entrance door. The ticketing agent said to me that they don't offer meet and assist. I need to bring them our luggage and then go back and get my wife in order to get my boarding pass. As I went back to get my luggage a Southwest agent along with a TSA agent recognized the situation and came over and took my wife and luggage to the JetBlue ticketing counter alongside the line and told the JetBlue agent to issue to take our luggage as soon as they could.

Flight was fine, price was good but food onboard was abysmal. I was on there for breakfast and lunch and dinner 845am EST to 845pm GMT and all I got was a yoghurt parfait, fruit and a piece of cake. Later snacks included an ice-cream brownie and a pizza twist. I was hungry by the time I landed and the airport amenities were closed. Not happy.

1) No pilot available for 1 hour 2) no room for most passengers careyon in overhead—-> stowed below 3) when we landed we had to wait 45 min. Before docking at gate as gate was not ready

Good. No issues except a slight delay. Crew came in late.

Not a pleasant experience, service was poor. Didn't like it

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

New Haven (HVN)