$111 Find Cheap Flights from New Haven to Caribbean Islands - Compare and Save

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 9/21. 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 Cana2 stops$769
Montego Bay
Montego Bay2 stops$878
Oranjestad
Oranjestad2 stops$1,112
Nassau
Nassau2 stops$596
Saint Thomas Island
Saint Thomas Island1 stop$1,271
Kingston
Kingston2 stops$1,100
St. John's
St. John's3 stops$1,242
Punta Cana
Punta Cana2 stops$769
Montego Bay
Montego Bay2 stops$878
Oranjestad
Oranjestad2 stops$1,112
Nassau
Nassau2 stops$596
Saint Thomas Island
Saint Thomas Island1 stop$1,271
Kingston
Kingston2 stops$1,100
St. John's
St. John's3 stops$1,242

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

Thu, Aug 27 - Tue, Sep 1
Multiple Airlines Logo
5:27 pm - 12:56 am
HVN
-
SJU
31h 29m
2 stops
Multiple Airlines Logo
8:57 pm - 2:57 pm
SJU
-
HVN
18h 00m
1 stop
$282Multiple Airlines
Mon, Sep 28 - Mon, Oct 5
Avelo Airlines Logo
7:00 am - 10:57 am
HVN
-
SJU
3h 57mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$299Avelo Airlines
Fri, Sep 11 - Fri, Sep 18
Avelo Airlines Logo
7:00 am - 10:57 am
HVN
-
SJU
3h 57mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$315Avelo Airlines
Fri, Sep 11 - Fri, Sep 18
Avelo Airlines Logo
7:00 am - 10:57 am
HVN
-
SJU
3h 57mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$326Avelo Airlines
Fri, Sep 11 - Fri, Sep 18
Avelo Airlines Logo
7:00 am - 10:57 am
HVN
-
SJU
3h 57mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$330Avelo Airlines
Fri, Aug 28 - Mon, Aug 31
Avelo Airlines Logo
6:30 am - 10:20 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
11:30 am - 3:27 pm
SJU
-
HVN
3h 57mnonstop
$334Avelo Airlines
Sun, Jul 26 - Thu, Aug 20
Multiple Airlines Logo
6:31 pm - 2:00 pm
HVN
-
SJU
19h 29m
1 stop
Multiple Airlines Logo
7:00 am - 5:46 pm
SJU
-
HVN
10h 46m
1 stop
$350Multiple Airlines
Sat, Aug 29 - Tue, Sep 1
Multiple Airlines Logo
3:42 pm - 8:11 am
HVN
-
SJU
16h 29m
1 stop
Multiple Airlines Logo
6:09 pm - 2:57 pm
SJU
-
HVN
20h 48m
1 stop
$352Multiple Airlines
Sat, Aug 29 - Mon, Aug 31
Multiple Airlines Logo
3:42 pm - 8:11 am
HVN
-
SJU
16h 29m
1 stop
Multiple Airlines Logo
5:37 pm - 12:26 pm
SJU
-
HVN
18h 49m
2 stops
$354Multiple Airlines
Fri, Aug 28 - Mon, Aug 31
Avelo Airlines Logo
6:30 am - 10:20 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
11:30 am - 3:27 pm
SJU
-
HVN
3h 57mnonstop
$355Avelo 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 5 days was to San Juan, at $149 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 5 days was $149.

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

The average price for all round-trip flights from New Haven to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $208 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 $322.

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 $225, prices are generally cheapest when you fly direct.

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 Mondays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Caribbean Islands, Monday is the cheapest day to fly and Saturday 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 23 weeks before departure.

Find deals

Good to know

Low seasonSeptember
Cheapest flight$111
Best time to beat the crowds with an average 19% drop in price.
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.

  • How many flights are there between New Haven and Caribbean Islands per day?

    There is a maximum of 1 nonstop flight a day that takes off from New Haven and lands in Caribbean Islands, with an average flight time of 3h 50m. The most common departure time is 7:00 am and most flights take off in the morning. Each week, there are 4 flights.

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 $187 one-way - $323 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.
7.1
JetBlueOverall score based on 3001 reviews
7.9Crew
7.3Boarding
7.2Entertainment
7.5Comfort
6.6Food
Airline reviews

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

2.0 MediocrePaula, Jun 2026
DCA - BOS
Read more JetBlue reviews

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

Seamless flight, didn’t feel like five hours at all very smooth ride. Watched two good movies didn’t even realize I was on a plane. The staff were extremely nice and helpful.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

New Haven (HVN)