$93 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 4/27. 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 Cana1 stop$503
Montego Bay
Montego Bay3 stops$1,801
Oranjestad
Oranjestad1 stop$717
Nassau
Nassau1 stop$553
Kingston
Kingston3 stops$1,567
Simpson Bay
Simpson Bay2 stops$559
Punta Cana
Punta Cana1 stop$503
Montego Bay
Montego Bay3 stops$1,801
Oranjestad
Oranjestad1 stop$717
Nassau
Nassau1 stop$553
Kingston
Kingston3 stops$1,567
Simpson Bay
Simpson Bay2 stops$559

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

lun., jun. 8 - vie., jun. 12
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$205Avelo Airlines
lun., jun. 8 - vie., jun. 12
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$212Avelo Airlines
lun., jun. 8 - vie., jun. 12
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$215Avelo Airlines
lun., may. 18 - vie., may. 22
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$222Avelo Airlines
lun., may. 25 - vie., jun. 5
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$224Avelo Airlines
lun., ago. 31 - vie., sep. 11
Avelo Airlines Logo
6:30 am - 10:20 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
11:38 am - 3:45 pm
SJU
-
HVN
4h 07mnonstop
$225Avelo Airlines
sáb., may. 9 - vie., may. 15
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
$244Avelo Airlines
vie., may. 8 - vie., may. 22
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$245Avelo Airlines
lun., may. 25 - jue., may. 28
Multiple Airlines Logo
8:00 am - 8:19 pm
HVN
-
PUJ
12h 19m
1 stop
Multiple Airlines Logo
9:29 pm - 4:50 pm
PUJ
-
HVN
19h 21m
1 stop
$503Multiple Airlines
dom., abr. 26 - sáb., may. 2
Multiple Airlines Logo
8:30 am - 4:25 pm
HVN
-
NAS
7h 55m
1 stop
Multiple Airlines Logo
12:00 pm - 9:17 pm
NAS
-
HVN
9h 17m
1 stop
$553Multiple 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 $179 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 $179.

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 $198 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 $313.

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 $207, 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 $196 (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 $352 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 Friday, as it's usually the priciest day. When flying back from Caribbean Islands, Friday 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 16 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$93
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 2% increase 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.

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 $220 one-way - $278 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 2905 reviews
7.2Entertainment
7.5Comfort
8.0Crew
6.6Food
7.4Boarding
Airline reviews

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

6.0 GoodFrank, Mar 2026
FLL - LAS
Read more JetBlue reviews

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

Flight cancelled 2 hours prior to boarding. No explanation. No refunds.

Delayed by 1.5 hours. Terrible apologies, half hearted at best. It will be a LONG time until i book w Jet Blue again. Very disappointed.

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

They made me check my bag and I didn't need to as there was overhead space available. I paid for a seat towards the front of the plane and it didn't recline. I requested a refund and they declined to give me one.

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports