$80 Find Cheap Flights from New Haven to Caribbean

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 departing on 5/11. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from New Haven to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$456
Montego Bay
Montego Bay2 stops$848
Oranjestad
Oranjestad3 stops$877
Nassau
Nassau1 stop$546
Punta Cana
Punta Cana1 stop$456
Montego Bay
Montego Bay2 stops$848
Oranjestad
Oranjestad3 stops$877
Nassau
Nassau1 stop$546

Book Cheap New Haven to Caribbean 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 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

Sat, Jun 6 - Wed, Jun 10
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
$168Avelo Airlines
Fri, Jun 5 - Fri, Jun 19
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
1:03 pm - 4:55 pm
SJU
-
HVN
3h 52mnonstop
$180Avelo Airlines
Mon, Apr 27 - Sat, May 9
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$182Avelo Airlines
Mon, Jun 1 - Fri, 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
$190Avelo Airlines
Fri, Jun 5 - Fri, 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
$191Avelo Airlines
Mon, Jun 8 - Sat, Jun 13
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$193Avelo Airlines
Fri, Sep 18 - Fri, Sep 25
Avelo Airlines Logo
6:30 am - 10:27 am
HVN
-
SJU
3h 57mnonstop
Avelo Airlines Logo
11:38 am - 3:45 pm
SJU
-
HVN
4h 07mnonstop
$200Avelo Airlines
Mon, Jun 1 - Sat, Jun 6
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$201Avelo Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
6:30 am - 4:15 pm
HVN
-
STT
9h 45m
1 stop
Multiple Airlines Logo
5:10 pm - 1:11 pm
STT
-
HVN
20h 01m
2 stops
$434Multiple Airlines
Wed, Apr 22 - Sun, Apr 26
Multiple Airlines Logo
6:30 am - 4:15 pm
HVN
-
STT
9h 45m
1 stop
Multiple Airlines Logo
10:49 am - 3:15 pm
STT
-
HVN
28h 26m
3 stops
$445Multiple Airlines
Booking Insights

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

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

What is the cheapest New Haven to Caribbean flight route?

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

The cheapest ticket to Caribbean from New Haven found in the last 72 hours was to San Juan, at $215 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 $215.

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

The average price for all round-trip flights from New Haven to Caribbean 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 is generally in the afternoon, when round-trip flights cost $208 on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $313.

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

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, 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 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?

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

For New Haven to Caribbean, Sunday is the cheapest day to fly on average and Friday is the most expensive. Flying from Caribbean back to New Haven, the best deals are generally found on Friday, with Saturday being the most expensive.

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

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, 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, you should book around 4 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$103
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from New Haven to San Juan

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New Haven to Caribbean 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?

    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 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?

    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 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

  • 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 $216 one-way - $263 round-trip

Reviews of the top 3 airlines serving from New Haven to Caribbean

 
Need help choosing which airline to fly with from New Haven to Caribbean? 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.
7.6
Avelo AirlinesOverall score based on 88 reviews
8.3Crew
5.0Entertainment
5.1Food
7.1Comfort
7.7Boarding
Airline reviews

Flight was smooth. We boarded early and left Grand Rapids about a half hour ahead of schedule. We then arrived in Lakeland about 40 minutes early. Flights attendants (3) were welcoming and pleasant. Wish we would have at least been offered to buy a bottle of water. No beverage service at all.

8.0 ExcellentFamily, Jan 2026
GRR - LAL
Read more Avelo Airlines reviews

Flight was smooth. We boarded early and left Grand Rapids about a half hour ahead of schedule. We then arrived in Lakeland about 40 minutes early. Flights attendants (3) were welcoming and pleasant. Wish we would have at least been offered to buy a bottle of water. No beverage service at all.

I really liked the young man who checked me in and took my bags! He was so kind and was very helpful! I told my sister about the great service and him and she said that is why she flies Avelo Air.

The flight was delayed by a lot and the seats are pretty tight

Surprisingly was one of the better flights I’ve been on

Short 2-hour flight, we took off on time, ETA was earlier than stated, no interaction needed with stewards, no food, no entertainment on such a short flight.

Avelo provided exactly what I expected. They are a low-cost option with no frills but the experience was comfortable and the staff was great! I will be using them in the future for trips when cost is a priority for me.

Expect nothing and you will be fine. Seats are crammed.

Terrible landing. Uncomfortable seats. Great cabin crew-helpful and pleasant!

Tight fit in middle seat but OK for short flight. Crew was more interested in talking to each other than helping passengers - strickingly dissappointing. DAB is a great airport. New Haven sucks! Excellent value for the .

Avelo is definitely a budget airline and you get what you pay for. The plane was packed and the seats were not particularly comfortable. Staff was very nice and both of our flights were on time. The one thing I wish I had known was that the staff does not show up at the airport desk to check your bags until two hours before the flight. We had a 4:30 flight and had to check out of our hotel at noon. Since we have lounge passes we planned to check our bag, go through security and hang out at the lounge until we had to board. But because we could not check our bag until 2:30, when the staff showed up, we could not go through security and access the lounge. Passengers with boarding passes and carry on luggage would not have this issue. I might fly Avelo again but would only do carry on or plan to get to the airport no sooner than two hours before check in. And I would not recommend a long flight on Avelo since there is no food or entertainment and the seats are not comfortable.

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports