$107 Find Cheap Flights from New Haven to Caribbean - 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 departing on 9/1. 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.
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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 Cana3 stops$803
Montego Bay
Montego Bay2 stops$1,159
Oranjestad
Oranjestad2 stops$1,343
Nassau
Nassau1 stop$642
Simpson Bay
Simpson Bay2 stops$1,084
Punta Cana
Punta Cana3 stops$803
Montego Bay
Montego Bay2 stops$1,159
Oranjestad
Oranjestad2 stops$1,343
Nassau
Nassau1 stop$642
Simpson Bay
Simpson Bay2 stops$1,084

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

Wed, Oct 7 - Wed, Oct 14
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
7:00 pm - 10:57 pm
SJU
-
HVN
3h 57mnonstop
$243Avelo Airlines
Wed, Sep 23 - Fri, Sep 25
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$245Avelo Airlines
Sat, Aug 22 - Wed, Aug 26
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
7:00 pm - 10:57 pm
SJU
-
HVN
3h 57mnonstop
$253Avelo Airlines
Wed, Aug 26 - Wed, Sep 2
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
7:00 pm - 10:57 pm
SJU
-
HVN
3h 57mnonstop
$258Avelo Airlines
Sat, Aug 29 - Sat, Sep 5
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
7:00 pm - 10:57 pm
SJU
-
HVN
3h 57mnonstop
$260Avelo Airlines
Sat, Oct 10 - Sat, Oct 17
Avelo Airlines Logo
2:10 pm - 6:00 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
7:00 pm - 10:57 pm
SJU
-
HVN
3h 57mnonstop
$268Avelo 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
$275Avelo Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
5:27 pm - 12:56 am
HVN
-
SJU
31h 29m
2 stops
Multiple Airlines Logo
8:57 pm - 2:02 pm
SJU
-
HVN
17h 05m
1 stop
$280Multiple Airlines
Fri, Sep 4 - 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
$283Avelo Airlines
Tue, Aug 25 - Tue, Sep 1
Multiple Airlines Logo
2:47 pm - 4:15 pm
HVN
-
NAS
25h 28m
1 stop
Multiple Airlines Logo
12:00 pm - 2:57 pm
NAS
-
HVN
26h 57m
1 stop
$642Multiple 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 5 days was to San Juan, at $323 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 $323.

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 at night, which is peak travel time and where the average cost of a ticket is $347.

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 March, when tickets cost $78 (return) on average. On the other hand, the most expensive months are July and September, when the average cost of round-trip tickets is $264 and $260 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, Monday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Caribbean back to New Haven, the best deals are generally found on Monday, 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 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$107
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly and prices are also 4% lower on average.
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.

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

    There is a maximum of 1 nonstop flight a day that takes off from New Haven and lands in Caribbean, 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

  • 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 - $372 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.
7.5
Avelo AirlinesOverall score based on 84 reviews
7.1Comfort
5.1Food
5.0Entertainment
8.2Crew
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 .

Nightmare airline. Avoid Avelo. Understaffed at check-in with long, slow lines. Inexplicably had two flights and only one plane. Not weather or maintenance related apparently. One was supposed to go to Myrtle Beach and one to Orlando. I imagine someone thought it would be better to fly the available plane to Myrtle Beach and back and then go to Orlando since that round-trip was shorter. This didn’t account for the human factor of an end-of-week Orlando flight being 85% Disney passengers and putting the flight on a six-hour delay in New Haven airport… which, if you’ve been there, is tiny and has nothing to do for 50 kids excited to get to Disney. This delay was announced at the time of departure. No one realized before the time of departure there was no plane on the ground? And no one thought… hey I think the Myrtle Beach crowd might be a better one to have wait if we’re going to make a choice here (mind you the initial inbound plane was coming from Orlando and supposed to be out aircraft… they literally said let just grab this plane because it’s here to get this other group out at the last second). There is/was zero customer service desk for Avelo in HVN and there were no updates/announcements throughout the day. Plane still gets back late and we finally leave. No wi-fi on these planes, no snack or even water. I know this is budget airline, but expected at least a water after 8 hours of travel day. This should have been offered in terminal too. We land… hooray. Would you believe there is no ground crew to get the plane in to the gate… for 27 minutes. 27 minutes!!! At this point the rental car center is closing in 10 minutes, kids on the plane are crying again, and everyone is talking about how they’re never flying Avelo again. Finally get off. Bags are out at baggage claim right away (finally something right?), but they’ve stopped the carousel immediately and there is no baggage service rep. People are climbing over the carousel to get to the far side (if you’ve ever been to MCO you’ve seen it) because obviously they just stopped it immediately once all the bags were out. This airline is a dumpster fire. Icing on the cake was that while everyone was stuck in HVN, they were setting up for a celebration of their millionth passenger tomorrow. I bet 995,000 of those will never fly the airline again. Don’t fly Avelo. You’ve been warned.

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

We were several hours delayed due to confusion during boarding. Evidently the crew could not match the manifest with the boarded customers. After significant time trying to find individuals on board, a crew member walked through the entire plane re-scanning each of our boarding passes. Then we had to wait for a new slot to depart, and when we landed, our gate was not ready. It was a complete goat rodeo from start to finish.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Horrible. Flight was cancelled, jet blue app not working to rebook, no phone number available to call Jet Blue, 400 ish people in line for the help desk, stuck in Boston for 2 more days had to book new flight with a different airline and still not sure if I will be able to get any refund.

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

Separated a pair of family members(father and teenage daughter) on all legs of the flight that were booked together, just to create an upsell. Food was horrible and only catered to vegetarians and gluten free crowd. I’d rather give more of my money to another straight shooting airline.

Flight was delayed many times. The crew was friendly but you eleven had to buy headphones to access the movies in the plane. $8 is not a lot for one person but it is when you travel with all your family.

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

The flight was delayed after already taxiing from the gate due to a malfunction. After 3 hours we were told the flight was canceled. The next flight available was Sunday. My daughter and I stayed overnight in the airport due to this issue. I was given a $12 meal voucher. Unacceptable

The flight was great . But you only had one vegan item on the whole flight and someone prior to me took it . I was so disappointed cause I came in from the flooded area and couldn’t pick up anything prior to my flight .

I really didn't like anything. Paid for my checked luggage online ($79) and then was told that I would have to paid another $79 for my carry on. Was not allowed to enter the terminal until 3 hours before my flight and when I finally was allowed to check my bag and enter, my flight was delayed 3 times. When I finally landed, we were all instructed to "run off the plane" as they had to do a quick turn around to Las Vegas. Me and several of my flying companions will never fly Frontier again.

I paid for the upgraded bundle. Was worth it! Great experience round trip!

It was awful everything about it terrible I will never ever ever ride it again

It was awful ....my first time flying on it and I will NEVER fly it again ....everything about it was terrible .....most especially the flight attendants

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports