$159 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 5/30. 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

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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 Cana1 stop$653
Montego Bay
Montego Bay2 stops$770
Nassau
Nassau2 stops$588
Kingston
Kingston3 stops$1,439
Punta Cana
Punta Cana1 stop$653
Montego Bay
Montego Bay2 stops$770
Nassau
Nassau2 stops$588
Kingston
Kingston3 stops$1,439

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

Fri, Aug 28 - Fri, Sep 4
Avelo Airlines Logo
6:30 am - 10:20 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$220Avelo Airlines
Mon, Aug 31 - Mon, Sep 7
Avelo Airlines Logo
6:30 am - 10:20 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:08 pm - 4:15 pm
SJU
-
HVN
4h 07mnonstop
$235Avelo 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
$245Avelo Airlines
Mon, Jun 8 - 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
$250Avelo Airlines
Mon, Jun 8 - 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
$263Avelo 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
$266Avelo Airlines
Fri, Sep 4 - Mon, Sep 7
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
$269Avelo 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
$272Avelo Airlines
Mon, Jun 15 - Sun, Jun 21
Multiple Airlines Logo
6:31 pm - 2:45 pm
HVN
-
NAS
20h 14m
2 stops
Multiple Airlines Logo
12:00 pm - 7:56 pm
NAS
-
HVN
7h 56m
1 stop
$588Multiple Airlines
Thu, Jul 30 - Mon, Aug 3
Multiple Airlines Logo
5:27 pm - 8:55 am
HVN
-
NAS
15h 28m
2 stops
Multiple Airlines Logo
12:00 pm - 2:02 pm
NAS
-
HVN
26h 02m
1 stop
$624Multiple 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 $168 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 $168.

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 $317.

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 September and April, when the average cost of round-trip tickets is $260 and $182 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 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$154
Best time to beat the crowds with an average 16% 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 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.

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
7.1Comfort
5.1Food
7.7Boarding
8.3Crew
5.0Entertainment
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.

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

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

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports