$82 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 2/12. 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

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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$442
Montego Bay
Montego Bay1 stop$557
Oranjestad
Oranjestad2 stops$612
Nassau
Nassau1 stop$493
St. John's
St. John's2 stops$795
Punta Cana
Punta Cana3 stops$442
Montego Bay
Montego Bay1 stop$557
Oranjestad
Oranjestad2 stops$612
Nassau
Nassau1 stop$493
St. John's
St. John's2 stops$795

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

Thu, Feb 12 - Sun, Feb 15
Avelo Airlines Logo
8:59 pm - 1:49 amHVN-SJU
3h 50mnonstop
Avelo Airlines Logo
3:40 am - 6:45 amSJU-HVN
4h 05mnonstop
$201Avelo Airlines
Find Deal
Thu, Feb 12 - Thu, Feb 19
Avelo Airlines Logo
8:59 pm - 1:49 amHVN-SJU
3h 50mnonstop
Avelo Airlines Logo
3:40 am - 6:45 amSJU-HVN
4h 05mnonstop
$202Avelo Airlines
Find Deal
Sun, Mar 1 - Sat, Mar 7
Avelo Airlines Logo
8:59 pm - 1:49 amHVN-SJU
3h 50mnonstop
Avelo Airlines Logo
12:20 pm - 3:25 pmSJU-HVN
4h 05mnonstop
$203Avelo Airlines
Find Deal
Wed, Nov 12 - Tue, Nov 25
Avelo Airlines Logo
2:00 pm - 6:54 pmHVN-SJU
3h 54mnonstop
Avelo Airlines Logo
3:44 am - 6:45 amSJU-HVN
4h 01mnonstop
$206Avelo Airlines
Find Deal
Sat, Nov 15 - Wed, Nov 19
Avelo Airlines Logo
2:00 pm - 6:54 pmHVN-SJU
3h 54mnonstop
Avelo Airlines Logo
1:24 pm - 4:25 pmSJU-HVN
4h 01mnonstop
$210Avelo Airlines
Find Deal
Mon, Dec 8 - Wed, Dec 17
Avelo Airlines Logo
2:11 pm - 7:05 pmHVN-SJU
3h 54mnonstop
Avelo Airlines Logo
1:24 pm - 4:25 pmSJU-HVN
4h 01mnonstop
$216Avelo Airlines
Find Deal
Sun, Mar 8 - Sun, Mar 22
Avelo Airlines Logo
8:59 pm - 12:49 amHVN-SJU
3h 50mnonstop
Avelo Airlines Logo
2:40 am - 6:45 amSJU-HVN
4h 05mnonstop
$218Avelo Airlines
Find Deal
Wed, Nov 12 - Wed, Nov 26
Avelo Airlines Logo
2:00 pm - 6:54 pmHVN-SJU
3h 54mnonstop
Avelo Airlines Logo
1:24 pm - 4:25 pmSJU-HVN
4h 01mnonstop
$222Avelo Airlines
Find Deal
Fri, Nov 21 - Sun, Nov 23
Multiple Airlines Logo
4:15 pm - 10:49 amHVN-SJU
17h 34m1 stop
Multiple Airlines Logo
3:44 am - 6:45 amSJU-HVN
4h 01mnonstop
$305Multiple Airlines
Find Deal
Sat, Feb 7 - Wed, Feb 11
Multiple Airlines Logo
8:00 am - 7:21 pmHVN-SJU
10h 21m1 stop
Multiple Airlines Logo
12:20 pm - 3:25 pmSJU-HVN
4h 05mnonstop
$307Multiple Airlines
Find Deal
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 $122 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 $122.

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 $212 (return) on average. On the other hand, the most expensive months are December and February, when the average cost of round-trip tickets is $650 and $412 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 Saturday 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 5 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$82
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 19% 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.

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

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $170 on average. Morning departures are around 67% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $296.

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 $132 one-way - $363 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 82 reviews
8.2Crew
7.7Boarding
5.0Food
7.1Comfort
5.0Entertainment
Airline reviews

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.

10.0 ExcellentChristina, Sep 2025EUG - BUR
Read more Avelo Airlines reviews

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.

No food or entertainment, but flight very comfortable and on time.

Baggage claim was barbaric at Wilmington. I realize that this is a startup airline but if they hope to grow or even survive they need to upgrade this airport. There is no automated luggage carousel and at times you are not only fighting your fellow passengers to get to your bags but also passengers coming in from other flights who cross right in front of you

No frills, i.e., no drinks or snacks. One is charged for everything. The cost really adds up. The crew and flight attendants were excellent and very pleasant.

I always walk by a pallet of Avelo branded mini bottles of water on the tarmac, but I’ve never seen them in flight. Yup, not even water offered on a 3 hour flight. No wi-fi onboard. We just watch the flight crew on their phone for 3 hours every flight. At least a mid-flight trash pickup would be great. Better than my last flight, but they only could have gone up from there. Don’t use for business or ticketed vacation like Disney… too unreliable.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everyone seemed to be in zone 1 for boarding. Maybe break it up a little. Otherwise, smooth flight.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

I think Frontier was very good at communication. Their app worked very well. Loading was great and the flight was nice and easy.

This airline sucks. They offer low rates then charge you for everything, the app does not work well, the seats are the most uncomfortable. Maintenance issues on the flight, and you still have to sit through their credit card commercials. People are nice enough but does not make up for overall poor experience.

Everything you need to know for your flight to Caribbean

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