$75 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 9/2. 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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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 5 days
Punta Cana
Punta Cana2 stops$700
Montego Bay
Montego Bay2 stops$666
Oranjestad
Oranjestad2 stops$1,252
Nassau
Nassau3 stops$495
Punta Cana
Punta Cana2 stops$700
Montego Bay
Montego Bay2 stops$666
Oranjestad
Oranjestad2 stops$1,252
Nassau
Nassau3 stops$495
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 $147 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 $147.

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 $187 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 $370.

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 July, when the average cost of round-trip tickets is $665 and $415 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 5 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

September

Cheapest flight

$75
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 3% 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 6:00 am and most flights take off in the morning. Each week, there are 4 flights.

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 85 reviews
7.1Comfort
8.2Crew
5.1Food
5.0Entertainment
7.7Boarding
Airline reviews

Packed old plane with uncomfortable seats. Great crew, especially Tara who was helpful to many. No water offered. Hard landing. Discount pricing is the benefit!

8.0 ExcellentMaurice, Aug 2026
Read more Avelo Airlines reviews

Packed old plane with uncomfortable seats. Great crew, especially Tara who was helpful to many. No water offered. Hard landing. Discount pricing is the benefit!

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!

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.

It was my first time in Jetblue flight in 10+ years(?) and the experience was horrible. You were better before. There were ATC delays sitting/waiting in the tarmac for 2 hours, I understand that this isn't Jetblue's problem but how the matter was handled poorly is. Cabin was so warm and hot couldn't get it to cool down for the entire waiting period worse, even during cruise flight. Start, the passengers were spoken to and treated like a little children with no respect. Constant/multiple annoying tone/voice PA announcements of mentioning "... only big/large suitcases are for the bin and small ones need to be placed under the seat, etc,..." I see that flight was delayed and crew were trying to get the plane ready to board as soon as they can but the way they presented was lack of better word, condesending and scolding tone to cattle. It was definite unpleasant, unwelcoming flight experience I have ever had with Jetblue. Whatever happen to smiles and fun employees , pleasant/helpful gate agents, flight attendants, crews, where have they gone? It was dissapointing flight experience overall from everyone. Sorry for the direct transparency.

Flight was cancelled as JetBlue could not find a pilot. Communication was poor and they did nothing for stranded passengers. Flight they rebooked us on was 4 days out.

JetBlue cancelled the flight. We had to rebook on another airline.

JetBlue cancelled the flight along with hundreds of others, for no apparent reason. no recourse, no rebooking options. never booking with them again

Jet Blue cancelled my flight after I had boarded. They attempted to rebook me for a new flight two days later. I was able to rebook with a different airline, but not until the next morning. As such, I was forced to get an expensive hotel and missed important work meetings Monday morning. I am very disappointed with the customer service and will be pursuing full reimbursement for my hotel cost.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

They cancelled the flight after 5 hours at the airport and the only flight they offered was for the next day with a 7.5 layover in fll. This was not going to work for me as this was only a weekend trip and getting into providence at 10 pm a day later caused me to lose Mo ey on hotels money on airport parking a dog sitter etc. they wouldn’t offer any type of a voucher or anything else. All they did was refund the flight which didn’t help me with all the money in time I lost. I was going to see my very sick father

The flight was on time the crew was courteous that makes for a good flight.

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

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

Frontier is good until they cancel your flight. Way too many cancellations.

I know Frontier is a “no-frills” airline. I understand the concept. However, I jumped on some tickets for our family vacation, expecting to play a bit of a game to figure out the family bags and not over spend. In the end, I got the short end of this deal by far. 1. I did not expect them to charge the baggage fee for each direction. It makes the fee look high-ish at a glance, but reasonable. Then when you get to checkout and realize you have to pay it twice to come home with your luggage, it becomes ridiculous. 2. The low checked bag weight limit. I am used to packing a 50lb bag with my preferred airline. Frontier’s artificially low 40lb limit more quickly triggers the extra weight fee, which almost DOUBLES the price of the bag if you go over ($79 for the bag/$75 for the next 10 lbs) 3. The fee for a carry-on bag is the same as a checked bag but with a lower size and weight limit. Make it make sense! 4. The seats are terrible. My 2.5 hour flight almost had me losing my mind. I’m 6’3” and my femurs barely fit in the space provided. My knees had to wiggle just right to jam into the crack next to the armrest of the seat in front of me. The cushioning was thin and inadequate. I am tall but I’m not a freak. These seats are unacceptable. 5. I overheard the woman next to me speaking with the gate agent about being charged a $25 fee for not checking in online - she checked in at the airport counter when she arrived. That’s ridiculous. She was old and in a wheelchair. She had a paper boarding pass, and was obviously not tech savvy. She should not be punished for that. 6. They do not have good placement in the terminals. It was always out on the end or down on a subfloor, and we had to walk out on the tarmac almost every time. In Denver. Their home airport! 7. Every time I loaded a new page on the website while buying my tickets or my bags, it was constantly trying to upsell me on some esoteric bundle. Like, a pop-up every time. Very annoying. 8. No screens in the boarding area (at least where we were) to confirm you’re in the right place. Just static gate number signs. I am sure these are standard practices for Frontier, and I should have read more about them before I purchased tickets, but as a result of this single round trip, I do not plan to ever use this cut-rate airline again. I would rather pay the normal amount for a ticket and be treated like a customer instead of a mark.

Our flight was delayed 2 hours and when they changed the the time to 1 hour I wasn't alerted and when I checked the gate the plane was still there but they already shut the doors so I had to buy another flight.

Great except upon arrival it took them a long time to open the doors

Frontier feels like a family I Worked for Eastern Airlines back in the day and I felt the family vibe that I had then. Thank you

Terrible. Delayed my family flight for several hours affecting family plans

During the flight I suddenly felt very sick, and no one from the crew even tried to help me or check on my condition. They seemed completely indifferent and showed no concern for my well-being. I was very disappointed by the lack of care and compassion. I hope the airline improves its customer service and trains its crew to respond better when passengers need assistance.

Tiny seats, no entertainment, no amenities, delays, they charge for carry on and their allowed personal item is smaller than in other airlines.

The seats are tiny and they don’t recline. The planes are dirty and very small. You have to pay for carry on and even the personal item that you’re allowed is smaller than with other airlines. Flights are usually delayed and there’s no screens or any amenities or entertainment.

Flight was delayed but it was very smooth. Crew was very nice. Seats are uncomfortable but ok.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports