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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 Cana1 stop$618
Montego Bay
Montego Bay2 stops$784
Oranjestad
Oranjestad2 stops$1,628
Nassau
Nassau1 stop$592
Kingston
Kingston2 stops$1,616
Simpson Bay
Simpson Bay1 stop$1,211
Providenciales
Providenciales1 stop$781
Punta Cana
Punta Cana1 stop$618
Montego Bay
Montego Bay2 stops$784
Oranjestad
Oranjestad2 stops$1,628
Nassau
Nassau1 stop$592
Kingston
Kingston2 stops$1,616
Simpson Bay
Simpson Bay1 stop$1,211
Providenciales
Providenciales1 stop$781
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?

The cheapest ticket to Caribbean from New Haven found in the last 5 days was to San Juan, at $151 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 $151.

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

The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $220 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 $339.

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

The cheapest month for flights from New Haven to Caribbean is November, when tickets cost $258 (return) on average. On the other hand, the most expensive months are July and December, when the average cost of round-trip tickets is $415 and $410 respectively.

What’s the cheapest day of the week to fly from New Haven to Caribbean?

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 Friday, with Monday being the most expensive.

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

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 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.

Good to know

Low season

October
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 2% increase in price.

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 52m. The most common departure time is 6:00 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 $84 one-way - $169 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 87 reviews
4.9Entertainment
5.0Food
8.2Crew
7.1Comfort
7.8Boarding
Airline reviews

Flight boarding was easy & fast in HVN using both doors front & back. Ample space for carryon overhead bin & personal item underseat. Basic flight, no food, drink or entertainment offered, but short direct flight arrived safely on time. Right product for good price.

10.0 ExcellentLisa, Oct 2026
Read more Avelo Airlines reviews

Flight boarding was easy & fast in HVN using both doors front & back. Ample space for carryon overhead bin & personal item underseat. Basic flight, no food, drink or entertainment offered, but short direct flight arrived safely on time. Right product for good price.

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.

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.

The boarding agent and checked bag agent were both rude. It only takes a second to be kind. However, the flight crew was amazing. I got a turkey sandwich and it wasn't bad---not great but not bad. The internet was my biggest problem. This was a work trip and I REALLY needed the internet to meet a deadline but it didn't work for 80% of the trip. Very disappointing.

I tried to check in beforehand from Ireland. The Jet Blue website sent me to the Aer Lingus website and vice versa. I tried to get a boarding pass at Dublin Airport as well, but they said they couldn't help me either. I had to wait until I arrived at the gate in Boston to secure a boarding pass...it was a bit nerve wracking.

Great flight. Best in years. Very clean craft. Easy boarding. Communicative pilot. Friendly flight attendants. Absolutely smooth take off, in flight and landing. Very comfortable seats. Smoothest flight I've experienced in years. THANK YOU JET BLUE!

I was asked to pony up an additional $239 (over the $735 paid originally) for a one way middle seat, which was very uncomfortable. Where did you expect me to sit?

Jet Blue sevice was good. Just don't understand why they charge for earphones to listen to flight entertainment. Other than that, everything was excellent.

Mostly good, flight take off in time and land earlier I can’t ask for more..

The crew was not nice this time. I asked for a drink one time and the girl didn’t say anything to me and just got me the hot drink while walking super fast to the back. We were sitting in the back and she wasn’t doing anything except socializing. She was upset I asked for something and she had to do her job. I also didn’t fully have it in my hands when she handed it to me so it was dangerous. She was abrupt and rude. She wouldn’t allow for people to spread out like previous flights we had been on if they were empty, and there were empty rows. It was strange and she enjoyed being angry at us.

The plane was FREEZING COLD. Like I was wishing I'd brought gloves. Is this how JetBlue sells more blankets? Other than that, all fine. Crew just as nice as usual. A flight attendant asked (who? The pilot?) to have the air turned down for a great number of passengers who were as cold as I was. They (again -- who is "they") did not.

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

THE BARE METAL SEATS AT THE FRONTIER GATE IN CLEVELAND HOPKINS AIRPORT ARE DISGUSTING...BUT JUST A LITTLE BETTER THAN THE SEAT MATERIALS ON THE PLANE! THE "COMMERCIAL" ANNOUNCMENT PUSHING THE CREDIT CARD DEAL IS OBNOXIOUS AND UNWELCOME! THE VOLUME OF THE OFFER ANNOUNCMENET BLARES LOUDLY AND IS FILLED WITH A HYPED UP, CANNED SCRIPT. BOTTOM LINE IS THE FLIGHT AND THE CREW WERE VERY GOOD EXCEPT FOR THE ABOVE.

Maximizing profits is one way to a healthy bottom line, the other is repeat business and referrals from satisfied customers. Frontier has clearly chosen the former. One of many examples: Family emergency required me to cut trip short. Headed to the airport to fly standby for the return trip I had already paid for (yes I understand prices vary with demand etc). Was told there is no standby and that I would need to pay for, despite what it's called by the company, what amounts to a new ticket. And surprise surprise, there turned out to be dozens of empty seats on that flight. To say nothing of the sleazy third and fourth party resellers, the flight/ticket insurance I elected and thought I had paid for that mysteriously wasn't there when I needed it before I left, and on and on with third world sleazy management decisions. The inflight coffee (that I had to pay for) was very good though.

You have to be super careful when purchasing as *everything*, a carryon or a sip of soda, has a fee. They relentlessly chip away at you with surcharges and extra costs … and it’s not always clear what you are getting when you buy your ticket. Will not fly them again. And … crew were not friendly until off boarding .. like they don’t like working for Frontier.

Air was off while waiting on the runway and the temperatures became very uncomfortably hot. Flight attendants were very loud and rude the entire flight.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation" for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy, and their reliability is non-existent. I will never fly Frontier again, and no one else should either if they actually need to get where they want to go. Tip for anyone flying from Denver to Cincinnati: Avoid Frontier connecting flights or layovers at all costs, especially for time-sensitive events. Book direct flights with an airline that actually offers reliable customer support and rebooking options when delays occur.

I booked tickets from San Diego to Cincinnati months in advance to attend my sister’s wedding, a wedding where I was serving as the officiant. At 10:00 PM the night before my 6:00 AM flight (just 8 hours before departure), I received an alert that my first leg to Denver was delayed, causing me to miss my connecting flight to Cincinnati. When I called Frontier customer service, they informed me that they couldn't get me on any other flight that would get me there in time for the Saturday wedding, let alone the rehearsal dinner. Because I had a critical role in the wedding, I was forced to buy a last-minute ticket on another airline for three times the original price, it costing me well over $1,000 extra. Even with the emergency flight, I still missed the rehearsal dinner entirely. When I spoke with Frontier, they agreed to refund my original ticket, but showed zero care or accountability for the massive financial burden and distress they caused. Their "compensation” for causing me to spend an extra $1,000+ and miss an irreplaceable family event? A $75 Frontier voucher. Frontier completely dropped the ball. Their customer service showed zero empathy letting me know that it was Frontier who was the real victim by refunding my ticket price, and their reliability is non-existent. I will never fly Frontier again, and I strongly advise anyone who actually needs to arrive at their destination on time for an important event to book with literally any other airline.

Flight delayed and missed connection. Next available flight was a 10 hour delay.

It got me to my destination? However we were an hour delayed departing, and we never received any updates or notifications from staff. Poor communication and customer service.

Frontier didn’t give us enough notice that our flight had been delayed. I was just entering the airport when I received the notice, less than 2hrs before my scheduled flight. They delayed it 1hr 22min because another jet left late out of Vegas. Frontier needs better communication with customers because I could have eaten at home and had someone drive me instead of paying for an Uber.

Great flight, no problems. I wish they would increase the checked bag weight limit. Packing was very stressful.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental