$111 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 9/21. 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$792
Montego Bay
Montego Bay2 stops$848
Oranjestad
Oranjestad2 stops$946
Nassau
Nassau2 stops$655
Punta Cana
Punta Cana1 stop$792
Montego Bay
Montego Bay2 stops$848
Oranjestad
Oranjestad2 stops$946
Nassau
Nassau2 stops$655

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, 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
$267Avelo 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
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
$282Avelo 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
$291Avelo Airlines
Fri, Sep 11 - Mon, Sep 14
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
$299Avelo Airlines
Fri, Sep 18 - Mon, Sep 28
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
$306Avelo Airlines
Mon, Aug 24 - Sun, Aug 30
Multiple Airlines Logo
6:55 pm - 12:56 am
HVN
-
SJU
30h 01m
2 stops
Multiple Airlines Logo
7:00 am - 5:46 pm
SJU
-
HVN
10h 46m
1 stop
$313Multiple Airlines
Fri, Oct 2 - Mon, Oct 5
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
$321Avelo Airlines
Thu, Jul 23 - Thu, Sep 10
Multiple Airlines Logo
6:31 pm - 2:00 pm
HVN
-
SJU
19h 29m
1 stop
Multiple Airlines Logo
8:30 am - 11:30 am
SJU
-
HVN
27h 00m
1 stop
$330Multiple 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
$334Avelo 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 $149 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 $149.

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 $339.

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, Monday is the cheapest day to fly on average and Wednesday 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 23 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$111
Best time to beat the crowds but there is an average 14% increase 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 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 - $323 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 85 reviews
8.2Crew
5.0Entertainment
7.1Comfort
5.1Food
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.

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

A nightmare. Scheduled flight delayed 2 hours then cancelled because pilot timed out . Unable to find another pilot. Really?! Weather certainly a factor, but JetBlue seemed totally unprepared for the chaos that ensued when flight routes were cancelled. More cancelled flights, finally many of us who had been bumped from other flights were allowed to board a Boston bound plane around 3:00am, delay after delay, sat on tarmac for another half hour while pilot dealt with weight distribution issues (?), arrived in Boston 4:30. Crew were wonderful- same attendants all day and night and they were exhausted. Fortunately for me and my son that Boston was our final destination, not so lucky for many who missed connecting flights.

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

The food took two hours to be delivered to my seat, when I'm on an overnight flight I want to sleep asap after take off

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

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

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

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports