$135 Find Cheap Flights from New Haven to Caribbean Islands

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 Islands departing on 5/28. 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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KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from New Haven to Caribbean Islands, as well as popular online travel agencies
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Flights Deals

Best Caribbean Islands Flight Deals from New Haven

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$659
Montego Bay
Montego Bay2 stops$472
Nassau
Nassau1 stop$383
Port of Spain
Port of Spain1 stop$688
Punta Cana
Punta Cana1 stop$659
Montego Bay
Montego Bay2 stops$472
Nassau
Nassau1 stop$383
Port of Spain
Port of Spain1 stop$688

Cheap Flights from New Haven to Caribbean Islands

 
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 Islands 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.

Recent round-trip flight deals from New Haven to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from New Haven to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
Avelo Airlines Logo
6:30 am - 10:15 amHVN-SJU
3h 45mnonstop
Avelo Airlines Logo
11:41 am - 3:44 pmSJU-HVN
4h 03mnonstop
$264Avelo Airlines
Find Deal
Wed, Jun 4 - Wed, Jun 11
Avelo Airlines Logo
7:00 am - 10:46 amHVN-SJU
3h 46mnonstop
Avelo Airlines Logo
11:41 am - 3:44 pmSJU-HVN
4h 03mnonstop
$289Avelo Airlines
Find Deal
Sat, Jun 14 - Sat, Jun 21
Avelo Airlines Logo
6:30 am - 10:15 amHVN-SJU
3h 45mnonstop
Avelo Airlines Logo
11:15 am - 3:20 pmSJU-HVN
4h 05mnonstop
$293Avelo Airlines
Find Deal
Wed, May 28 - Wed, Jun 4
Avelo Airlines Logo
6:30 am - 10:15 amHVN-SJU
3h 45mnonstop
Avelo Airlines Logo
11:15 am - 3:20 pmSJU-HVN
4h 05mnonstop
$315Avelo Airlines
Find Deal
Wed, May 14 - Sat, May 17
Avelo Airlines Logo
6:30 am - 10:16 amHVN-SJU
3h 46mnonstop
Avelo Airlines Logo
11:41 am - 3:44 pmSJU-HVN
4h 03mnonstop
$322Avelo Airlines
Find Deal
Mon, Aug 18 - Sat, Aug 23
 Logo
7:30 am - 10:38 pmHVN-SJU
15h 08m2 stops
 Logo
11:41 am - 3:44 pmSJU-HVN
4h 03mnonstop
Wed, Jun 4 - Wed, Jun 11
 Logo
6:30 am - 10:15 amHVN-SJU
3h 45mnonstop
 Logo
1:39 pm - 12:38 pmSJU-HVN
22h 59m1 stop
Wed, Jun 4 - Wed, Jun 11
 Logo
3:50 pm - 7:07 pmHVN-SJU
27h 17m1 stop
 Logo
8:12 pm - 10:28 pmSJU-HVN
26h 16m2 stops
Thu, May 15 - Mon, May 19
 Logo
3:50 pm - 7:07 pmHVN-SJU
27h 17m1 stop
 Logo
1:59 am - 6:54 pmSJU-HVN
16h 55m2 stops
Thu, May 15 - Sun, May 18
 Logo
3:50 pm - 7:07 pmHVN-SJU
27h 17m1 stop
 Logo
1:59 am - 10:04 pmSJU-HVN
20h 05m1 stop
Thu, May 15 - Sun, May 18
Useful Info

KAYAK's insights & trends for New Haven to Caribbean Islands flights

Get data-powered insights and trends into flights from New Haven to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest New Haven to Caribbean Islands flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from New Haven to Caribbean Islands.

The cheapest ticket to Caribbean Islands 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 month to fly from New Haven to Caribbean Islands?

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 Islands, 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 Islands is September, when tickets cost $205 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $551 and $384 respectively.

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

The average price of all round-trip flights from New Haven to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from New Haven to Caribbean Islands, look for departures on Mondays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Caribbean Islands, Monday is the cheapest day to fly and Wednesday is the most expensive.

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

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 Islands, 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 Islands, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 10 weeks before departure.


Good to know

Low seasonSeptember
High seasonMarch
Cheapest flight$135
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from New Haven to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from New Haven to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from New Haven to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from New Haven to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the evening, when round-trip flights cost $170 on average. Morning departures are around 65% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $322.

Top tips for finding cheap flights to Caribbean Islands

  • 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 $106 one-way - $240 round-trip

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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