What airlines fly to Caribbean Islands?

JetBlue, Delta and Frontier are the top three most popular airlines that fly to Caribbean Islands from New Haven according to our data. JetBlue is the first choice among our users, with 61% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 13 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

How many flights depart from New Haven to Caribbean Islands on average per week?

2 flights are operational weekly from New Haven to Caribbean Islands as of April 2026. The most popular departure day for this route is Wed, with 50% of flights per week taking off on this day.

What is the cheapest airline that flies from Tweed-New Haven to Caribbean Islands?

Avelo Airlines and Breeze Airways are the most popular carriers operating from Tweed-New Haven to Caribbean Islands

When did momondo last update prices for flights from Tweed-New Haven Airport to Caribbean Islands?

Prices for flights from Tweed-New Haven Airport to Caribbean Islands were last updated today.

How many operators does momondo search for flights from Tweed-New Haven Airport to Caribbean Islands?

As of April 2026, there are 3 operators available to choose from for flights from Tweed-New Haven Airport to Caribbean Islands.

How old do you have to be to fly from Tweed-New Haven Airport to Caribbean Islands?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tweed-New Haven Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$111 Cheap Flights from New Haven to Caribbean Islands in 2026

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Find the cheapest flights from New Haven to Caribbean Islands

Round-trip

One-way

Last minute

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Cheap round-trip flights

Enter your travel dates to find the best prices.

8:00 am - 11:50 am

HVN

SJU

3h 50mnonstop

12:58 pm - 4:50 pm

SJU

HVN

3h 52mnonstop

$211Avelo Airlines

Mon, May 18 - Fri, May 29

8:00 am - 11:50 am

HVN

SJU

3h 50mnonstop

12:58 pm - 4:50 pm

SJU

HVN

3h 52mnonstop

$213Avelo Airlines

Mon, May 18 - Fri, May 29

6:30 am - 10:27 am

HVN

SJU

3h 57mnonstop

11:38 am - 3:45 pm

SJU

HVN

4h 07mnonstop

$236Avelo Airlines

Fri, Sep 11 - Fri, Sep 18

7:00 am - 10:50 am

HVN

SJU

3h 50mnonstop

12:05 pm - 3:57 pm

SJU

HVN

3h 52mnonstop

$245Avelo Airlines

Wed, May 13 - Wed, May 20

6:30 am - 10:27 am

HVN

SJU

3h 57mnonstop

11:38 am - 3:45 pm

SJU

HVN

4h 07mnonstop

$252Avelo Airlines

Fri, Sep 11 - Fri, Sep 18

7:00 am - 10:50 am

HVN

SJU

3h 50mnonstop

12:05 pm - 3:57 pm

SJU

HVN

3h 52mnonstop

$265Avelo Airlines

Sat, May 16 - Wed, May 20

7:00 am - 10:50 am

HVN

SJU

3h 50mnonstop

12:58 pm - 4:50 pm

SJU

HVN

3h 52mnonstop

$267Avelo Airlines

Sat, May 16 - Fri, May 29

7:00 am - 10:50 am

HVN

SJU

3h 50mnonstop

12:58 pm - 4:50 pm

SJU

HVN

3h 52mnonstop

$272Avelo Airlines

Wed, Jun 10 - Fri, Jun 12

5:00 pm - 12:31 pm

HVN

MBJ

20h 31m

2 stops

1:05 pm - 12:35 pm

MBJ

HVN

22h 30m

3 stops

$624Multiple Airlines

Sat, Jun 13 - Sat, Jun 20

6:55 pm - 10:20 am

HVN

PUJ

15h 25m

1 stop

8:11 pm - 6:15 pm

PUJ

HVN

22h 04m

2 stops

$1,084Breeze Airways

Fri, Aug 14 - Sun, Aug 16

Avelo Airlines flights from New Haven to Caribbean Islands

Our best Avelo Airlines deals on New Haven to Caribbean Islands flight tickets

Avelo Airlines

May 18

HVN8:00 amTweed-New Haven

3h 50m

SJU11:50 amSan Juan Luis Munoz Marin Intl

May 29

SJU12:58 pmSan Juan Luis Munoz Marin Intl

3h 52m

HVN4:50 pmTweed-New Haven

$211

Avelo Airlines

May 18

HVN8:00 amTweed-New Haven

3h 50m

SJU11:50 amSan Juan Luis Munoz Marin Intl

May 29

SJU12:58 pmSan Juan Luis Munoz Marin Intl

3h 52m

HVN4:50 pmTweed-New Haven

$213

Avelo Airlines

Sep 11

HVN6:30 amTweed-New Haven

3h 57m

SJU10:27 amSan Juan Luis Munoz Marin Intl

Sep 18

SJU11:38 amSan Juan Luis Munoz Marin Intl

4h 07m

HVN3:45 pmTweed-New Haven

$236

momondo Fare Finder

Use the filters below to find and compare flights from New Haven to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Quickest round-trip

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 5/18

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/29

12:58 pm-4:50 pm

Nonstop3h 52m

$211

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 5/18

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/29

12:58 pm-4:50 pm

Nonstop3h 52m

$213

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 9/11

6:30 am-10:27 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Fri 9/18

11:38 am-3:45 pm

Nonstop4h 07m

$236

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 5/13

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/20

12:05 pm-3:57 pm

Nonstop3h 52m

$245

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 9/11

6:30 am-10:27 am

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Fri 9/18

11:38 am-3:45 pm

Nonstop4h 07m

$252

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/16

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/20

12:05 pm-3:57 pm

Nonstop3h 52m

$265

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/16

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 5/29

12:58 pm-4:50 pm

Nonstop3h 52m

$267

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 6/10

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 6/12

12:58 pm-4:50 pm

Nonstop3h 52m

$272

New HavenMontego Bay

HVN - MBJ

HVNMBJ

Tweed-New Haven

Sat 6/13

5:00 pm-12:31 pm

2 stops20h 31m

Montego Bay Sangster Intl

Sat 6/20

1:05 pm-12:35 pm

3 stops22h 30m

$624

New HavenPunta Cana

HVN - PUJ

HVNPUJ

Tweed-New Haven

Fri 8/14

6:55 pm-10:20 am

1 stop15h 25m

Punta Cana

Sun 8/16

8:11 pm-6:15 pm

2 stops22h 04m

$1,084

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from New Haven to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from New Haven to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $208. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $366. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from New Haven to Caribbean Islands at noon for as low as $208. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $322. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

Fly from Tweed-New Haven to San Juan Luis Munoz Marin Intl for the best Tweed-New Haven - Caribbean Islands flight prices

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

You are more likely to see cheaper flights to Caribbean Islands from New Haven when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $325 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from New Haven for as low as $269 on momondo.

Can stopping save me money on New Haven to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between New Haven to Caribbean Islands.

Cheap New Haven to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from New Haven to Caribbean Islands

Fastest flight time	3h 50m
Direct flights	Tue, Thu, Sat and Sun
Airports in Caribbean Islands	99 airports

The fastest flight from New Haven to Caribbean Islands takes 3h 50m

Direct flights go from New Haven to Caribbean Islands on Tuesday, Thursday, Saturday and Sunday. There are no airlines offering direct flights.

There are 99 airports in Caribbean Islands. From New Haven there are direct flights to San Juan Luis Munoz Marin Intl (SJU).

Search flight deals

Frequently asked questions about flying from New Haven to Caribbean Islands

When did momondo last update prices for flights from Tweed-New Haven Airport to Caribbean Islands?
Prices for flights from Tweed-New Haven Airport to Caribbean Islands were last updated today.
How many operators does momondo search for flights from Tweed-New Haven Airport to Caribbean Islands?
As of April 2026, there are 3 operators available to choose from for flights from Tweed-New Haven Airport to Caribbean Islands.
How old do you have to be to fly from Tweed-New Haven Airport to Caribbean Islands?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tweed-New Haven Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The travel and health documents required for your trip to Caribbean Islands can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean Islands. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from New Haven to Caribbean Islands?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from New Haven to Caribbean Islands is Boeing 737-800 Passenger/BBJ2 (winglets) (29.25% of total bookings). The next most popular plane models are Airbus A220-300 (26.08%), Airbus A320-100/200 (13.05%), and Airbus A321neo (7.41%).

Best airlines flying from New Haven to Caribbean Islands

Compare and see reviews for airlines that fly from New Haven to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $135	Free Cancellation	Rating 5.6 2,969 reviews	Search Frontier flights
Avelo Airlines	PriceFrom $163	Free Cancellation	Rating 7.6 88 reviews	Search Avelo Airlines flights
JetBlue	PriceFrom $207	Free Cancellation	Rating 7.1 2,968 reviews	Search JetBlue flights

Why use momondo?

Why should I use momondo to find a flight deal from New Haven to Caribbean Islands?

Finding the right flight to Caribbean Islands from New Haven is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

Can I find flights from New Haven to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for New Haven to Caribbean Islands flights to just show those with flexible booking policies.

How can momondo help me find flights from New Haven to Caribbean Islands?

Once all potential New Haven to Caribbean Islands flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from New Haven to Caribbean Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of New Haven to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.