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Cheap flights from New Haven to Caribbean from $74

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from New Haven to Caribbean departing on 3/2. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$157Avelo Airlines
Wed, Apr 22 - Wed, Apr 29
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$188Avelo Airlines
Sat, May 9 - Wed, May 13
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$201Avelo Airlines
Sat, May 9 - Wed, May 20
Avelo Airlines Logo
8:00 am - 11:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
1:03 pm - 4:55 pm
SJU
-
HVN
3h 52mnonstop
$205Avelo Airlines
Mon, Jul 20 - Mon, Jul 27
Multiple Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Multiple Airlines Logo
7:00 am - 2:32 pm
SJU
-
HVN
7h 32m
1 stop
$237Multiple Airlines
Wed, Apr 22 - Wed, Apr 29
Avelo Airlines Logo
8:30 am - 1:20 pm
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
2:20 pm - 5:25 pm
SJU
-
HVN
4h 05mnonstop
$239Avelo Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
2:50 pm - 10:09 pm
HVN
-
SJU
7h 19m
1 stop
Multiple Airlines Logo
12:05 pm - 3:57 pm
SJU
-
HVN
3h 52mnonstop
$242Multiple Airlines
Sat, May 9 - Wed, May 13
Multiple Airlines Logo
8:44 pm - 10:09 am
HVN
-
SJU
12h 25m
1 stop
Multiple Airlines Logo
4:22 pm - 11:27 am
SJU
-
HVN
20h 05m
1 stop
$247Multiple Airlines
Sun, Mar 1 - Thu, Mar 5
Avelo Airlines Logo
7:00 am - 10:50 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:58 pm - 4:50 pm
SJU
-
HVN
3h 52mnonstop
$257Avelo Airlines
Wed, May 13 - Mon, May 18
Multiple Airlines Logo
2:50 pm - 10:09 pm
HVN
-
SJU
7h 19m
1 stop
Multiple Airlines Logo
7:00 am - 2:32 pm
SJU
-
HVN
7h 32m
1 stop
$266Multiple Airlines
Sat, May 9 - Wed, May 13

Avelo Airlines flights from New Haven to Caribbean

Our best Avelo Airlines deals on New Haven to Caribbean flight tickets
Avelo Airlines
Apr 22
HVN7:00 amTweed-New Haven
3h 50m
SJU10:50 amSan Juan Luis Munoz Marin Intl
Apr 29
SJU12:05 pmSan Juan Luis Munoz Marin Intl
3h 52m
HVN3:57 pmTweed-New Haven
$157
Avelo Airlines
May 9
HVN7:00 amTweed-New Haven
3h 50m
SJU10:50 amSan Juan Luis Munoz Marin Intl
May 13
SJU12:05 pmSan Juan Luis Munoz Marin Intl
3h 52m
HVN3:57 pmTweed-New Haven
$188
Avelo Airlines
May 9
HVN7:00 amTweed-New Haven
3h 50m
SJU10:50 amSan Juan Luis Munoz Marin Intl
May 20
SJU12:05 pmSan Juan Luis Munoz Marin Intl
3h 52m
HVN3:57 pmTweed-New Haven
$201

momondo Fare Finder

 
Customize your flight search to find flights from New Haven to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 3, 2026.
Use the filters below to find and compare flights from New Haven to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 4/22

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 4/29

12:05 pm-3:57 pm

Nonstop3h 52m

$157

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/9

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/13

12:05 pm-3:57 pm

Nonstop3h 52m

$188

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/9

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

$201

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 7/20

8:00 am-11:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Mon 7/27

1:03 pm-4:55 pm

Nonstop3h 52m

$205

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Wed 4/22

7:00 am-10:50 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 4/29

7:00 am-2:32 pm

1 stop7h 32m

$237

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 2/23

8:30 am-1:20 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:20 pm-5:25 pm

Nonstop4h 05m

$239

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/9

2:50 pm-10:09 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Wed 5/13

12:05 pm-3:57 pm

Nonstop3h 52m

$242

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 3/1

8:44 pm-10:09 am

1 stop12h 25m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:22 pm-11:27 am

1 stop20h 05m

$247

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

Mon 5/18

12:58 pm-4:50 pm

Nonstop3h 52m

$257

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 5/9

2:50 pm-10:09 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Wed 5/13

7:00 am-2:32 pm

1 stop7h 32m

$266

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from New Haven to Caribbean

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

What is the cheapest month to fly to Caribbean?

In general, October is the cheapest month to fly from New Haven to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $228. If you don’t want to visit Caribbean in October, then you should wait until November to fly from New Haven, when ticket prices are also cheap, with an average price of $229.

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

The cheapest day to depart from New Haven to Caribbean is on a Sunday when prices can be found for as low as $208. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $300. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

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

At noon is the cheapest time of day to fly from New Haven to Caribbean when you can find flight prices for as low as $232. Flying to Caribbean at noon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $284.

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

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

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

You are more likely to see cheaper flights to Caribbean from New Haven when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $303 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from New Haven for as low as $235 on momondo.

What cabin class options are available on Tweed-New Haven to Caribbean flights?

There is only 1 cabin class available to choose from on Tweed-New Haven to Caribbean flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap New Haven to Caribbean flight deals and tips

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

Best Price Found

$167

Fastest flight time

3h 50m

Direct flights

Tue, Thu, Sat and Sun

Airports in Caribbean

195 airports
The best one-way flight to Caribbean from New Haven in the past 72 hours is $167. The best round-trip flight deal from New Haven to Caribbean found on momondo in the last 72 hours is $193.
The fastest flight from New Haven to Caribbean takes 3h 50m
Direct flights go from New Haven to Caribbean on Tuesday, Thursday, Saturday and Sunday. The only airline offering direct flights is Avelo Airlines.
There are 195 airports in Caribbean. From New Haven there are direct flights to San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

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

    Prices for flights from Tweed-New Haven Airport to Caribbean refresh daily.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Tweed-New Haven Airport to Caribbean.

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

    The necessary travel and health documents for your Caribbean trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from New Haven to Caribbean?

Best airlines flying from New Haven to Caribbean

Compare and see reviews for airlines that fly from New Haven to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $101Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
Avelo AirlinesPriceFrom $179Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
JetBluePriceFrom $205Free CancellationRating
7.2
2,893 reviews
Search JetBlue flights

Why use momondo?

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

Finding the right flight to Caribbean 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 quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Caribbean from New Haven with this policy.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from New Haven to Caribbean.

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

Yes. momondo can track prices for New Haven to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo
Flights to San Juanfrom $65
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Flights to Nassaufrom $230
Flights to Saint Thomas Islandfrom $113
Flights to Santiago de los Caballerosfrom $201
Flights to Kingstonfrom $274
Flights to Simpson Bayfrom $170
Flights to Willemstadfrom $230
Flights to Port of Spainfrom $242