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Cheap flights from New Haven to Caribbean Islands from $101

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 Islands departing on 2/19. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from New Haven to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Avelo Airlines Logo
1:55 pm - 6:53 pm
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$239Avelo Airlines
Mon, Feb 2 - Fri, Feb 6
Avelo Airlines Logo
1:55 pm - 6:53 pm
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$241Avelo Airlines
Mon, Jan 26 - Fri, Feb 6
Avelo Airlines Logo
6:30 am - 11:28 am
HVN
-
SJU
3h 58mnonstop
Avelo Airlines Logo
7:54 pm - 10:59 pm
SJU
-
HVN
4h 05mnonstop
$263Avelo Airlines
Sat, Jan 17 - Mon, Feb 9
Avelo Airlines Logo
8:59 pm - 12:49 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
2:40 am - 6:45 am
SJU
-
HVN
4h 05mnonstop
$265Avelo Airlines
Sun, Mar 8 - Thu, Mar 12
Multiple Airlines Logo
6:26 pm - 5:53 pm
HVN
-
SJU
22h 27m1 stop
Multiple Airlines Logo
4:12 pm - 1:41 pm
SJU
-
HVN
22h 29m1 stop
$266Multiple Airlines
Mon, Jan 5 - Sat, Jan 10
Multiple Airlines Logo
5:58 pm - 2:32 pm
HVN
-
SJU
43h 34m2 stops
Multiple Airlines Logo
8:00 am - 7:04 pm
SJU
-
HVN
12h 04m1 stop
$267Multiple Airlines
Thu, Jan 15 - Thu, Jan 22
Avelo Airlines Logo
8:59 pm - 1:49 am
HVN
-
SJU
3h 50mnonstop
Avelo Airlines Logo
12:30 pm - 3:35 pm
SJU
-
HVN
4h 05mnonstop
$269Avelo Airlines
Thu, Feb 19 - Sat, Mar 7
Multiple Airlines Logo
6:30 am - 11:28 am
HVN
-
SJU
3h 58mnonstop
Multiple Airlines Logo
6:00 am - 1:27 pm
SJU
-
HVN
8h 27m1 stop
$273Multiple Airlines
Sat, Jan 10 - Thu, Jan 15
Multiple Airlines Logo
7:30 am - 9:57 am
HVN
-
SJU
26h 27m1 stop
Multiple Airlines Logo
2:40 am - 6:45 am
SJU
-
HVN
4h 05mnonstop
$288Multiple Airlines
Mon, Mar 23 - Thu, Mar 26
Multiple Airlines Logo
12:07 pm - 11:44 pm
HVN
-
SJU
10h 37m2 stops
Multiple Airlines Logo
9:23 pm - 2:01 pm
SJU
-
HVN
17h 38m1 stop
$290Multiple Airlines
Fri, Jan 9 - Mon, Jan 12

Avelo Airlines flights from New Haven to Caribbean Islands

Our best Avelo Airlines deals on New Haven to Caribbean Islands flight tickets
Avelo Airlines
Feb 2
HVN1:55 pmTweed-New Haven
3h 58m
SJU6:53 pmSan Juan Luis Munoz Marin Intl
Feb 6
SJU7:54 pmSan Juan Luis Munoz Marin Intl
4h 05m
HVN10:59 pmTweed-New Haven
$239
Find similar
Avelo Airlines
Jan 26
HVN1:55 pmTweed-New Haven
3h 58m
SJU6:53 pmSan Juan Luis Munoz Marin Intl
Feb 6
SJU7:54 pmSan Juan Luis Munoz Marin Intl
4h 05m
HVN10:59 pmTweed-New Haven
$241
Find similar
Avelo Airlines
Jan 17
HVN6:30 amTweed-New Haven
3h 58m
SJU11:28 amSan Juan Luis Munoz Marin Intl
Feb 9
SJU7:54 pmSan Juan Luis Munoz Marin Intl
4h 05m
HVN10:59 pmTweed-New Haven
$263
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from New Haven to Caribbean Islands 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 December 18, 2025.
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

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 2/2

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:54 pm-10:59 pm

Nonstop4h 05m

$239

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 1/26

1:55 pm-6:53 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:54 pm-10:59 pm

Nonstop4h 05m

$241

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 1/17

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Mon 2/9

7:54 pm-10:59 pm

Nonstop4h 05m

$263

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sun 3/8

8:59 pm-12:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Thu 3/12

2:40 am-6:45 am

Nonstop4h 05m

$265

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 1/5

6:26 pm-5:53 pm

1 stop22h 27m

San Juan Luis Munoz Marin Intl

Sat 1/10

4:12 pm-1:41 pm

1 stop22h 29m

$266

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 1/15

5:58 pm-2:32 pm

2 stops43h 34m

San Juan Luis Munoz Marin Intl

Thu 1/22

8:00 am-7:04 pm

1 stop12h 04m

$267

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Thu 2/19

8:59 pm-1:49 am

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Sat 3/7

12:30 pm-3:35 pm

Nonstop4h 05m

$269

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Sat 1/10

6:30 am-11:28 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:00 am-1:27 pm

1 stop8h 27m

$273

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Mon 3/23

7:30 am-9:57 am

1 stop26h 27m

San Juan Luis Munoz Marin Intl

Thu 3/26

2:40 am-6:45 am

Nonstop4h 05m

$288

New HavenSan Juan

HVN - SJU

HVNSJU

Tweed-New Haven

Fri 1/9

12:07 pm-11:44 pm

2 stops10h 37m

San Juan Luis Munoz Marin Intl

Mon 1/12

9:23 pm-2:01 pm

1 stop17h 38m

$290

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

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

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from New Haven, with most prices found around $228. The month of November is another great option to travel to Caribbean Islands, with average flight prices from New Haven averaging around $229.

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 $261. If your travel schedule is flexible, try to avoid departing on a Monday because tickets tend to average around $310. 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 in the afternoon. momondo users have found flights departing from New Haven to Caribbean Islands in the afternoon for as low as $170. 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 $287. 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 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 $313 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 $237 on momondo.

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

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

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

Mon, Tue, Thu, Fri, 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 Monday, Tuesday, Thursday, Friday, 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

  • 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?

  • 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?

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
FrontierPriceFrom $98Free CancellationRating
5.8
3,081 reviews
Search Frontier flights
JetBluePriceFrom $186Free CancellationRating
7.2
2,897 reviews
Search JetBlue flights
Avelo AirlinesPriceFrom $197Free CancellationRating
7.5
85 reviews
Search Avelo Airlines 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.

An easier way to manage your Caribbean Islands trip

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