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Cheap flights from Connecticut to Caribbean Islands from $62

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Connecticut to Caribbean Islands departing on 3/4. 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 Connecticut to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
10:02 am - 6:58 pm
JFK
-
SJU
7h 56m
1 stop
Multiple Airlines Logo
8:50 am - 12:04 pm
SJU
-
JFK
4h 14mnonstop
$151Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Spirit Airlines Logo
9:55 am - 11:09 pm
LGA
-
SJU
12h 14m
1 stop
Spirit Airlines Logo
10:52 am - 7:00 pm
SJU
-
LGA
8h 08m
1 stop
$151Spirit Airlines
Sat, Mar 7 - Wed, Mar 11
Frontier Logo
12:00 pm - 3:57 pm
JFK
-
SJU
3h 57mnonstop
Frontier Logo
1:21 am - 5:30 am
SJU
-
JFK
4h 09mnonstop
$152Frontier
Mon, Apr 13 - Fri, Apr 17
Frontier Logo
1:00 pm - 5:58 pm
JFK
-
SJU
3h 58mnonstop
Frontier Logo
8:50 am - 12:04 pm
SJU
-
JFK
4h 14mnonstop
$153Frontier
Tue, Feb 24 - Wed, Mar 4
JetBlue Logo
1:15 pm - 5:11 pm
JFK
-
PUJ
3h 56mnonstop
JetBlue Logo
11:37 am - 11:08 pm
PUJ
-
JFK
11h 31m
1 stop
$275JetBlue
Tue, Mar 17 - Wed, Mar 18
Arajet Logo
11:00 am - 4:26 pm
EWR
-
PUJ
4h 26mnonstop
Arajet Logo
7:15 pm - 11:35 pm
PUJ
-
EWR
4h 20mnonstop
$275Arajet
Sat, Feb 21 - Tue, Mar 17
JetBlue Logo
2:15 pm - 6:14 pm
JFK
-
PUJ
3h 59mnonstop
JetBlue Logo
4:53 pm - 3:56 am
PUJ
-
JFK
11h 03m
1 stop
$276JetBlue
Tue, Apr 14 - Wed, Apr 15
Arajet Logo
12:00 pm - 4:26 pm
EWR
-
PUJ
4h 26mnonstop
Arajet Logo
7:15 pm - 11:35 pm
PUJ
-
EWR
4h 20mnonstop
$282Arajet
Sun, Mar 22 - Thu, Mar 26
American Airlines Logo
6:59 am - 10:53 am
JFK
-
PUJ
3h 54mnonstop
American Airlines Logo
11:54 am - 4:04 pm
PUJ
-
JFK
4h 10mnonstop
$282American Airlines
Mon, Mar 23 - Tue, Mar 31
American Airlines Logo
7:00 am - 10:57 am
JFK
-
PUJ
3h 57mnonstop
American Airlines Logo
11:51 am - 3:59 pm
PUJ
-
JFK
4h 08mnonstop
$284American Airlines
Sat, Apr 25 - Wed, Apr 29

JetBlue flights from Connecticut to Caribbean Islands

Our best JetBlue deals on Connecticut to Caribbean Islands flight tickets
JetBlue
Feb 24
JFK9:44 amNew York John F Kennedy Intl
3h 58m
SJU2:42 pmSan Juan Luis Munoz Marin Intl
Mar 1
SJU11:59 pmSan Juan Luis Munoz Marin Intl
4h 00m
JFK2:59 amNew York John F Kennedy Intl
$196
JetBlue
Feb 8
JFK6:50 pmNew York John F Kennedy Intl
4h 00m
SJU11:50 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU5:01 amSan Juan Luis Munoz Marin Intl
4h 07m
JFK8:08 amNew York John F Kennedy Intl
$217
JetBlue
Mar 17
JFK1:15 pmNew York John F Kennedy Intl
3h 56m
PUJ5:11 pmPunta Cana
Mar 18
PUJ11:37 amPunta Cana
11h 31m
1 stop
JFK11:08 pmNew York John F Kennedy Intl
$275

Frontier flights from Connecticut to Caribbean Islands

Our best Frontier deals on Connecticut to Caribbean Islands flight tickets
Frontier
Apr 13
JFK12:00 pmNew York John F Kennedy Intl
3h 57m
SJU3:57 pmSan Juan Luis Munoz Marin Intl
Apr 17
SJU1:21 amSan Juan Luis Munoz Marin Intl
4h 09m
JFK5:30 amNew York John F Kennedy Intl
$152
Frontier
Feb 24
JFK1:00 pmNew York John F Kennedy Intl
3h 58m
SJU5:58 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU8:50 amSan Juan Luis Munoz Marin Intl
4h 14m
JFK12:04 pmNew York John F Kennedy Intl
$153
Frontier
Feb 22
JFK1:00 pmNew York John F Kennedy Intl
3h 58m
SJU5:58 pmSan Juan Luis Munoz Marin Intl
Feb 25
SJU4:06 pmSan Juan Luis Munoz Marin Intl
9h 57m
1 stop
JFK1:03 amNew York John F Kennedy Intl
$155

momondo Fare Finder

 
Customize your flight search to find flights from Connecticut 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 February 3, 2026.
Use the filters below to find and compare flights from Connecticut to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 2/24

10:02 am-6:58 pm

1 stop7h 56m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:50 am-12:04 pm

Nonstop4h 14m

$151

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 3/7

9:55 am-11:09 pm

1 stop12h 14m

San Juan Luis Munoz Marin Intl

Wed 3/11

10:52 am-7:00 pm

1 stop8h 08m

$151

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 4/13

12:00 pm-3:57 pm

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Fri 4/17

1:21 am-5:30 am

Nonstop4h 09m

$152

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 2/24

1:00 pm-5:58 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Wed 3/4

8:50 am-12:04 pm

Nonstop4h 14m

$153

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Tue 3/17

1:15 pm-5:11 pm

Nonstop3h 56m

Punta Cana

Wed 3/18

11:37 am-11:08 pm

1 stop11h 31m

$275

NewarkPunta Cana

EWR - PUJ

EWRPUJ

Newark

Sat 2/21

11:00 am-4:26 pm

Nonstop4h 26m

Punta Cana

Tue 3/17

7:15 pm-11:35 pm

Nonstop4h 20m

$275

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Tue 4/14

2:15 pm-6:14 pm

Nonstop3h 59m

Punta Cana

Wed 4/15

4:53 pm-3:56 am

1 stop11h 03m

$276

NewarkPunta Cana

EWR - PUJ

EWRPUJ

Newark

Sun 3/22

12:00 pm-4:26 pm

Nonstop4h 26m

Punta Cana

Thu 3/26

7:15 pm-11:35 pm

Nonstop4h 20m

$282

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Mon 3/23

6:59 am-10:53 am

Nonstop3h 54m

Punta Cana

Tue 3/31

11:54 am-4:04 pm

Nonstop4h 10m

$282

New YorkPunta Cana

JFK - PUJ

JFKPUJ

New York John F Kennedy Intl

Sat 4/25

7:00 am-10:57 am

Nonstop3h 57m

Punta Cana

Wed 4/29

11:51 am-3:59 pm

Nonstop4h 08m

$284

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 Connecticut 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 March is, on average, the cheapest month to fly to Caribbean Islands from Connecticut, with most prices found around $271. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Connecticut averaging around $281.

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

The cheapest day to depart from Connecticut 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 $326. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $376. 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 Connecticut to Caribbean Islands in the afternoon for as low as $313. 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 at noon because they tend to be around $416. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Connecticut to Caribbean Islands flight route?

Fly from Hartford Bradley Intl to San Juan Luis Munoz Marin Intl for the best Connecticut - Caribbean Islands flight prices

What cabin class options are available on Connecticut to Caribbean Islands flights?

There are 2 cabin classes available to choose from on Connecticut 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 Connecticut to Caribbean Islands flights?

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

Cheap Connecticut to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 07m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Connecticut to Caribbean Islands takes 3h 07m
Direct flights go from Connecticut to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Connecticut there are direct flights to Santo Domingo Las Americas (SDQ), Santiago de los Caballeros (STI).
Search flight deals

  • When did momondo last update prices for flights from Connecticut to Caribbean Islands?

    Prices for flights from Connecticut to Caribbean Islands refresh daily.

  • How many operators does momondo search for flights from Connecticut to Caribbean Islands?

  • How old do you have to be to fly from Connecticut to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Connecticut to Caribbean Islands.

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

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Connecticut to Caribbean Islands?

Best airlines flying from Connecticut to Caribbean Islands

Compare and see reviews for airlines that fly from Connecticut to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $93Free CancellationRating
6.3
8,399 reviews
Search Spirit Airlines flights
FrontierPriceFrom $101Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
United AirlinesPriceFrom $110Free CancellationRating
7.4
9,231 reviews
Search United Airlines flights
Avelo AirlinesPriceFrom $116Free CancellationRating
7.6
88 reviews
Search Avelo Airlines flights
DeltaPriceFrom $150Free CancellationRating
7.9
8,135 reviews
Search Delta flights
JetBluePriceFrom $191Free CancellationRating
7.2
2,892 reviews
Search JetBlue flights
SouthwestPriceFrom $262Free CancellationRating
8.0
4,272 reviews
Search Southwest flights
American AirlinesPriceFrom $263Free CancellationRating
7.2
11,212 reviews
Search American Airlines flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Connecticut to Caribbean Islands. Millions of users trust and use momondo every year so you are in good hands.

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

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Connecticut with this policy.

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

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 Connecticut to Caribbean Islands.

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

Price alerts on flights to Caribbean Islands from Connecticut are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Caribbean Islands trip

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