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Caribbean Islands

$117+ Cheap flights from Connecticut to Caribbean Islands

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 7/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Jul 6 — Jul 131
Mon 7/6
Mon 7/13
1 adult, Economy
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Cheap flight deals from Connecticut to Caribbean Islands

Cheapest flights from Connecticut to Caribbean Islands
Explore the most affordable flight options available from Connecticut to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 6, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 6/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:25 pm
EWR
-
SJU
Nonstop4h 03m
JetBlue
Tue 7/77:48 pm
SJU
-
EWR
Nonstop4h 03m
JetBlue
Deal found 6/1$252
This lol.travel deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/139:55 pm
EWR
-
SJU
Nonstop4h 04m
JetBlue
Wed 7/226:00 am
SJU
-
EWR
Nonstop3h 59m
JetBlue
Deal found 6/2$254
This United Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:47 pm
EWR
-
SJU
Nonstop4h 03m
United Airlines
Tue 9/11:00 am
SJU
-
EWR
Nonstop4h 04m
United Airlines
Deal found 6/3$257
This Cheapflightsfares deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:25 pm
EWR
-
SJU
Nonstop4h 03m
JetBlue
Thu 7/99:30 pm
SJU
-
EWR
Nonstop4h 02m
JetBlue
Deal found 6/5$262
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/209:55 pm
EWR
-
SJU
Nonstop4h 04m
JetBlue
Thu 7/239:30 pm
SJU
-
EWR
Nonstop4h 02m
JetBlue
Deal found 6/5$267
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/410:25 pm
EWR
-
SJU
Nonstop4h 03m
JetBlue
Fri 7/106:00 am
SJU
-
EWR
Nonstop3h 59m
JetBlue
Deal found 6/5$269
This American Airlines deal was found by Cheapflights users on 6/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:32 pm
JFK
-
SJU
1 stop15h 11m
American Airlines
Wed 8/263:47 pm
SJU
-
JFK
1 stop7h 13m
American Airlines
Deal found 6/3$271
This American Airlines deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/199:20 am
LGA
-
SJU
1 stop6h 43m
American Airlines
Tue 8/254:53 pm
SJU
-
LGA
1 stop6h 50m
American Airlines
Deal found 6/2$271
This SmartFares deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/218:29 am
JFK
-
SJU
Nonstop3h 56m
JetBlue
Wed 8/269:10 pm
SJU
-
JFK
Nonstop3h 57m
JetBlue
Deal found 6/4$272
This lol.travel deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure lol.travel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/158:00 pm
JFK
-
SJU
Nonstop4h 13m
JetBlue
Wed 6/245:01 am
SJU
-
JFK
Nonstop3h 53m
JetBlue
Deal found 6/2$273
This Flysmarter deal was found by Cheapflights users on 6/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/208:00 pm
JFK
-
SJU
Nonstop4h 13m
JetBlue
Wed 7/298:10 pm
SJU
-
JFK
Nonstop3h 57m
JetBlue
Deal found 6/2$274
This American Airlines deal was found by Cheapflights users on 6/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:00 pm
JFK
-
SJU
1 stop6h 59m
American Airlines
Wed 8/197:30 am
SJU
-
JFK
1 stop6h 27m
American Airlines
Deal found 6/4$276

Find flight deals from Connecticut to Caribbean Islands

Keep the following information in mind while searching for Connecticut to Caribbean Islands flight deals. Data was last updated June 6, 2026.

Round-trip from

$252
(Cheapflightsfares)

One-way from

$117
(SmartFares)

Popular in

December

Cheapest in

January

Average price

$362
From Connecticut to Caribbean Islands
Search Deals
One-way flight from Connecticut to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($2 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
Search Deals

Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated June 6, 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

Cheapest round-trip

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 8/7

7:28 pm-11:52 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Fri 8/14

1:19 pm-5:30 pm

Nonstop4h 11m

$322

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 7/20

9:00 pm-7:57 am

1 stop10h 57m

San Juan Luis Munoz Marin Intl

Wed 7/29

8:10 pm-12:07 am

Nonstop3h 57m

$327

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Thu 9/3

6:00 am-12:54 pm

1 stop6h 54m

San Juan Luis Munoz Marin Intl

Wed 9/9

3:56 pm-12:57 am

1 stop9h 01m

$336

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 8/17

6:00 pm-10:08 pm

Nonstop4h 08m

San Juan Luis Munoz Marin Intl

Thu 8/20

2:20 am-8:46 am

1 stop6h 26m

$346

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 8/19

7:28 pm-11:52 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Sun 8/23

7:30 am-11:25 am

Nonstop3h 55m

$347
Quickest round-trip

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 8/17

6:00 am-9:58 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Wed 8/19

6:00 am-9:59 am

Nonstop3h 59m

$347

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Thu 8/27

12:00 pm-3:58 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sat 9/5

2:20 am-8:46 am

1 stop6h 26m

$356

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Wed 8/12

7:15 am-6:10 pm

2 stops10h 55m

San Juan Luis Munoz Marin Intl

Wed 8/26

11:50 am-11:00 pm

2 stops11h 10m

$360

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 6/21

7:25 pm-11:43 pm

Nonstop4h 18m

San Juan Luis Munoz Marin Intl

Sat 6/27

7:05 am-11:01 am

Nonstop3h 56m

$362

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 7/31

7:29 pm-11:53 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Sat 8/15

5:50 pm-10:04 pm

Nonstop4h 14m

$362

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/1

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Connecticut to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Connecticut with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Connecticut to Caribbean Islands

What is the cheapest month to book a flight from Connecticut to Caribbean Islands?

Currently, October is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $120). Flying from Connecticut to Caribbean Islands in December is currently the most expensive (average of $780). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from CT to EPX?

Find hourly flight availability from Connecticut to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 6, 2026.

One of the essential ways to save on airfare from Connecticut to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 26% on airfare.

Weekly flight availability from Connecticut to Caribbean Islands

Explore weekly flight availability from Connecticut to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated June 6, 2026.

The most flights from USCT to zzEPX are scheduled on a Monday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (2 on average).

How far ahead should I book a flight from Connecticut to Caribbean Islands?

The price you pay for your flight from Connecticut to Caribbean Islands may vary depending on when you book. For the best chance of a lower fare, look to book 69 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest day to fly from Connecticut to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Caribbean Islands. Price data was last updated on May 30, 2026.

Travelers seeking maximum savings on their Connecticut to Caribbean Islands flight should consider departing on Wednesday at noon when fares are most often at their lowest. Wednesday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Caribbean Islands?

    There are many flights that can get you from Connecticut to Caribbean Islands in 4h 24m. Fly via Delta, JetBlue, or United Airlines to get the fastest option. Airlines will cover a distance of 1601 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Connecticut to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as $66 on Frontier. Other airlines that offer cheap prices include JetBlue from $88 and Avelo Airlines from $98 one-way.

  • Can I find deals for flights from Connecticut to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Connecticut to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Caribbean Islands.

  • Can I find deals for business class flights from Connecticut to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Connecticut to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Connecticut to Caribbean Islands?

    Currently, October is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $120). Flying from Connecticut to Caribbean Islands in December is currently the most expensive (average of $780). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Connecticut to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Connecticut to Caribbean Islands

Discover the top 7 airlines that operate flights from Connecticut to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated June 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$89Average$335FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$110Average$453FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$112Average$338FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$152Average$467FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$208Average$502FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$262Average$610FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$263Average$587FlexibilityNo cancel feeOn-time71%

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