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Caribbean Islands

$74+ 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 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Jan 22 — Jan 291
Thu 1/22
Thu 1/29
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 December 23, 2025.

This Frontier deal was found by Cheapflights users on 12/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3112:00 pmLGA - SJU
1 stop13h 50mFrontier
Sat 1/108:20 amSJU - LGA
Nonstop4h 18mFrontier
Deal found 12/22$187
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:59 amJFK - SJU
1 stop11h 28mFrontier
Sat 1/109:23 pmSJU - JFK
1 stop13h 37mFrontier
Deal found 12/21$192
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:59 amJFK - SJU
1 stop7h 00mFrontier
Tue 2/38:00 amSJU - JFK
1 stop8h 27mFrontier
Deal found 12/21$193
This JetBlue deal was found by Cheapflights users on 12/21. 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.
Wed 12/318:59 pmJFK - SJU
Nonstop4h 00mJetBlue
Tue 2/38:15 amSJU - JFK
Nonstop4h 03mJetBlue
Deal found 12/21$196
This JetBlue deal was found by Cheapflights users on 12/22. 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 12/295:54 pmEWR - SJU
Nonstop4h 05mJetBlue
Fri 1/164:40 pmSJU - EWR
Nonstop4h 19mJetBlue
Deal found 12/22$196
This Priceline deal was found by Cheapflights users on 12/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/318:59 pmJFK - SJU
Nonstop4h 00mMultiple Airlines
Wed 1/73:28 pmSJU - JFK
1 stop9h 39mMultiple Airlines
Deal found 12/22$198
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:55 pmEWR - SJU
Nonstop4h 00mSpirit Airlines
Thu 1/155:50 pmSJU - EWR
Nonstop4h 15mSpirit Airlines
Deal found 12/22$209
This JetBlue deal was found by Cheapflights users on 12/22. 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.
Wed 12/315:00 pmJFK - SJU
Nonstop4h 09mJetBlue
Wed 12/311:59 amSJU - JFK
Nonstop4h 02mJetBlue
Deal found 12/22$211
This Kiwi.com deal was found by Cheapflights users on 12/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/311:55 pmEWR - SJU
Nonstop4h 00mMultiple Airlines
Fri 1/97:10 amSJU - EWR
Nonstop4h 25mMultiple Airlines
Deal found 12/21$211
This Trip.com deal was found by Cheapflights users on 12/22. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/305:01 amJFK - SJU
Nonstop3h 54mMultiple Airlines
Tue 1/63:55 amSJU - JFK
1 stop7h 05mMultiple Airlines
Deal found 12/22$212
This Frontier deal was found by Cheapflights users on 12/21. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:59 amJFK - SJU
1 stop7h 00mFrontier
Wed 1/73:55 amSJU - JFK
1 stop7h 05mFrontier
Deal found 12/21$213
This Kiwi.com deal was found by Cheapflights users on 12/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/317:59 amJFK - SJU
1 stop7h 00mFrontier
Fri 1/97:10 amSJU - JFK
Nonstop4h 15mFrontier
Deal found 12/22$214

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 December 23, 2025.

Round-trip from

$150
(Priceline)

One-way from

$74
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$420
From Connecticut to Caribbean Islands
Search Deals
One-way flight from Connecticut to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($15 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 23, 2025.
Use the filters below to find and compare flights from Connecticut to Caribbean Islands that are best for you.

Fly from

Connecticut

Fly to

Caribbean Islands

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 3/2

10:55 pm-3:50 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:55 am-9:59 am

Nonstop4h 04m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 2/24

7:55 am-12:49 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:05 am-5:24 am

Nonstop4h 19m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 1/30

6:50 pm-11:50 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:15 am-11:18 am

Nonstop4h 03m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 2/3

9:29 pm-2:25 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Wed 2/11

7:15 pm-10:20 pm

Nonstop4h 05m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Fri 2/20

8:35 pm-1:35 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Sat 2/28

6:00 am-9:16 am

Nonstop4h 16m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 1/18

7:37 pm-12:36 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Wed 1/21

2:05 am-5:24 am

Nonstop4h 19m

$196

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 3/20

10:29 pm-2:27 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Thu 4/2

7:00 pm-11:03 pm

Nonstop4h 03m

$196

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 1/6

7:10 pm-12:16 am

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Tue 1/13

6:01 am-9:17 am

Nonstop4h 16m

$196

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 3/11

10:59 pm-2:55 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Mon 3/16

3:26 am-7:32 am

Nonstop4h 06m

$216

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 3/15

6:50 pm-10:51 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Thu 3/26

6:55 pm-11:02 pm

Nonstop4h 07m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/22

Showing 1-10 of 60 results
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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, January is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $105). Flying from Connecticut to Caribbean Islands in September is currently the most expensive (average of $163). 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 December 23, 2025.

One of the essential ways to save on airfare from Connecticut to Caribbean Islands is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 33% on airfare.

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 December 16, 2024.

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

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 December 23, 2025.

The most flights from USCT to zzEPX are scheduled on a Monday (4 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 on average).

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 3h 54m. Fly via JetBlue, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1611 mi. Generally, flights for this route are nonstop.

  • 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 $63 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $67 and JetBlue from $88 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, January is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $105). Flying from Connecticut to Caribbean Islands in September is currently the most expensive (average of $163). 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

Browse thousands of different options on Cheapflights for your next trip

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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 8 airlines flying from Connecticut to Caribbean Islands

Discover the top 8 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 December 23, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$303FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$342FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$110Average$529FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$116Average$300FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$513FlexibilityNo cancel feeOn-time62%
DeltaCheapest$214Average$581FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$622FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$263Average$592FlexibilityNo cancel feeOn-time71%

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