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$72+ Cheap flights from Connecticut to Caribbean

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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap flight deals from Connecticut to Caribbean

Keep the following information in mind while searching for Connecticut to Caribbean flight deals. Data was last updated November 13, 2025.

Round-trip from

$153
(Kiwi.com)

One-way from

$72
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$339

Good round-trip deal

$208 or less

Good one-way deal

$161 or less
From Connecticut to Caribbean
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One-way flight from Connecticut to Caribbean
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Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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Price to beat on a round-trip flight from Connecticut to Caribbean.
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Price to beat on a one-way flight from Connecticut to Caribbean.
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Find flight deals from Connecticut to Caribbean

Cheapest flights from Connecticut to Caribbean
Explore the most affordable flight options available from Connecticut to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/11. 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 12/101:29 pmJFK - SJU
Nonstop3h 54mFrontier
Mon 12/223:54 amSJU - JFK
1 stop21h 44mFrontier
Deal found 11/11$153
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Mon 11/246:15 amJFK - SJU
1 stop17h 57mFrontier
Thu 12/49:15 amSJU - JFK
Nonstop4h 15mFrontier
Deal found 11/12$154
This Priceline deal was found by Cheapflights users on 11/13. 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.
Mon 12/159:59 amLGA - SJU
1 stop8h 51mMultiple Airlines
Sat 12/206:05 amSJU - LGA
Nonstop4h 18mMultiple Airlines
Deal found 11/13$154
This Super.com deal was found by Cheapflights users on 11/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/81:29 pmJFK - SJU
Nonstop3h 54mFrontier
Tue 12/169:15 amSJU - JFK
Nonstop4h 15mFrontier
Deal found 11/11$155
This Kiwi.com deal was found by Cheapflights users on 11/11. 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.
Tue 12/92:02 pmEWR - SJU
1 stop9h 14mMultiple Airlines
Fri 12/127:10 amSJU - EWR
Nonstop4h 25mMultiple Airlines
Deal found 11/11$155
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Thu 12/41:29 pmJFK - SJU
Nonstop3h 54mMultiple Airlines
Wed 12/105:00 pmSJU - JFK
2 stops32h 59mMultiple Airlines
Deal found 11/12$156
This Cheapflightsfares deal was found by Cheapflights users on 11/12. 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.
Wed 12/311:30 amEWR - SJU
Nonstop3h 43mFrontier
Fri 12/127:10 amSJU - EWR
Nonstop4h 25mFrontier
Deal found 11/12$156
This Super.com deal was found by Cheapflights users on 11/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/171:00 pmJFK - SJU
Nonstop3h 54mFrontier
Wed 11/199:00 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 11/12$157
This Super.com deal was found by Cheapflights users on 11/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/1410:30 pmEWR - SJU
Nonstop4h 03mFrontier
Wed 11/196:17 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 11/11$157
This Frontier deal was found by Cheapflights users on 11/10. 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.
Mon 11/171:00 pmJFK - SJU
Nonstop3h 54mFrontier
Tue 11/257:11 amSJU - JFK
Nonstop3h 54mFrontier
Deal found 11/10$158
This Gotogate deal was found by Cheapflights users on 11/13. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1510:30 pmEWR - SJU
Nonstop4h 03mMultiple Airlines
Fri 11/2111:55 amSJU - EWR
1 stop13h 36mMultiple Airlines
Deal found 11/13$158
This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Tue 12/21:29 pmJFK - SJU
Nonstop3h 54mMultiple Airlines
Mon 12/84:10 amSJU - JFK
2 stops29h 51mMultiple Airlines
Deal found 11/13$159

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut 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, Cheapflights users made 2,558,603 searches. Data last updated November 13, 2025.
Use the filters below to find and compare flights from Connecticut to Caribbean that are best for you.

Fly from

Connecticut

Fly to

Caribbean

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 1/27

12:00 pm-4:52 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-10:07 am

Nonstop4h 07m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 1/25

8:00 am-12:55 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-5:24 am

Nonstop4h 19m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 1/27

10:39 am-8:57 pm

1 stop9h 18m

San Juan Luis Munoz Marin Intl

Wed 2/4

3:55 pm-11:55 pm

1 stop9h 00m

$185

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 1/21

6:56 pm-11:59 pm

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:05 pm-9:32 pm

Nonstop4h 27m

$196

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Tue 12/2

6:00 am-4:36 pm

1 stop9h 36m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:10 am-4:11 pm

1 stop9h 01m

$205

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Mon 12/8

6:00 am-1:17 pm

1 stop6h 17m

San Juan Luis Munoz Marin Intl

Wed 12/17

8:30 am-9:07 pm

2 stops13h 37m

$213

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Mon 2/9

9:15 am-10:22 pm

2 stops12h 07m

San Juan Luis Munoz Marin Intl

Thu 2/12

8:35 am-4:13 pm

1 stop8h 38m

$215

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 1/21

7:00 am-3:30 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 1/30

4:40 pm-7:59 pm

Nonstop4h 19m

$225

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 2/4

7:00 am-3:30 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:00 am-10:13 am

Nonstop4h 13m

$225

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Tue 1/20

2:55 pm-10:22 pm

1 stop6h 27m

San Juan Luis Munoz Marin Intl

Tue 1/27

7:45 am-7:23 pm

2 stops12h 38m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean 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

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

Currently, January is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $101). Flying from Connecticut to Caribbean 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 CB?

Find hourly flight availability from Connecticut to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 32% on flights from Connecticut to Caribbean by exploring options for tickets in the afternoon.

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

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Connecticut to Caribbean 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

Explore weekly flight availability from Connecticut to Caribbean. 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 November 13, 2025.

The most flights from USCT to 0CB are scheduled on a Monday (2 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Caribbean. 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?

    A quick flight from Connecticut to Caribbean can take about 3h 52m. Delta provides one of the quickest options available for as low as $176. The distance between Connecticut and Caribbean is about 1601 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $79. Users have also found prices from $88 and $88 on Delta and JetBlue, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Connecticut to Caribbean 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?

    Currently, January is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $101). Flying from Connecticut to Caribbean 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Connecticut to Caribbean

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

Discover the top 8 airlines that operate flights from Connecticut to Caribbean. 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$330FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$429FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$110Average$520FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$116Average$295FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$186Average$524FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$545FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$676FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$275Average$566FlexibilityNo cancel feeOn-time71%

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