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$74+ 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 1/13. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Oct 29 — Nov 51
Wed 10/29
Wed 11/5
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 September 29, 2025.

Round-trip from

$127
(Trip.com)

One-way from

$74
(Trip.com)

Popular in

December

Cheapest in

January

Average price

$319

Good round-trip deal

$186 or less

Good one-way deal

$113 or less
From Connecticut to Caribbean
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One-way flight from Connecticut to Caribbean
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High demand for flights, 2% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 29, 2025.

This Trip.com deal was found by Cheapflights users on 9/27. 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.
Sat 10/188:40 pmJFK - SJU
Nonstop4h 07mJetBlue
Fri 10/249:25 pmSJU - JFK
Nonstop3h 51mJetBlue
Deal found 9/27$127
This CheapOair deal was found by Cheapflights users on 9/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/111:00 pmJFK - SJU
Nonstop3h 54mFrontier
Wed 11/199:00 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 9/29$128
This Kiwi.com deal was found by Cheapflights users on 9/26. 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.
Sun 11/21:00 pmJFK - SJU
Nonstop3h 54mFrontier
Tue 11/49:00 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 9/26$129
This Kiwi.com deal was found by Cheapflights users on 9/26. 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.
Sat 11/12:00 pmJFK - SJU
Nonstop3h 54mFrontier
Tue 11/49:00 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 9/26$130
This Trip.com deal was found by Cheapflights users on 9/28. 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.
Wed 10/1511:30 amJFK - SJU
Nonstop3h 54mFrontier
Sun 10/196:22 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 9/28$131
This Trip.com deal was found by Cheapflights users on 9/28. 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.
Fri 11/1410:59 pmJFK - SJU
Nonstop3h 49mJetBlue
Fri 11/218:20 pmSJU - JFK
Nonstop4h 03mJetBlue
Deal found 9/28$132
This Trip.com deal was found by Cheapflights users on 9/29. 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.
Sat 10/188:40 pmJFK - SJU
Nonstop4h 07mJetBlue
Sat 10/256:00 pmSJU - JFK
Nonstop3h 58mJetBlue
Deal found 9/29$133
This Cheapflightsfares deal was found by Cheapflights users on 9/27. 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 10/410:00 pmEWR - SJU
Nonstop3h 58mFrontier
Sat 10/114:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 9/27$135
This Priceline deal was found by Cheapflights users on 9/29. 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.
Tue 10/287:18 pmEWR - SJU
1 stop6h 26mMultiple Airlines
Sat 11/15:51 pmSJU - EWR
Nonstop4h 13mMultiple Airlines
Deal found 9/29$136
This Trip.com deal was found by Cheapflights users on 9/29. 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.
Mon 10/2710:59 pmJFK - SJU
Nonstop3h 49mJetBlue
Mon 11/36:27 amSJU - JFK
Nonstop4h 02mJetBlue
Deal found 9/29$137
This SmartFares deal was found by Cheapflights users on 9/28. 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.
Wed 12/317:35 pmEWR - SJU
Nonstop4h 06mJetBlue
Sat 1/177:00 amSJU - EWR
Nonstop4h 13mJetBlue
Deal found 9/28$139
This Cheapflightsfares deal was found by Cheapflights users on 9/26. 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 10/2211:30 amJFK - SJU
Nonstop3h 54mFrontier
Tue 10/289:00 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 9/26$143

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 September 29, 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

Mon 11/17

12:30 pm-5:20 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Fri 11/21

7:15 am-10:25 am

Nonstop4h 10m

$152

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 10/24

5:25 pm-9:24 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Sun 11/2

5:27 am-8:29 am

Nonstop4h 02m

$152

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 11/8

7:37 pm-12:36 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Mon 11/10

2:05 am-5:24 am

Nonstop4h 19m

$152

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 11/17

8:00 am-12:56 pm

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Wed 11/19

6:35 pm-9:52 pm

Nonstop4h 17m

$152

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 11/14

10:59 pm-3:48 am

Nonstop3h 49m

San Juan Luis Munoz Marin Intl

Fri 11/21

8:20 pm-11:23 pm

Nonstop4h 03m

$152

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 2/4

8:05 am-1:07 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 2/11

7:00 am-10:14 am

Nonstop4h 14m

$152

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 1/12

7:10 pm-12:16 am

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Fri 1/23

7:00 am-10:13 am

Nonstop4h 13m

$152

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 2/2

8:00 am-12:55 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:50 pm-11:59 pm

1 stop7h 09m

$157

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 10/27

6:00 am-12:17 pm

1 stop6h 17m

San Juan Luis Munoz Marin Intl

Sun 11/2

2:05 am-5:24 am

Nonstop4h 19m

$157

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 1/28

8:35 am-8:30 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Wed 2/4

7:00 am-10:14 am

Nonstop4h 14m

$157

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

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, September is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $254). Flying from Connecticut to Caribbean in June is currently the most expensive (average of $339). 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 September 29, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Connecticut to Caribbean as you normally would.

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 September 29, 2025.

The most flights from USCT to 0CB are scheduled on a Monday (2 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 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 50m. Delta provides one of the quickest options available for as low as $152. The distance between Connecticut and Caribbean is about 1601 mi. Most flights are nonstop.

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

    For one-way options, check prices for JetBlue. According to our data, you can fly for as low as $76. Users have also found prices from $76 and $81 on United Airlines and Delta, 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, September is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $254). Flying from Connecticut to Caribbean in June is currently the most expensive (average of $339). 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 September 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$80Average$327FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$390FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$110Average$532FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$116Average$294FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$170Average$511FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$563FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$698FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$277Average$599FlexibilityNo cancel feeOn-time71%

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