HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Jan 30 — Feb 61
Fri 1/30
Fri 2/6
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Connecticut to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 December 31, 2025.

This Priceline deal was found by Cheapflights users on 12/30. 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
Thu 1/157:15 amSJU - JFK
Nonstop4h 14mMultiple Airlines
Deal found 12/30$266
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 12/314:43 pmEWR - SJU
2 stops32h 51mMultiple Airlines
Sat 1/315:50 pmSJU - EWR
Nonstop4h 15mMultiple Airlines
Deal found 12/30$267
This Kiwi.com deal was found by Cheapflights users on 12/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3110:30 pmEWR - SJU
2 stops19h 43mMultiple Airlines
Sat 1/106:08 pmSJU - EWR
Nonstop4h 25mMultiple Airlines
Deal found 12/29$274
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/311:55 pmEWR - SJU
Nonstop4h 00mSpirit Airlines
Wed 1/74:55 pmSJU - EWR
1 stop8h 34mSpirit Airlines
Deal found 12/29$276
This Expedia deal was found by Cheapflights users on 12/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/315:54 pmEWR - SJU
Nonstop4h 05mMultiple Airlines
Fri 1/97:10 amSJU - EWR
Nonstop4h 25mMultiple Airlines
Deal found 12/29$280
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:37 pmEWR - SJU
Nonstop3h 59mUnited Airlines
Fri 1/302:05 amSJU - EWR
Nonstop4h 19mUnited Airlines
Deal found 12/30$281
This Priceline deal was found by Cheapflights users on 12/30. 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 12/315:51 amEWR - SJU
1 stop15h 14mSpirit Airlines
Sat 1/315:50 pmSJU - EWR
Nonstop4h 15mSpirit Airlines
Deal found 12/30$283
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:54 pmJFK - SJU
Nonstop4h 05mDelta
Tue 2/37:00 amSJU - JFK
Nonstop4h 07mDelta
Deal found 12/29$285
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/317:37 pmEWR - SJU
Nonstop3h 59mUnited Airlines
Thu 1/158:35 amSJU - EWR
1 stop8h 41mUnited Airlines
Deal found 12/30$286
This United Airlines deal was found by Cheapflights users on 12/30. 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 12/312:20 pmLGA - SJU
2 stops14h 51mUnited Airlines
Thu 1/158:35 amSJU - LGA
1 stop8h 38mUnited Airlines
Deal found 12/30$295
This Priceline deal was found by Cheapflights users on 12/29. 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.
Wed 12/317:10 pmBDL - SJU
Nonstop3h 49mMultiple Airlines
Wed 1/1412:59 pmSJU - BDL
Nonstop4h 15mMultiple Airlines
Deal found 12/29$298
This CheapOair deal was found by Cheapflights users on 12/29. 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.
Wed 12/3111:30 amEWR - SJU
Nonstop3h 43mFrontier
Thu 1/84:39 pmSJU - EWR
1 stop9h 31mFrontier
Deal found 12/29$300

Find flight deals from Connecticut to Caribbean

Keep the following information in mind while searching for Connecticut to Caribbean flight deals. Data was last updated December 31, 2025.

Round-trip from

$142
(Cheapflightsfares)

One-way from

$74
(Super.com)

Popular in

December

Cheapest in

January

Average price

$411

Good round-trip deal

$257 or less

Good one-way deal

$97 or less
From Connecticut to Caribbean
Search Deals
One-way flight from Connecticut to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($13 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
Price to beat on a round-trip flight from Connecticut to Caribbean.
Search Deals
Price to beat on a one-way flight from Connecticut to Caribbean.
Search Deals

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 December 31, 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

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 1/26

7:10 pm-12:16 am

Nonstop4h 06m

San Juan Luis Munoz Marin Intl

Fri 1/30

6:01 am-9:17 am

Nonstop4h 16m

$168

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 1/31

7:37 pm-12:36 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Mon 2/2

2:05 am-5:24 am

Nonstop4h 19m

$168

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 1/31

7:37 pm-12:36 am

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Tue 2/10

2:05 am-5:24 am

Nonstop4h 19m

$168

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Thu 2/19

8:35 pm-1:35 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:00 am-9:16 am

Nonstop4h 16m

$172

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 2/22

8:35 pm-1:35 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:00 am-9:16 am

Nonstop4h 16m

$172

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 2/24

6:00 am-3:40 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:05 am-5:24 am

Nonstop4h 19m

$173

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 2/1

9:59 am-2:56 pm

Nonstop3h 57m

San Juan Luis Munoz Marin Intl

Sun 2/8

7:15 pm-10:20 pm

Nonstop4h 05m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 1/31

6:50 pm-11:50 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Tue 2/3

7:15 pm-10:20 pm

Nonstop4h 05m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 1/30

9:29 pm-2:25 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Wed 2/4

9:25 am-12:30 pm

Nonstop4h 05m

$176

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 2/1

9:29 pm-2:25 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Wed 2/4

11:06 am-2:12 pm

Nonstop4h 06m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/29

Showing 1-10 of 60 results
1
2
3
...
6

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 $102). 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 December 31, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 13% 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 27, 2025.

Travelers seeking maximum savings on their Connecticut to Caribbean flight should consider departing on Wednesday at noon when fares are most often at their lowest. Thursday 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 December 31, 2025.

The most flights from USCT to 0CB are scheduled on a Monday (4 on average). You will have fewer flight options on Thursday, 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 59m. JetBlue provides one of the quickest options available for as low as $168. The distance between Connecticut and Caribbean is about 1611 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 Frontier. According to our data, you can fly for as low as $64. Users have also found prices from $67 and $88 on Spirit Airlines 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 $102). 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.
John F Kennedy Intl to Fort Lauderdale flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Miami flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to West Palm Beach flights
Newark to Cancún flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Las Vegas flights
Los Angeles to Haneda flights
O'Hare Intl to Cancún flights
John F Kennedy Intl to Los Angeles flights
Newark to Las Vegas flights
Dallas/Fort Worth to LaGuardia flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Mexico City flights
Newark to Orlando flights
John F Kennedy Intl to Orlando flights
Newark to Mexico City flights
O'Hare Intl to Las Vegas flights
Los Angeles to John F Kennedy Intl flights
Dallas/Fort Worth to John F Kennedy Intl flights
LaGuardia to Orlando flights
Baltimore to Fort Lauderdale flights
Dallas/Fort Worth to Las Vegas flights
Boston to Fort Lauderdale flights
Minneapolis to Sky Harbor Intl flights
John F Kennedy Intl to Heathrow flights
Dulles Intl to Cancún flights
Boston to Miami flights
Reagan-National to Miami flights
LaGuardia to Cancún flights
Seattle to Los Angeles flights
Newark to Heathrow flights
Newark to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Cancún flights
John F Kennedy Intl to Haneda flights
LaGuardia to Tampa flights
Dulles Intl to Miami flights
Detroit to Fort Lauderdale flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to Charles de Gaulle flights
John F Kennedy Intl to Dallas/Fort Worth flights
San Francisco to John F Kennedy Intl flights
Seattle to Las Vegas flights
Los Angeles to Seattle flights
O'Hare Intl to Sky Harbor Intl flights
Los Angeles to Honolulu flights

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 December 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$98Average$304FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$340FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$110Average$527FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$116Average$300FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$510FlexibilityNo cancel feeOn-time62%
DeltaCheapest$214Average$555FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$262Average$617FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$263Average$592FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.