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$62+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Mar 14 — Mar 211
Sat 3/14
Sat 3/21
1 adult, Economy
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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 February 12, 2026.

This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:39 am
EWR
-
SJU
Nonstop4h 00m
Spirit Airlines
Fri 2/276:27 pm
SJU
-
EWR
1 stop14h 38m
Spirit Airlines
Deal found 2/10$152
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:30 am
EWR
-
SJU
Nonstop3h 55m
Frontier
Wed 3/44:06 pm
SJU
-
EWR
1 stop10h 02m
Frontier
Deal found 2/10$153
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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.
Tue 2/249:04 am
EWR
-
SJU
Nonstop4h 00m
Spirit Airlines
Tue 3/105:27 pm
SJU
-
EWR
1 stop14h 38m
Spirit Airlines
Deal found 2/12$154
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2511:30 am
EWR
-
SJU
Nonstop3h 55m
Frontier
Wed 3/47:10 am
SJU
-
EWR
Nonstop4h 20m
Frontier
Deal found 2/10$155
This Frontier deal was found by Cheapflights users on 2/8. 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.
Tue 3/31:00 pm
JFK
-
SJU
Nonstop3h 58m
Frontier
Thu 3/58:50 am
SJU
-
JFK
Nonstop4h 14m
Frontier
Deal found 2/8$156
This Frontier deal was found by Cheapflights users on 2/8. 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.
Tue 3/311:30 am
EWR
-
SJU
Nonstop3h 55m
Frontier
Thu 3/57:10 am
SJU
-
EWR
Nonstop4h 20m
Frontier
Deal found 2/8$156
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Sun 2/221:00 pm
JFK
-
SJU
Nonstop3h 58m
Frontier
Wed 2/254:06 pm
SJU
-
JFK
1 stop9h 57m
Frontier
Deal found 2/11$157
This Priceline deal was found by Cheapflights users on 2/9. 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 3/312:30 pm
LGA
-
SJU
1 stop11h 13m
Multiple Airlines
Wed 3/411:52 am
SJU
-
LGA
1 stop8h 08m
Multiple Airlines
Deal found 2/9$157
This Cheapflightsfares deal was found by Cheapflights users on 2/9. 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.
Mon 2/2311:30 am
EWR
-
SJU
Nonstop3h 55m
Frontier
Wed 2/254:06 pm
SJU
-
EWR
1 stop10h 02m
Frontier
Deal found 2/9$157
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/231:00 pm
JFK
-
SJU
Nonstop3h 58m
Frontier
Thu 4/233:18 pm
SJU
-
JFK
1 stop9h 41m
Frontier
Deal found 2/10$158
This Expedia deal was found by Cheapflights users on 2/11. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:36 pm
LGA
-
SJU
Nonstop4h 02m
Frontier
Sat 5/24:00 pm
SJU
-
LGA
Nonstop4h 07m
Frontier
Deal found 2/11$158
This Frontier deal was found by Cheapflights users on 2/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2311:30 am
EWR
-
SJU
Nonstop3h 55m
Frontier
Thu 2/264:11 pm
SJU
-
EWR
1 stop9h 57m
Frontier
Deal found 2/11$158

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 February 12, 2026.

Round-trip from

$152
(CheapOair)

One-way from

$62
(Cheapflightsfares)

Popular in

December

Cheapest in

March

Average price

$350

Good round-trip deal

$194 or less

Good one-way deal

$113 or less
From Connecticut to Caribbean
Search Deals
One-way flight from Connecticut to Caribbean
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($22 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 February 2026
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 February 12, 2026.
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

Sat 5/16

8:02 am-2:31 pm

1 stop6h 29m

San Juan Luis Munoz Marin Intl

Fri 5/29

2:15 am-3:07 pm

1 stop12h 52m

$224

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 4/12

9:46 am-1:45 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Fri 4/17

3:56 pm-1:15 am

1 stop9h 19m

$232

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 3/3

11:32 am-9:00 pm

1 stop8h 28m

San Juan Luis Munoz Marin Intl

Tue 3/3

2:05 am-5:24 am

Nonstop4h 19m

$236

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 2/22

6:59 pm-11:59 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 2/27

7:00 am-10:05 am

Nonstop4h 05m

$237

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 5/16

7:30 pm-11:33 pm

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Sat 5/30

7:00 am-11:10 am

Nonstop4h 10m

$237

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 4/28

8:05 am-12:12 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Tue 5/5

5:42 pm-9:59 pm

Nonstop4h 17m

$237

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 5/9

7:45 pm-11:50 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Tue 5/12

6:45 pm-10:55 pm

Nonstop4h 10m

$237

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Fri 4/10

7:45 pm-11:50 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Tue 4/14

1:00 am-5:10 am

Nonstop4h 10m

$237

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 5/9

6:00 am-8:34 pm

2 stops14h 34m

San Juan Luis Munoz Marin Intl

Wed 5/13

4:55 pm-11:30 pm

1 stop6h 35m

$246

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 3/24

8:05 am-12:07 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Tue 3/31

7:00 am-11:11 am

Nonstop4h 11m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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, March is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $109). 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 February 12, 2026.

Unlike in the morning, when flights are generally more expensive, you can save up to 8% on flights from Connecticut to Caribbean by exploring options for tickets in the evening.

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 February 7, 2026.

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.

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. Spirit Airlines provides one of the quickest options available for as low as $232. 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 $59. Users have also found prices from $86 and $88 on JetBlue and Spirit Airlines, 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, March is the cheapest month in which you can book a flight from Connecticut to Caribbean (average of $109). 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 February 12, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$93Average$335FlexibilityNo cancel feeOn-time65%
FrontierCheapest$101Average$309FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$110Average$511FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$116Average$289FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$150Average$487FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$194Average$506FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$262Average$629FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$263Average$553FlexibilityNo cancel feeOn-time71%

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