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$79+ 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 10/3. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
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 August 7, 2025.

Round-trip from

$148
(Cheapflightsfares)

One-way from

$79
(Cheapflightsfares)

Popular in

December

Cheapest in

January

Average price

$284

Good round-trip deal

$256 or less

Good one-way deal

$134 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. 1% potential increase in price ($5 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 August 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 August 7, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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.
Thu 10/3010:00 pmEWR - SJU
Nonstop4h 03mFrontier
Fri 11/74:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 8/7$148
This CheapOair deal was found by Cheapflights users on 8/6. 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.
Sun 9/2110:00 pmEWR - SJU
Nonstop3h 58mFrontier
Fri 9/264:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/6$150
This Priceline deal was found by Cheapflights users on 8/4. 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.
Thu 10/3010:00 pmEWR - SJU
Nonstop4h 03mFrontier
Sun 11/24:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 8/4$151
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 10/2112:05 pmEWR - SJU
1 stop9h 54mDelta
Sat 10/257:15 amSJU - EWR
1 stop10h 53mDelta
Deal found 8/5$155
This FlightHub deal was found by Cheapflights users on 8/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2410:00 pmEWR - SJU
Nonstop4h 02mFrontier
Thu 10/304:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 8/7$156
This American Airlines deal was found by Cheapflights users on 8/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/211:30 pmEWR - SJU
1 stop8h 40mAmerican Airlines
Tue 10/281:50 pmSJU - EWR
1 stop9h 05mAmerican Airlines
Deal found 8/7$157
This CheapOair deal was found by Cheapflights users on 8/6. 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.
Fri 9/2610:00 pmEWR - SJU
Nonstop3h 58mFrontier
Sat 10/114:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 8/6$158
This Frontier deal was found by Cheapflights users on 8/7. 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 10/1310:00 pmEWR - SJU
Nonstop4h 02mFrontier
Sat 10/184:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 8/7$160
This CheapOair deal was found by Cheapflights users on 8/6. 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 10/16:00 amJFK - SJU
Nonstop3h 56mFrontier
Mon 10/136:22 amSJU - JFK
Nonstop4h 03mFrontier
Deal found 8/6$161
This SmartFares deal was found by Cheapflights users on 8/7. 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.
Thu 9/1810:00 pmEWR - SJU
Nonstop3h 58mFrontier
Mon 9/294:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/7$161
This Frontier deal was found by Cheapflights users on 8/5. 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.
Fri 9/266:00 amJFK - SJU
Nonstop3h 56mFrontier
Wed 10/19:26 pmSJU - JFK
Nonstop3h 59mFrontier
Deal found 8/5$162
This Cheapflightsfares deal was found by Cheapflights users on 8/7. 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.
Fri 9/1910:00 pmEWR - SJU
Nonstop3h 58mFrontier
Tue 9/234:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/7$162

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 August 7, 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

Thu 10/30

10:00 pm-2:03 am

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Fri 11/7

4:51 pm-8:04 pm

Nonstop4h 13m

$148

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 9/21

10:00 pm-1:58 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 9/26

4:51 pm-9:02 pm

Nonstop4h 11m

$150

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Thu 10/30

10:00 pm-2:03 am

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Sun 11/2

4:51 pm-8:04 pm

Nonstop4h 13m

$151

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 10/21

12:05 pm-9:59 pm

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Sat 10/25

7:15 am-6:08 pm

1 stop10h 53m

$155

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Fri 10/24

10:00 pm-2:02 am

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Thu 10/30

4:51 pm-9:04 pm

Nonstop4h 13m

$156

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 10/21

1:30 pm-10:10 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:50 pm-10:55 pm

1 stop9h 05m

$157

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Fri 9/26

10:00 pm-1:58 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sat 10/11

4:51 pm-9:04 pm

Nonstop4h 13m

$158

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 10/13

10:00 pm-2:02 am

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Sat 10/18

4:51 pm-9:04 pm

Nonstop4h 13m

$160

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 10/1

6:00 am-9:56 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Mon 10/13

6:22 am-10:25 am

Nonstop4h 03m

$161

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Thu 9/18

10:00 pm-1:58 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Mon 9/29

4:51 pm-9:02 pm

Nonstop4h 11m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/4

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 August 7, 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 August 7, 2025.

The most flights from USCT to 0CB are scheduled on a Wednesday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 7, 2025.
Read through reviews of airlines operating flights from Connecticut to Caribbean, such as Delta, Copa Airlines, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Delta
8.0
Very good
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
Copa Airlines
7.5
Good
1,500 reviews
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.
JetBlue
7.2
Good
2,915 reviews
Delta
8.0
Very good
7,987 reviews

Comfort

7.9

Overall

8.0

Crew

8.5

Entertainment

7.9

Boarding

8.2

Food

7.3

Reviews

1 / 20
10.0
Excellent

Kymberlee,Oct 2024

JFK - ATL

Overall it was good on the flight. Before the flight with checking the bag at JFK was a nightmare. It took way too long and the Delta concierge was very rude to everyone. But other than that it was fine.

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.

  • 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 $79. Users have also found prices from $88 and $90 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, 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

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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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$312FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$376FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$116Average$294FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$186Average$524FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$555FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$262Average$692FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$277Average$591FlexibilityNo cancel feeOn-time71%

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