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$78+ 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
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 July 31, 2025.

Round-trip from

$148
(CheapOair)

One-way from

$78
(Delta)

Good round-trip deal

$197 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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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 July 31, 2025.

This Priceline deal was found by Cheapflights users on 7/29. 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 11/119:00 pmEWR - SJU
Nonstop4h 03mFrontier
Sun 11/164:51 pmSJU - EWR
Nonstop4h 13mFrontier
Deal found 7/29$147
This Delta deal was found by Cheapflights users on 7/31. 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 10/76:00 amEWR - SJU
1 stop7h 19mDelta
Sat 10/117:15 amSJU - EWR
1 stop10h 53mDelta
Deal found 7/31$155
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:00 amJFK - SJU
Nonstop3h 54mFrontier
Sun 10/129:30 pmSJU - JFK
Nonstop4h 03mFrontier
Deal found 7/28$159
This Booking.com deal was found by Cheapflights users on 7/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/66:30 pmLGA - SJU
1 stop16h 34mSpirit Airlines
Thu 9/1111:59 amSJU - LGA
1 stop11h 26mSpirit Airlines
Deal found 7/30$170
This Trip.com deal was found by Cheapflights users on 7/29. 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.
Tue 10/218:40 amJFK - SJU
Nonstop4h 00mJetBlue
Fri 10/243:03 amSJU - JFK
Nonstop3h 57mJetBlue
Deal found 7/29$175
This Trip.com deal was found by Cheapflights users on 7/30. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:15 amEWR - SJU
Nonstop3h 55mJetBlue
Fri 9/265:00 pmSJU - EWR
Nonstop4h 04mJetBlue
Deal found 7/30$175
This FlightHub deal was found by Cheapflights users on 7/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1110:00 pmEWR - SJU
Nonstop4h 03mMultiple Airlines
Thu 8/148:00 pmSJU - EWR
1 stop17h 04mMultiple Airlines
Deal found 7/28$185
This CheapOair deal was found by Cheapflights users on 7/29. 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.
Fri 8/85:00 pmLGA - SJU
1 stop7h 46mMultiple Airlines
Sat 8/1610:10 amSJU - LGA
1 stop12h 44mMultiple Airlines
Deal found 7/29$195
This SmartFares deal was found by Cheapflights users on 7/30. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:30 amLGA - SJU
1 stop7h 41mFrontier
Fri 9/193:39 amSJU - LGA
1 stop8h 22mFrontier
Deal found 7/30$213
This Delta deal was found by Cheapflights users on 7/29. 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.
Tue 10/2112:59 pmLGA - SJU
1 stop9h 00mDelta
Tue 11/47:15 amSJU - LGA
1 stop9h 28mDelta
Deal found 7/29$225
This Cheapflightsfares deal was found by Cheapflights users on 7/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/411:00 amEWR - SDQ
Nonstop4h 26mArajet
Mon 11/106:10 amSDQ - EWR
Nonstop4h 20mArajet
Deal found 7/28$258
This Booking.com deal was found by Cheapflights users on 7/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/166:10 amEWR - SDQ
1 stop9h 50mMultiple Airlines
Thu 10/166:18 amSDQ - EWR
Nonstop4h 12mMultiple Airlines
Deal found 7/29$262

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 July 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

Thu 9/18

10:00 pm-1:58 am

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Sun 9/21

4:51 pm-9:02 pm

Nonstop4h 11m

$148

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 10/7

6:00 am-1:19 pm

1 stop7h 19m

San Juan Luis Munoz Marin Intl

Tue 10/21

7:15 am-6:08 pm

1 stop10h 53m

$155

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Thu 10/9

6:00 am-9:54 am

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 10/12

9:30 pm-1:33 am

Nonstop4h 03m

$159

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 9/6

6:30 pm-11:04 am

1 stop16h 34m

San Juan Luis Munoz Marin Intl

Thu 9/11

11:59 am-11:25 pm

1 stop11h 26m

$170

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 10/21

8:40 am-12:40 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Fri 10/24

3:03 am-7:00 am

Nonstop3h 57m

$175

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 9/16

6:15 am-10:10 am

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

Fri 9/26

5:00 pm-9:04 pm

Nonstop4h 04m

$175

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 8/11

10:00 pm-2:03 am

Nonstop4h 03m

San Juan Luis Munoz Marin Intl

Thu 8/14

8:00 pm-1:04 pm

1 stop17h 04m

$185

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Fri 8/8

5:00 pm-12:46 am

1 stop7h 46m

San Juan Luis Munoz Marin Intl

Sat 8/16

10:10 am-10:54 pm

1 stop12h 44m

$195

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 9/13

6:30 am-2:11 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

Fri 9/19

3:39 am-12:01 pm

1 stop8h 22m

$213

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Tue 10/21

3:00 pm-9:59 pm

1 stop6h 59m

San Juan Luis Munoz Marin Intl

Sat 10/25

2:29 pm-9:45 pm

1 stop7h 16m

$225

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 31, 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.

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 July 31, 2025.
Read through reviews of airlines operating flights from Connecticut to Caribbean, such as Delta, KLM, and Copa 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
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
7,981 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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.
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
1,493 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
8,900 reviews
Delta
8.0
Very good
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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
7,981 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Entertainment

7.9

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 Delta. According to our data, you can fly for as low as $78. Users have also found prices from $79 and $85 on Frontier 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, 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.
Newark to Fort Lauderdale flights
Dallas/Fort Worth to LaGuardia flights
John F Kennedy Intl to Heathrow flights
Newark to Heathrow flights
John F Kennedy Intl to Los Angeles flights
Los Angeles to Haneda flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Los Angeles to Newark flights
Dallas/Fort Worth to O'Hare Intl flights
Los Angeles to Las Vegas flights
John F Kennedy Intl to Cancún flights
Newark to O'Hare Intl flights
Newark to Los Angeles flights
Newark to Cancún flights
LaGuardia to O'Hare Intl flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
John F Kennedy Intl to Miami flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to Las Vegas flights
San Francisco to John F Kennedy Intl flights
Newark to Orlando flights
John F Kennedy Intl to O'Hare Intl flights
O'Hare Intl to LaGuardia flights
John F Kennedy Intl to Seattle flights
John F Kennedy Intl to San Francisco flights
Newark to Miami flights
O'Hare Intl to John F Kennedy Intl flights
O'Hare Intl to Newark flights
Los Angeles to Honolulu flights
Newark to Luis Munoz Marin Intl flights
LaGuardia to Miami flights
Los Angeles to Seattle flights
John F Kennedy Intl to Charles de Gaulle flights
LaGuardia to Dallas/Fort Worth flights
Atlanta to John F Kennedy Intl flights
O'Hare Intl to Cancún flights
Newark to Seattle flights
Fort Lauderdale to Newark flights
O'Hare Intl to Dallas/Fort Worth flights
Los Angeles to O'Hare Intl flights
Dallas/Fort Worth to Los Angeles flights
John F Kennedy Intl to Gatwick flights
Newark to San Francisco flights
Los Angeles to Dallas/Fort Worth flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
Dallas/Fort Worth to Newark flights
John F Kennedy Intl to Fort Lauderdale 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$290FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$373FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$116Average$293FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$184Average$522FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$563FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$572FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$267Average$694FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$277Average$590FlexibilityNo cancel feeOn-time71%

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