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$76+ 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 5/18. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
May 5 — May 121
Mon 5/5
Mon 5/12
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 April 30, 2025.

Round-trip from

$137
(Kiwi.com)

One-way from

$76
(eDestinos)

Good round-trip deal

$240 or less

Good one-way deal

$103 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 April 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/29. 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.
Mon 5/2610:01 pmEWR - SJU
Nonstop4h 00mMultiple Airlines
Thu 5/298:12 pmSJU - EWR
1 stop12h 55mMultiple Airlines
Deal found 4/29$137
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/285:15 amEWR - SJU
1 stop9h 45mSpirit Airlines
Thu 5/298:12 pmSJU - EWR
1 stop12h 55mSpirit Airlines
Deal found 4/29$143
This eDestinos deal was found by Cheapflights users on 4/28. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1911:24 amEWR - SJU
Nonstop4h 00mFrontier
Thu 5/224:53 pmSJU - EWR
Nonstop4h 07mFrontier
Deal found 4/28$163
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Wed 5/2111:29 amJFK - SJU
Nonstop4h 00mFrontier
Thu 5/296:20 amSJU - JFK
Nonstop4h 05mFrontier
Deal found 4/28$166
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1310:00 pmJFK - SJU
Nonstop4h 21mJetBlue
Mon 6/168:30 pmSJU - JFK
Nonstop3h 56mJetBlue
Deal found 4/28$196
This JetBlue deal was found by Cheapflights users on 4/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/209:45 pmEWR - SJU
Nonstop4h 01mJetBlue
Sat 5/2410:40 pmSJU - EWR
Nonstop4h 06mJetBlue
Deal found 4/28$196
This Delta deal was found by Cheapflights users on 4/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1612:45 pmJFK - SJU
Nonstop3h 59mDelta
Wed 5/211:12 pmSJU - JFK
Nonstop4h 18mDelta
Deal found 4/27$201
This Cheapflightsfares deal was found by Cheapflights users on 4/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/286:00 amLGA - SJU
1 stop9h 00mSpirit Airlines
Tue 6/31:33 amSJU - LGA
1 stop13h 27mSpirit Airlines
Deal found 4/29$201
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:55 amEWR - SJU
Nonstop4h 02mUnited Airlines
Wed 5/211:05 amSJU - EWR
Nonstop4h 09mUnited Airlines
Deal found 4/28$201
This American Airlines deal was found by Cheapflights users on 4/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/611:30 amJFK - SJU
1 stop9h 03mAmerican Airlines
Wed 5/76:10 amSJU - JFK
1 stop11h 19mAmerican Airlines
Deal found 4/28$210
This United Airlines deal was found by Cheapflights users on 4/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/286:00 amLGA - SJU
1 stop8h 38mUnited Airlines
Tue 10/284:50 pmSJU - LGA
1 stop6h 32mUnited Airlines
Deal found 4/28$210
This American Airlines deal was found by Cheapflights users on 4/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:21 amLGA - SJU
1 stop8h 39mAmerican Airlines
Sun 5/116:30 amSJU - LGA
1 stop9h 34mAmerican Airlines
Deal found 4/29$225

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 April 30, 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 5/26

10:01 pm-2:01 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-9:07 am

1 stop12h 55m

$137

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 5/28

5:15 am-3:00 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-9:07 am

1 stop12h 55m

$143

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Mon 5/19

11:24 am-3:24 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/22

4:53 pm-9:00 pm

Nonstop4h 07m

$163

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 5/21

11:29 am-3:29 pm

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Thu 5/29

6:20 am-10:25 am

Nonstop4h 05m

$166

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 6/13

7:30 pm-11:54 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Fri 6/20

7:00 am-11:07 am

Nonstop4h 07m

$196

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 5/20

9:45 pm-1:46 am

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sat 5/24

10:40 pm-2:46 am

Nonstop4h 06m

$196

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 5/14

7:55 am-11:57 am

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Wed 5/21

1:05 am-5:14 am

Nonstop4h 09m

$201

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Wed 5/28

6:00 am-3:00 pm

1 stop9h 00m

San Juan Luis Munoz Marin Intl

Tue 6/3

1:33 am-3:00 pm

1 stop13h 27m

$201

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 6/14

7:29 pm-11:50 pm

Nonstop4h 21m

San Juan Luis Munoz Marin Intl

Tue 6/17

3:23 am-7:24 am

Nonstop4h 01m

$206

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 5/6

11:30 am-8:33 pm

1 stop9h 03m

San Juan Luis Munoz Marin Intl

Wed 5/7

6:10 am-5:29 pm

1 stop11h 19m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

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 December is currently the most expensive (average of $336). 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 April 30, 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.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 30, 2025.
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Japan Airlines
8.3
Very good
1,459 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Delta
8.0
Very good
7,936 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Southwest
8.0
Very good
4,295 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
KLM
7.8
Good
1,333 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.
Copa Airlines
7.5
Good
1,411 reviews
Japan Airlines
8.3
Very good
1,459 reviews

Crew

8.7

Entertainment

7.8

Boarding

8.4

Comfort

8.2

Food

7.7

Overall

8.3

Reviews

1 / 20
8.0
Excellent

Anonymous,Nov 2024

HKG - NRT

Online check in and seat selection was tricky. Also I received some emails from Japan Airlines in Japanese with no English selection which worried me. I still don’t know what they said. The service at check in and onboard was very courteous and polite, and staff was helpful.

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 Spirit Airlines. According to our data, you can fly for as low as $76. Users have also found prices from $82 and $103 on Frontier and United 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 December is currently the most expensive (average of $336). 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

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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 April 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$262FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$91Average$400FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$133Average$291FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$179Average$549FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$541FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$552FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$277Average$587FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$303Average$724FlexibilityNo cancel feeOn-time63%

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