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$47+ 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$90
(Frontier)

One-way from

$47
(Trip.com)

Good round-trip deal

$186 or less

Good one-way deal

$100 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 February 22, 2025.

This Frontier deal was found by Cheapflights users on 2/22. 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.
Sun 3/26:00 amJFK - SJU
Nonstop3h 51mFrontier
Fri 3/710:44 amSJU - JFK
Nonstop4h 15mFrontier
Deal found 2/22$90
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 3/181:03 pmEWR - SJU
Nonstop3h 47mFrontier
Tue 3/259:30 pmSJU - EWR
Nonstop4h 18mFrontier
Deal found 2/21$90
This Kiwi.com deal was found by Cheapflights users on 2/21. 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.
Tue 3/47:45 amEWR - SJU
1 stop8h 16mMultiple Airlines
Fri 3/78:45 amSJU - EWR
Nonstop4h 18mMultiple Airlines
Deal found 2/21$94
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 3/255:30 amEWR - SJU
1 stop9h 21mSpirit Airlines
Wed 3/265:39 pmSJU - EWR
1 stop7h 10mSpirit Airlines
Deal found 2/21$109
This Frontier deal was found by Cheapflights users on 2/22. 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 4/15:00 pmLGA - SJU
1 stop6h 54mFrontier
Wed 4/29:35 pmSJU - LGA
1 stop13h 55mFrontier
Deal found 2/22$118
This Priceline deal was found by Cheapflights users on 2/21. 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 3/46:55 amLGA - SJU
1 stop9h 06mMultiple Airlines
Tue 3/119:35 pmSJU - LGA
1 stop12h 25mMultiple Airlines
Deal found 2/21$134
This Cheapflightsfares deal was found by Cheapflights users on 2/22. 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.
Sun 3/93:17 pmLGA - SJU
1 stop11h 06mSpirit Airlines
Thu 3/136:18 amSJU - LGA
1 stop7h 54mSpirit Airlines
Deal found 2/22$137
This Delta deal was found by Cheapflights users on 2/22. 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.
Thu 5/17:30 pmJFK - SJU
Nonstop4h 18mDelta
Mon 5/127:00 amSJU - JFK
Nonstop4h 02mDelta
Deal found 2/22$158
This United Airlines deal was found by Cheapflights users on 2/22. 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.
Sat 3/19:30 amLGA - SJU
1 stop11h 16mUnited Airlines
Wed 3/58:10 amSJU - LGA
1 stop6h 58mUnited Airlines
Deal found 2/22$167
This JetBlue deal was found by Cheapflights users on 2/21. 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.
Sat 3/228:45 pmEWR - SJU
Nonstop3h 52mJetBlue
Wed 3/268:03 pmSJU - EWR
Nonstop4h 16mJetBlue
Deal found 2/21$186
This American Airlines deal was found by Cheapflights users on 2/22. 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.
Mon 3/37:35 amJFK - SJU
1 stop15h 20mAmerican Airlines
Wed 3/125:00 amSJU - JFK
1 stop10h 58mAmerican Airlines
Deal found 2/22$192
This American Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 3/14:29 pmEWR - SJU
1 stop11h 40mAmerican Airlines
Tue 3/412:40 pmSJU - EWR
1 stop11h 20mAmerican Airlines
Deal found 2/20$192

Find flights from Connecticut to Caribbean within your budget

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 22, 2025.

Fly from

Connecticut

Fly to

Caribbean

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 3/1

3:01 pm-7:52 pm

Nonstop3h 51m

San Juan Luis Munoz Marin Intl

Thu 3/6

10:30 pm-1:45 am

Nonstop4h 15m

$90

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 3/18

1:03 pm-4:50 pm

Nonstop3h 47m

San Juan Luis Munoz Marin Intl

Tue 3/25

9:30 pm-1:48 am

Nonstop4h 18m

$90

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 3/4

7:45 am-5:01 pm

1 stop8h 16m

San Juan Luis Munoz Marin Intl

Fri 3/7

8:45 am-12:03 pm

Nonstop4h 18m

$94

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 3/25

5:30 am-2:51 pm

1 stop9h 21m

San Juan Luis Munoz Marin Intl

Wed 3/26

5:39 pm-12:49 am

1 stop7h 10m

$109

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Tue 4/1

5:00 pm-11:54 pm

1 stop6h 54m

San Juan Luis Munoz Marin Intl

Wed 4/2

9:35 pm-11:30 am

1 stop13h 55m

$118

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Tue 3/4

6:55 am-5:01 pm

1 stop9h 06m

San Juan Luis Munoz Marin Intl

Tue 3/11

9:35 pm-10:00 am

1 stop12h 25m

$134

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sun 3/9

3:17 pm-2:23 am

1 stop11h 06m

San Juan Luis Munoz Marin Intl

Thu 3/13

6:18 am-2:12 pm

1 stop7h 54m

$137

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Thu 5/1

7:30 pm-11:48 pm

Nonstop4h 18m

San Juan Luis Munoz Marin Intl

Mon 5/12

7:00 am-11:06 am

Nonstop4h 06m

$158

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Sat 3/1

9:30 am-9:46 pm

1 stop11h 16m

San Juan Luis Munoz Marin Intl

Wed 3/5

8:10 am-2:08 pm

1 stop6h 58m

$167

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 4/1

4:59 pm-8:57 pm

Nonstop3h 58m

San Juan Luis Munoz Marin Intl

Fri 4/4

12:58 am-5:00 am

Nonstop4h 02m

$186

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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.

Travel insights for flights from Connecticut to Caribbean

Get recent, data-driven insights about flights from Connecticut to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 22, 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 February 22, 2025.

The most flights from USCT to 0CB are scheduled on a Wednesday (3 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).

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 February 22, 2025.
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,395 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,203 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,502 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Aeromexico
7.5
Good
1,767 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,754 reviews
Southwest
8.1
Very good
4,395 reviews

Boarding

8.2

Entertainment

7.6

Comfort

8.1

Overall

8.1

Food

7.1

Crew

8.7

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $47. Users have also found prices from $56 and $79 on Spirit Airlines and Delta, 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 March is currently the most expensive (average of $363). 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$260FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$91Average$394FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$133Average$292FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$164Average$583FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$534FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$600FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$236Average$727FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$317Average$586FlexibilityNo cancel feeOn-time71%
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