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$63+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Apr 7 — Apr 141
Mon 4/7
Mon 4/14
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 2, 2025.

Round-trip from

$125
(Frontier)

One-way from

$63
(Cheapflightsfares)

Good round-trip deal

$175 or less

Good one-way deal

$127 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 2, 2025.

This Justfly.com deal was found by Cheapflights users on 3/31. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/294:00 pmEWR - SJU
1 stop16h 26mMultiple Airlines
Fri 5/96:15 amSJU - EWR
Nonstop4h 07mMultiple Airlines
Deal found 3/31$119
This Frontier deal was found by Cheapflights users on 4/1. 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.
Wed 5/76:00 amJFK - SJU
Nonstop4h 00mFrontier
Wed 5/79:30 pmSJU - JFK
Nonstop4h 05mFrontier
Deal found 4/1$125
This eDestinos deal was found by Cheapflights users on 4/1. 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.
Wed 4/3011:25 amEWR - SJU
Nonstop3h 50mFrontier
Wed 5/76:15 amSJU - EWR
Nonstop4h 07mFrontier
Deal found 4/1$129
This Mytrip deal was found by Cheapflights users on 3/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/294:00 pmEWR - SJU
1 stop16h 26mSpirit Airlines
Tue 5/63:41 pmSJU - EWR
1 stop7h 25mSpirit Airlines
Deal found 3/30$134
This JetBlue Airways deal was found by Cheapflights users on 4/1. 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 Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/295:30 pmJFK - SJU
Nonstop3h 58mJetBlue
Tue 4/293:28 amSJU - JFK
Nonstop4h 01mJetBlue
Deal found 4/1$171
This Cheapflightsfares deal was found by Cheapflights users on 3/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/306:00 amLGA - SJU
1 stop9h 35mSpirit Airlines
Tue 5/61:33 amSJU - LGA
1 stop13h 27mSpirit Airlines
Deal found 3/30$183
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/107:53 pmEWR - SJU
Nonstop4h 04mUnited Airlines
Tue 5/131:05 amSJU - EWR
Nonstop4h 09mUnited Airlines
Deal found 3/31$186
This United Airlines deal was found by Cheapflights users on 3/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/91:15 pmLGA - SJU
1 stop10h 39mUnited Airlines
Thu 4/107:45 amSJU - LGA
1 stop9h 30mUnited Airlines
Deal found 3/31$190
This American Airlines deal was found by Cheapflights users on 3/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/73:55 pmLGA - SJU
1 stop8h 14mAmerican Airlines
Thu 4/105:30 amSJU - LGA
1 stop6h 37mAmerican Airlines
Deal found 3/31$195
This Delta deal was found by Cheapflights users on 3/31. 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.
Fri 9/196:40 pmJFK - SJU
Nonstop4h 02mDelta
Mon 9/227:00 amSJU - JFK
Nonstop3h 50mDelta
Deal found 3/31$218
This JetBlue deal was found by Cheapflights users on 4/1. 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 5/99:45 pmEWR - SJU
Nonstop4h 01mJetBlue
Tue 5/1310:40 pmSJU - EWR
Nonstop4h 06mJetBlue
Deal found 4/1$218
This Delta deal was found by Cheapflights users on 4/1. 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.
Wed 5/75:59 amEWR - SJU
1 stop6h 46mDelta
Sat 5/105:43 pmSJU - EWR
1 stop7h 24mDelta
Deal found 4/1$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 2, 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

Tue 4/29

4:00 pm-8:26 am

1 stop16h 26m

San Juan Luis Munoz Marin Intl

Fri 5/9

6:15 am-10:22 am

Nonstop4h 07m

$119

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 5/7

6:00 am-10:00 am

Nonstop4h 00m

San Juan Luis Munoz Marin Intl

Wed 5/7

9:30 pm-1:35 am

Nonstop4h 05m

$125

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Wed 4/30

11:25 am-3:15 pm

Nonstop3h 50m

San Juan Luis Munoz Marin Intl

Wed 5/7

6:15 am-10:22 am

Nonstop4h 07m

$129

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 4/29

4:00 pm-8:26 am

1 stop16h 26m

San Juan Luis Munoz Marin Intl

Tue 5/6

3:41 pm-11:06 pm

1 stop7h 25m

$134

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 4/29

3:30 pm-7:34 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Tue 4/29

3:28 am-7:29 am

Nonstop4h 01m

$171

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Wed 4/30

6:00 am-3:35 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Tue 5/6

1:33 am-3:00 pm

1 stop13h 27m

$183

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sat 5/10

7:53 pm-11:57 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Tue 5/13

1:05 am-5:14 am

Nonstop4h 09m

$186

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Wed 4/9

1:15 pm-11:54 pm

1 stop10h 39m

San Juan Luis Munoz Marin Intl

Thu 4/10

7:45 am-5:15 pm

1 stop9h 30m

$190

New YorkSan Juan

LGA - SJU

LGASJU

New York LaGuardia

Mon 4/7

3:55 pm-12:09 am

1 stop8h 14m

San Juan Luis Munoz Marin Intl

Thu 4/10

5:30 am-12:07 pm

1 stop6h 37m

$195

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 4/4

7:29 am-8:20 pm

1 stop12h 51m

San Juan Luis Munoz Marin Intl

Tue 4/8

6:05 am-5:30 pm

1 stop11h 25m

$220

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

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 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 2, 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 2, 2025.
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,272 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,898 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,615 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,272 reviews

Entertainment

7.6

Overall

8.0

Crew

8.6

Food

7.1

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $63. Users have also found prices from $63 and $88 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 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

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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.
Newark to Cancún flights
Newark to Fort Lauderdale flights
John F Kennedy Intl to Miami flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
Newark to Miami flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Cancún flights
John F Kennedy Intl to Heathrow flights
Los Angeles to Haneda flights
Newark to Orlando flights
Los Angeles to John F Kennedy Intl flights
LaGuardia to Orlando flights
LaGuardia to Dallas/Fort Worth flights
Newark to Heathrow flights
John F Kennedy Intl to Las Vegas flights
John F Kennedy Intl to Charles de Gaulle flights
Dallas/Fort Worth to Seattle flights
John F Kennedy Intl to Fort Lauderdale flights
Newark to Las Vegas flights
John F Kennedy Intl to Orlando flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Cancún flights
John F Kennedy Intl to Haneda flights
John F Kennedy Intl to Gatwick flights
Los Angeles to Narita flights
Newark to Charles de Gaulle flights
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Leonardo da Vinci/Fiumicino flights
O'Hare Intl to Cancún flights
San Francisco to John F Kennedy Intl flights
LaGuardia to O'Hare Intl flights
Dallas/Fort Worth to O'Hare Intl flights
John F Kennedy Intl to Seattle flights
Newark to Seattle flights
LaGuardia to Atlanta flights
Newark to Haneda flights
Newark to Dallas/Fort Worth flights
John F Kennedy Intl to West Palm Beach flights
Newark to Leonardo da Vinci/Fiumicino flights
Dallas/Fort Worth to Las Vegas flights
Newark to Narita flights
Los Angeles to Honolulu flights
Newark to Los Angeles flights
Los Angeles to Newark flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
Newark to Tampa flights
George Bush Intcntl to Cancún flights
O'Hare Intl to John F Kennedy Intl flights
LaGuardia to Los Angeles 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 April 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$258FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$91Average$445FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$126Average$546FlexibilityNo cancel feeOn-time62%
Avelo AirlinesCheapest$133Average$292FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$197Average$537FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$207Average$580FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$277Average$593FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$303Average$735FlexibilityNo cancel feeOn-time63%

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