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Caribbean Islands

$83+ Cheap flights from Connecticut to Caribbean Islands

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 11/1. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
Aug 30 — Sep 61
Sat 8/30
Sat 9/6
1 adult, Economy
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Cheap flight deals from Connecticut to Caribbean Islands

Keep the following information in mind while searching for Connecticut to Caribbean Islands flight deals. Data was last updated August 25, 2025.

Round-trip from

$146
(Cheapflightsfares)

One-way from

$83
(CheapOair)

Popular in

December

Cheapest in

January

Average price

$327
From Connecticut to Caribbean Islands
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One-way flight from Connecticut to Caribbean Islands
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High demand for flights, 1% potential price rise
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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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Find flight deals from Connecticut to Caribbean Islands

Cheapest flights from Connecticut to Caribbean Islands
Explore the most affordable flight options available from Connecticut to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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.
Mon 9/810:00 pmEWR - SJU
Nonstop3h 58mFrontier
Sat 9/274:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/23$146
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 9/1610:00 pmEWR - SJU
Nonstop3h 58mFrontier
Sat 9/204:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/23$147
This Frontier deal was found by Cheapflights users on 8/22. 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.
Sat 9/1310:00 pmEWR - SJU
Nonstop3h 58mFrontier
Thu 9/184:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/22$148
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/2210:00 pmEWR - SJU
Nonstop3h 58mFrontier
Tue 9/234:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/24$150
This Kiwi.com deal was found by Cheapflights users on 8/23. 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.
Wed 9/2410:00 pmEWR - SJU
Nonstop3h 58mFrontier
Tue 9/304:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/23$151
This Cheapflightsfares deal was found by Cheapflights users on 8/23. 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 9/1610:00 pmEWR - SJU
Nonstop3h 58mFrontier
Tue 9/234:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/23$152
This Cheapflightsfares deal was found by Cheapflights users on 8/24. 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.
Sat 9/1310:00 pmEWR - SJU
Nonstop3h 58mFrontier
Fri 9/194:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/24$153
This Justfly.com deal was found by Cheapflights users on 8/25. 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.
Sat 9/208:25 pmEWR - SJU
1 stop17h 18mMultiple Airlines
Tue 9/234:51 pmSJU - EWR
Nonstop4h 11mMultiple Airlines
Deal found 8/25$154
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sat 9/138:25 pmEWR - SJU
1 stop17h 18mMultiple Airlines
Thu 9/184:51 pmSJU - EWR
Nonstop4h 11mMultiple Airlines
Deal found 8/24$155
This Kiwi.com deal was found by Cheapflights users on 8/24. 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.
Sat 9/1310:00 pmEWR - SJU
Nonstop3h 58mFrontier
Sat 9/204:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/24$156
This Kiwi.com deal was found by Cheapflights users on 8/24. 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 9/156:00 amJFK - SJU
Nonstop3h 56mFrontier
Tue 9/239:26 pmSJU - JFK
Nonstop3h 59mFrontier
Deal found 8/24$157
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/1510:00 pmEWR - SJU
Nonstop3h 58mFrontier
Fri 9/194:51 pmSJU - EWR
Nonstop4h 11mFrontier
Deal found 8/22$157

Cheapflights Fare Finder

 
Customize your flight search to find flights from Connecticut to Caribbean Islands 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 25, 2025.
Use the filters below to find and compare flights from Connecticut to Caribbean Islands that are best for you.

Fly from

Connecticut

Fly to

Caribbean Islands

Route

Depart

Return

Price

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 9/22

6:00 am-9:56 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Mon 9/29

9:26 pm-1:25 am

Nonstop3h 59m

$160

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Fri 10/10

11:30 am-3:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Wed 10/15

6:22 am-10:25 am

Nonstop4h 03m

$162

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 10/19

11:30 am-3:24 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Sun 10/26

6:22 am-10:25 am

Nonstop4h 03m

$162

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 9/15

6:00 am-9:56 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Fri 9/19

9:26 pm-1:25 am

Nonstop3h 59m

$167

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 9/20

5:00 pm-8:59 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Sun 9/21

6:00 am-9:57 am

Nonstop3h 57m

$171

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 9/17

5:25 pm-9:24 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Thu 9/18

6:00 am-9:57 am

Nonstop3h 57m

$171

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 9/27

6:00 am-9:56 am

Nonstop3h 56m

San Juan Luis Munoz Marin Intl

Fri 10/3

9:26 pm-1:25 am

Nonstop3h 59m

$171

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 11/15

1:00 pm-5:54 pm

Nonstop3h 54m

San Juan Luis Munoz Marin Intl

Mon 11/17

9:00 am-12:03 pm

Nonstop4h 03m

$173

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Thu 10/2

12:25 pm-4:17 pm

Nonstop3h 52m

San Juan Luis Munoz Marin Intl

Sat 10/4

6:00 pm-10:10 pm

Nonstop4h 10m

$176

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Sun 10/5

7:55 am-12:00 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Sat 10/11

6:40 pm-10:50 pm

Nonstop4h 10m

$176

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/24

Showing 1-10 of 60 results
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Best time to book a flight from Connecticut to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

What is the cheapest month to book a flight from Connecticut to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $254). Flying from Connecticut to Caribbean Islands 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 EPX?

Find hourly flight availability from Connecticut to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 25, 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 Islands as you normally would.

Weekly flight availability from Connecticut to Caribbean Islands

Explore weekly flight availability from Connecticut to Caribbean Islands. 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 25, 2025.

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

Related info for your journey

Find useful and relevant information for your journey from Connecticut to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Connecticut to Caribbean Islands?

    There are many flights that can get you from Connecticut to Caribbean Islands in 3h 56m. Fly via Frontier, United Airlines, or Spirit Airlines to get the fastest option. Airlines will cover a distance of 1601 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Connecticut to Caribbean Islands one-way?

    One-way options have recently been found by users for as low as $83 on Frontier. Other airlines that offer cheap prices include JetBlue from $92 and Spirit Airlines from $92 one-way.

  • Can I find deals for flights from Connecticut to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on Connecticut to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Connecticut to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Connecticut to Caribbean Islands.

  • Can I find deals for business class flights from Connecticut to Caribbean Islands?

    Yes. Cheapflights offers flight deals from Connecticut to Caribbean Islands 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 Islands?

    Currently, September is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $254). Flying from Connecticut to Caribbean Islands 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

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Alternative routes for Connecticut to Caribbean Islands

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 Islands

Discover the top 8 airlines that operate flights from Connecticut to Caribbean Islands. 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$316FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$100Average$379FlexibilityNo cancel feeOn-time65%
Avelo AirlinesCheapest$116Average$294FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$186Average$524FlexibilityNo cancel feeOn-time62%
DeltaCheapest$197Average$581FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$228Average$555FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$262Average$702FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$277Average$590FlexibilityNo cancel feeOn-time71%

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