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Caribbean Islands

$76+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
BDL — SJU
May 11 — May 181
Mon 5/11
Mon 5/18
1 adult, Economy
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Cheap 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 April 11, 2026.

This CheapOair deal was found by Cheapflights users on 4/6. 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.
Sun 5/106:42 pm
EWR
-
SJU
Nonstop4h 00m
Multiple Airlines
Thu 5/145:15 pm
SJU
-
EWR
1 stop8h 03m
Multiple Airlines
Deal found 4/6$213
This Cheapflightsfares deal was found by Cheapflights users on 4/7. 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 4/195:59 am
EWR
-
SJU
1 stop8h 09m
Frontier
Tue 4/283:08 am
SJU
-
EWR
1 stop9h 51m
Frontier
Deal found 4/7$214
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 4/215:05 pm
EWR
-
SJU
1 stop6h 19m
Multiple Airlines
Sat 4/253:43 pm
SJU
-
EWR
1 stop9h 33m
Multiple Airlines
Deal found 4/9$215
This Priceline deal was found by Cheapflights users on 4/6. 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.
Fri 5/811:30 am
EWR
-
SJU
1 stop14h 38m
Multiple Airlines
Mon 5/1112:59 am
SJU
-
EWR
Nonstop4h 07m
Multiple Airlines
Deal found 4/6$216
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 4/1311:30 am
EWR
-
SJU
Nonstop4h 00m
Multiple Airlines
Wed 4/2210:50 am
SJU
-
EWR
Nonstop4h 10m
Multiple Airlines
Deal found 4/7$217
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/611:30 am
EWR
-
SJU
1 stop11h 13m
Multiple Airlines
Thu 5/1412:59 am
SJU
-
EWR
Nonstop4h 07m
Multiple Airlines
Deal found 4/6$218
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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.
Fri 4/249:00 pm
EWR
-
SJU
1 stop12h 19m
Spirit Airlines
Sat 5/210:50 am
SJU
-
EWR
Nonstop4h 10m
Spirit Airlines
Deal found 4/6$219
This CheapOair deal was found by Cheapflights users on 4/8. 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.
Wed 5/276:42 pm
EWR
-
SJU
Nonstop4h 00m
Spirit Airlines
Mon 6/18:04 pm
SJU
-
EWR
1 stop12h 55m
Spirit Airlines
Deal found 4/8$220
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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 5/96:00 am
EWR
-
SJU
1 stop12h 59m
Spirit Airlines
Fri 5/1512:59 am
SJU
-
EWR
Nonstop4h 07m
Spirit Airlines
Deal found 4/6$221
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fri 5/86:42 pm
EWR
-
SJU
Nonstop4h 00m
Multiple Airlines
Sat 5/163:03 am
SJU
-
EWR
1 stop7h 29m
Multiple Airlines
Deal found 4/9$222
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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.
Fri 6/51:30 pm
EWR
-
SJU
1 stop15h 19m
Frontier
Wed 6/105:15 pm
SJU
-
EWR
1 stop7h 50m
Frontier
Deal found 4/6$223
This Cheapflightsfares deal was found by Cheapflights users on 4/6. 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.
Fri 4/1011:30 am
EWR
-
SJU
Nonstop4h 00m
Frontier
Fri 4/173:23 pm
SJU
-
EWR
1 stop9h 53m
Frontier
Deal found 4/6$224

Find 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 April 11, 2026.

Round-trip from

$213
(CheapOair)

One-way from

$76
(Booking.com)

Popular in

December

Cheapest in

January

Average price

$366
From Connecticut to Caribbean Islands
Search Deals
One-way flight from Connecticut to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($4 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

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 April 11, 2026.
Use the filters below to find and compare flights from Connecticut to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sun 6/14

12:30 pm-4:29 pm

Nonstop3h 59m

San Juan Luis Munoz Marin Intl

Tue 6/23

1:10 pm-5:19 pm

Nonstop4h 09m

$292

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 4/20

12:29 pm-4:31 pm

Nonstop4h 02m

San Juan Luis Munoz Marin Intl

Sat 4/25

7:15 am-11:18 am

Nonstop4h 03m

$297

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 7/8

7:29 pm-11:53 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Wed 7/15

7:35 am-11:30 am

Nonstop3h 55m

$302

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Sat 5/30

7:20 pm-11:35 pm

Nonstop4h 15m

San Juan Luis Munoz Marin Intl

Sat 6/6

7:05 am-11:03 am

Nonstop3h 58m

$307
Quickest round-trip

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 4/28

4:59 pm-9:00 pm

Nonstop4h 01m

San Juan Luis Munoz Marin Intl

Sat 5/2

6:20 am-10:20 am

Nonstop4h 00m

$322

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Wed 4/22

8:05 am-12:12 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Tue 4/28

7:15 am-11:18 am

Nonstop4h 03m

$322

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Mon 4/20

8:05 am-12:12 pm

Nonstop4h 07m

San Juan Luis Munoz Marin Intl

Wed 4/22

7:15 am-11:18 am

Nonstop4h 03m

$322

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Tue 5/5

8:00 am-12:04 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Fri 5/8

1:00 am-5:10 am

Nonstop4h 10m

$327

NewarkSan Juan

EWR - SJU

EWRSJU

Newark

Fri 6/12

7:45 pm-11:50 pm

Nonstop4h 05m

San Juan Luis Munoz Marin Intl

Tue 6/16

6:45 pm-10:55 pm

Nonstop4h 10m

$327

New YorkSan Juan

JFK - SJU

JFKSJU

New York John F Kennedy Intl

Tue 5/12

12:25 pm-4:29 pm

Nonstop4h 04m

San Juan Luis Munoz Marin Intl

Sat 5/23

7:05 am-11:03 am

Nonstop3h 58m

$327

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/10

Showing 1-10 of 60 resultsSorted by cheapest first
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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, April is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $101). Flying from Connecticut to Caribbean Islands in September is currently the most expensive (average of $163). 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 April 11, 2026.

One of the essential ways to save on airfare from Connecticut to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 20% on airfare.

What is the cheapest day to fly from Connecticut to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Connecticut to Caribbean Islands. Price data was last updated on April 4, 2026.

Travelers seeking maximum savings on their Connecticut to Caribbean Islands flight should consider departing on Wednesday at noon when fares are most often at their lowest. Friday evenings flights should be avoided if possible as fares are typically the most expensive at this time.

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 April 11, 2026.

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 59m. Fly via Delta, United Airlines, or Southwest 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 $66 on Frontier. Other airlines that offer cheap prices include JetBlue from $86 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, April is the cheapest month in which you can book a flight from Connecticut to Caribbean Islands (average of $101). Flying from Connecticut to Caribbean Islands in September is currently the most expensive (average of $163). 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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John F Kennedy Intl to San Francisco flights
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San Francisco to Seattle flights
Los Angeles to San Francisco flights
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O'Hare Intl to Seattle flights
Los Angeles to O'Hare Intl flights

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 April 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$100Average$330FlexibilityNo cancel feeOn-time65%
FrontierCheapest$101Average$339FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$110Average$462FlexibilityNo cancel feeOn-time69%
Avelo AirlinesCheapest$112Average$323FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$150Average$456FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$205Average$476FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$262Average$610FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$263Average$574FlexibilityNo cancel feeOn-time71%

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