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Caribbean Islands

$54+ Cheap flights from 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 3/5. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — JFK
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Find flights from Caribbean Islands

Cheapest flights from Caribbean Islands
Explore the most affordable flight options available from Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/9. 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 1/166:10 pmSJU - EWR
Nonstop4h 20mFrontier
Sun 1/2511:30 amEWR - SJU
Nonstop3h 55mFrontier
Deal found 12/9$105
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
Thu 1/227:10 amSJU - EWR
Nonstop4h 20mFrontier
Sun 1/2511:30 amEWR - SJU
Nonstop3h 55mFrontier
Deal found 12/11$106
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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 1/234:22 pmSJU - EWR
1 stop9h 46mFrontier
Tue 1/2711:30 amEWR - SJU
Nonstop3h 55mFrontier
Deal found 12/11$111
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Sat 1/246:11 pmSJU - EWR
1 stop7h 57mFrontier
Tue 1/2711:30 amEWR - SJU
Nonstop3h 55mFrontier
Deal found 12/10$112
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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 1/246:11 pmSJU - EWR
1 stop7h 57mFrontier
Mon 1/266:00 amEWR - SJU
1 stop8h 12mFrontier
Deal found 12/11$116
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Sat 1/3111:49 amSJU - EWR
1 stop14h 19mFrontier
Mon 2/26:00 amEWR - SJU
1 stop8h 12mFrontier
Deal found 12/10$117
This Kiwi.com deal was found by Cheapflights users on 12/9. 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 1/304:22 pmSJU - EWR
1 stop9h 46mFrontier
Sun 2/111:30 amEWR - SJU
Nonstop3h 55mFrontier
Deal found 12/9$119
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2111:45 amSJU - JFK
Nonstop4h 15mFrontier
Wed 12/311:00 pmJFK - SJU
Nonstop3h 54mFrontier
Deal found 12/10$121
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 1/165:50 pmSJU - EWR
Nonstop4h 15mMultiple Airlines
Sun 1/2511:30 amEWR - SJU
Nonstop3h 55mMultiple Airlines
Deal found 12/10$122
This Trip.com deal was found by Cheapflights users on 12/10. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/298:15 amSJU - JFK
Nonstop4h 03mMultiple Airlines
Sat 1/311:00 pmJFK - SJU
Nonstop3h 58mMultiple Airlines
Deal found 12/10$122
This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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 2/157:10 amSJU - EWR
Nonstop4h 25mFrontier
Sat 2/2111:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 12/11$123
This Kiwi.com deal was found by Cheapflights users on 12/11. 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.
Thu 1/298:50 amSJU - JFK
Nonstop4h 14mFrontier
Sat 1/311:00 pmJFK - SJU
Nonstop3h 58mFrontier
Deal found 12/11$123

Find flights from Caribbean Islands within your budget

 
Find flights departing from Caribbean Islands that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on December 12, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

John F Kennedy Intl

Route

Depart

Return

Price

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 2/2

6:14 pm-8:18 am

1 stop15h 04m

Medellín Jose Maria Cordova Intl

Fri 2/6

12:42 pm-10:32 pm

1 stop8h 50m

$168

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 1/31

5:37 am-9:51 am

1 stop5h 14m

Medellín Jose Maria Cordova Intl

Wed 2/4

9:17 am-10:32 pm

1 stop12h 15m

$168

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 1/30

6:14 pm-8:18 am

1 stop15h 04m

Medellín Jose Maria Cordova Intl

Wed 2/4

10:46 am-10:32 pm

1 stop10h 46m

$168

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 1/31

5:37 am-9:51 am

1 stop5h 14m

Medellín Jose Maria Cordova Intl

Tue 2/3

10:46 am-10:32 pm

1 stop10h 46m

$168

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Tue 3/3

5:37 am-2:15 pm

1 stop9h 38m

Medellín Jose Maria Cordova Intl

Wed 3/11

4:30 pm-10:29 pm

1 stop4h 59m

$168

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 3/7

6:14 pm-8:18 am

1 stop15h 04m

Medellín Jose Maria Cordova Intl

Fri 3/13

9:17 am-10:29 pm

1 stop12h 12m

$168

San JuanOrlando

SJU - MCO

SJUMCO

San Juan Luis Munoz Marin Intl

Sat 1/24

6:00 am-8:15 am

Nonstop3h 15m

Orlando

Sat 1/31

6:00 am-9:47 am

Nonstop2h 47m

$173

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Thu 2/12

11:50 pm-2:50 am

Nonstop4h 00m

New York John F Kennedy Intl

Thu 2/19

10:59 pm-3:54 am

Nonstop3h 55m

$176

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Fri 1/16

2:20 pm-5:28 pm

Nonstop4h 08m

New York John F Kennedy Intl

Mon 1/19

9:59 am-2:56 pm

Nonstop3h 57m

$176

San JuanNewark

SJU - EWR

SJUEWR

San Juan Luis Munoz Marin Intl

Thu 1/29

4:22 pm-1:08 am

1 stop9h 46m

Newark

Wed 2/4

11:44 am-11:59 pm

1 stop11h 15m

$181

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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

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

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean Islands (average of $79). Flying from Caribbean Islands in August will prove the most costly (average of $118). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to John F Kennedy Intl. Price data was last updated on December 6, 2025.

Those who are seeking the cheapest fare on flights departing from Caribbean Islands would be wise to consider leaving during Saturday afternoons when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Tuesday at noon when fares are usually the most expensive.

Which airlines fly from Caribbean Islands?

For flights departing from Caribbean Islands check dates and pricing for the following: JetBlue, Delta, Caribbean Airlines, Frontier, American Airlines. These airlines depart to the following popular destinations: New York.

JetBlue
JetBlue
From $50
American Airlines
American Airlines
From $165
Frontier
Frontier
From $13
Copa Airlines
Copa Airlines
From $96

Airline reviews for flights from Caribbean Islands

Read reviews and ratings of airlines operating flights from Caribbean Islands. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Caribbean Islands travel. Please note that the reviews are sourced from user searches and were last updated on December 12, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Peruse reviews from past customers who have flown Caribbean Airlines, Delta, and American Airlines from Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
Caribbean Airlines
8.0
Very good
209 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
Delta
7.9
Good
8,005 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
American Airlines
7.2
Good
11,049 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
JetBlue
7.2
Good
2,899 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc
Frontier
5.8
Fair
3,084 reviews
Caribbean Airlines
8.0
Very good
209 reviews

Food

6.8

Boarding

8.0

Comfort

7.8

Overall

8.0

Entertainment

6.6

Crew

8.4

Reviews

1 / 14
8.0
Excellent

Boy,Oct 2025

YYZ - POS

A few selection of caribbean foods limit the pasta dish etc

Browse thousands of different options on Cheapflights for your next trip

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Related info for your journey

Access useful and relevant information related to your journey from Caribbean Islands. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated December 12, 2025.

  • What is the cheapest airport to fly out of Caribbean Islands?

    Istanbul airport offers the cheapest routes to Toronto, from $23; whereas Cheongju airport is typically cheaper if you're flying to Jeju City, from $24. It's best to make sure you are flexible on dates to find the cheapest possible flight options for your journey.

  • What is the cheapest month to fly from Caribbean Islands?

    April is currently the cheapest month to fly from Caribbean Islands. At this moment in time August is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.

  • Where are the cheapest places to fly to from Caribbean Islands?

    Check out the cheapest flights from Caribbean Islands to embark to:
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Venice to Tirana from $30 round trip
    Fly from Bogotá to Pereira from $31 round trip
    Fly from Orlando to New York from $34 round trip

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