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Caribbean Islands

$63+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

This CheapOair deal was found by Cheapflights users on 10/26. 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 1/217:10 amSJU - EWR
Nonstop4h 25mFrontier
Sat 1/2411:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/26$110
This CheapOair deal was found by Cheapflights users on 10/26. 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.
Thu 2/127:10 amSJU - EWR
Nonstop4h 25mFrontier
Fri 2/2011:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/26$114
This CheapOair deal was found by Cheapflights users on 10/27. 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 2/187:10 amSJU - EWR
Nonstop4h 25mFrontier
Wed 2/2511:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/27$116
This eDestinos deal was found by Cheapflights users on 10/28. 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.
Thu 2/57:10 amSJU - EWR
Nonstop4h 25mFrontier
Sun 2/811:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/28$118
This Priceline deal was found by Cheapflights users on 10/27. 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 2/277:10 amSJU - EWR
Nonstop4h 25mFrontier
Sun 3/111:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/27$120
This Frontier deal was found by Cheapflights users on 10/26. 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 2/147:10 amSJU - EWR
Nonstop4h 25mFrontier
Fri 2/2011:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/26$124
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/126:17 pmSJU - EWR
Nonstop4h 13mFrontier
Wed 11/1910:30 pmEWR - SJU
Nonstop4h 03mFrontier
Deal found 10/28$127
This Frontier deal was found by Cheapflights users on 10/26. 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 2/157:10 amSJU - EWR
Nonstop4h 25mFrontier
Fri 2/2011:30 amEWR - SJU
Nonstop3h 43mFrontier
Deal found 10/26$128
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/217:11 amSJU - JFK
Nonstop3h 54mFrontier
Sun 11/2311:00 amJFK - SJU
Nonstop3h 55mFrontier
Deal found 10/28$137
This Priceline deal was found by Cheapflights users on 10/26. 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 11/146:17 pmSJU - EWR
Nonstop4h 13mFrontier
Sat 11/1510:30 pmEWR - SJU
Nonstop4h 03mFrontier
Deal found 10/26$140
This Booking.com deal was found by Cheapflights users on 10/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/76:17 pmSJU - EWR
Nonstop4h 13mFrontier
Sat 11/1510:30 pmEWR - SJU
Nonstop4h 03mFrontier
Deal found 10/28$141
This Frontier deal was found by Cheapflights users on 10/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/129:00 amSJU - JFK
Nonstop4h 03mFrontier
Mon 11/176:00 amJFK - SJU
1 stop9h 10mFrontier
Deal found 10/25$146

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 October 28, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Orlando

Route

Depart

Return

Price

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 11/16

6:12 pm-8:18 am

1 stop15h 06m

Medellín Jose Maria Cordova Intl

Tue 11/25

9:17 am-4:11 pm

1 stop5h 54m

$197

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Tue 12/23

6:00 am-9:04 am

Nonstop4h 04m

New York John F Kennedy Intl

Tue 12/30

11:30 am-4:23 pm

Nonstop3h 53m

$216

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Thu 11/6

7:00 pm-10:10 pm

Nonstop4h 10m

New York John F Kennedy Intl

Mon 11/10

6:55 pm-11:56 pm

Nonstop4h 01m

$216

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Fri 11/14

6:35 pm-9:52 pm

Nonstop4h 17m

New York John F Kennedy Intl

Sun 11/16

8:00 am-12:56 pm

Nonstop3h 56m

$216

Santo DomingoMiami

SDQ - MIA

SDQMIA

Santo Domingo Las Americas

Wed 4/22

10:19 am-12:39 pm

Nonstop2h 20m

Miami

Wed 4/29

2:09 pm-4:29 pm

Nonstop2h 20m

$220

Santo DomingoMiami

SDQ - MIA

SDQMIA

Santo Domingo Las Americas

Thu 2/26

3:35 pm-4:55 pm

Nonstop2h 20m

Miami

Thu 3/5

6:25 pm-9:45 pm

Nonstop2h 20m

$220

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Wed 11/19

6:12 pm-8:18 am

1 stop15h 06m

Medellín Jose Maria Cordova Intl

Mon 11/24

9:17 am-4:11 pm

1 stop5h 54m

$220

San JuanNewark

SJU - EWR

SJUEWR

San Juan Luis Munoz Marin Intl

Fri 11/14

5:50 pm-11:38 pm

1 stop6h 48m

Newark

Sun 11/16

6:00 am-1:17 pm

1 stop6h 17m

$225

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Tue 12/2

6:11 pm-8:18 am

1 stop15h 07m

Medellín Jose Maria Cordova Intl

Wed 12/10

12:42 pm-10:25 pm

1 stop8h 43m

$226

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 11/30

6:12 pm-8:18 am

1 stop15h 06m

Medellín Jose Maria Cordova Intl

Mon 12/8

8:37 am-4:11 pm

1 stop6h 34m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

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, February is the cheapest month in which you can book a flight from Caribbean Islands (average of $85). Flying from Caribbean Islands in September will prove the most costly (average of $128). 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 Orlando. Price data was last updated on December 16, 2024.

Those who are seeking the cheapest fare on flights departing from Caribbean Islands would be wise to consider leaving during Friday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday mornings 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: Frontier, JetBlue, Spirit Airlines, Bahamasair, Southwest. These airlines depart to the following popular destinations: Orlando.

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 October 28, 2025. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Peruse reviews from past customers who have flown American Airlines, JetBlue, and Spirit 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.
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
American Airlines
7.2
Good
11,032 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
JetBlue
7.2
Good
2,908 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
Spirit Airlines
6.3
Okay
8,116 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
Frontier
5.8
Fair
3,124 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.
Bahamasair
5.7
Fair
64 reviews
American Airlines
7.2
Good
11,032 reviews

Boarding

7.5

Comfort

7.2

Crew

8.0

Entertainment

6.9

Overall

7.2

Food

6.4

Reviews

1 / 20
2.0
Mediocre

Nordia,Sep 2025

KIN - MIA

We were to land in Miami sometime after 3pm but couldn’t due to bad weather, we flew around for 2 hrs until we had to land in Forth Myers to refuel, we had to sit another 2 hrs at Forth Myers until given the clearance to refuel, we were hungry, thirsty and frustrated at that point. All the had on the flight to offer was a small plastic glass of water and a pack of biscoff, I requested a cup of tea and was told none was there. We were basically at another airport and not one of the staff could consider that the passengers might be hungry or thirsty being on a plane for around 8 hrs, which you weren’t prepared for, at least find some hot water on board.

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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 October 28, 2025.

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

    Istanbul airport offers the cheapest routes to Shanghai, 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?

    February is currently the cheapest month to fly from Caribbean Islands. At this moment in time September 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 Medellín to Montería from $27 round trip
    Fly from Larnaca to Tel Aviv from $27 round trip
    Fly from Stockholm to Luleå from $28 round trip

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