Caribbean Islands

$64+ 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 4/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Apr 14 — Apr 211
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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 March 15, 2026.

This eDestinos deal was found by Cheapflights users on 3/13. 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.
Fri 4/36:07 pm
SJU
-
MIA
Nonstop3h 03m
Frontier
Mon 4/139:10 pm
MIA
-
SJU
Nonstop2h 43m
Frontier
Deal found 3/13$124
This eDestinos deal was found by Cheapflights users on 3/14. 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 4/96:00 am
SJU
-
MIA
Nonstop3h 00m
Frontier
Tue 4/143:24 pm
MIA
-
SJU
Nonstop2h 35m
Frontier
Deal found 3/14$125
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Thu 4/96:07 pm
SJU
-
MIA
Nonstop3h 03m
Frontier
Mon 4/139:10 pm
MIA
-
SJU
Nonstop2h 43m
Frontier
Deal found 3/10$127
This Frontier deal was found by Cheapflights users on 3/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/96:00 am
SJU
-
MIA
Nonstop3h 00m
Frontier
Sun 4/1210:36 pm
MIA
-
SJU
Nonstop2h 41m
Frontier
Deal found 3/11$128
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/1011:03 am
SJU
-
MIA
Nonstop2h 52m
Multiple Airlines
Sun 4/123:04 pm
MIA
-
SJU
Nonstop2h 35m
Multiple Airlines
Deal found 3/12$129
This eDestinos deal was found by Cheapflights users on 3/13. 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 3/266:46 pm
SJU
-
MIA
Nonstop3h 01m
Frontier
Mon 3/3010:42 pm
MIA
-
SJU
Nonstop2h 39m
Frontier
Deal found 3/13$131
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 4/311:03 am
SJU
-
MIA
Nonstop2h 52m
Spirit Airlines
Tue 4/79:25 pm
MIA
-
SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/14$132
This Frontier deal was found by Cheapflights users on 3/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/36:00 am
SJU
-
MIA
Nonstop3h 00m
Frontier
Fri 4/1010:20 pm
MIA
-
SJU
Nonstop2h 41m
Frontier
Deal found 3/10$133
This Mytrip deal was found by Cheapflights users on 3/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/811:03 am
SJU
-
MIA
Nonstop2h 52m
Multiple Airlines
Tue 4/143:24 pm
MIA
-
SJU
Nonstop2h 35m
Multiple Airlines
Deal found 3/10$134
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/36:00 am
SJU
-
MIA
Nonstop3h 00m
Multiple Airlines
Fri 4/109:25 pm
MIA
-
SJU
Nonstop2h 33m
Multiple Airlines
Deal found 3/10$135
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 4/911:03 am
SJU
-
MIA
Nonstop2h 52m
Multiple Airlines
Sun 4/1210:36 pm
MIA
-
SJU
Nonstop2h 41m
Multiple Airlines
Deal found 3/14$136
This Kiwi.com deal was found by Cheapflights users on 3/10. 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 4/36:00 am
SJU
-
MIA
Nonstop3h 00m
Frontier
Fri 4/310:20 pm
MIA
-
SJU
Nonstop2h 41m
Frontier
Deal found 3/10$137

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 March 15, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Fri 4/17

7:00 am-9:46 am

Nonstop2h 46m

Miami

Mon 4/20

12:53 pm-2:01 am

2 stops13h 08m

$228

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 4/24

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Wed 4/29

10:35 am-10:24 pm

1 stop10h 49m

$249

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Thu 3/26

12:05 pm-8:07 pm

1 stop8h 02m

Miami

Tue 3/31

8:35 pm-11:07 am

1 stop14h 32m

$264

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 7/24

3:11 pm-8:35 pm

1 stop6h 24m

Medellín Jose Maria Cordova Intl

Fri 7/31

5:00 am-12:47 pm

1 stop6h 47m

$277

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 5/28

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Tue 6/2

5:00 am-12:47 pm

1 stop6h 47m

$277

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 6/6

6:17 pm-8:15 am

1 stop14h 58m

Medellín Jose Maria Cordova Intl

Sat 6/13

5:00 am-12:47 pm

1 stop6h 47m

$277

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 7/18

6:17 pm-8:15 am

1 stop14h 58m

Medellín Jose Maria Cordova Intl

Fri 7/24

6:25 am-12:47 pm

1 stop5h 22m

$277

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Thu 5/7

10:00 am-11:00 pm

2 stops13h 00m

Miami

Fri 5/8

5:45 pm-11:55 pm

1 stop6h 10m

$284

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 5/7

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Tue 5/12

10:35 am-10:24 pm

1 stop10h 49m

$287

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 5/10

5:27 am-8:35 pm

1 stop16h 08m

Medellín Jose Maria Cordova Intl

Thu 5/14

9:15 am-10:24 pm

1 stop12h 09m

$287

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/14

Showing 1-10 of 60 resultsSorted by cheapest first
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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, May is the cheapest month in which you can book a flight from Caribbean Islands (average of $99). Flying from Caribbean Islands in October will prove the most costly (average of $131). 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 March 12, 2026.

Those who are seeking the cheapest fare on flights departing from Caribbean Islands would be wise to consider leaving during Monday mornings 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.

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 March 15, 2026. In the last 7 days, Cheapflights users made a total of 2,558,603 searches.
Peruse reviews from past customers who have flown JetBlue,American Airlines, andSpirit 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.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

Crew

8.0

Overall

7.2

Comfort

7.5

Food

6.6

Boarding

7.4

Entertainment

7.2

Reviews

1 / 20
6.0
Good

Anonymous,Mar 2026

FLL - ORH

I pay extra for an even more seat row 3, but the luggage area has no more spots so i have to place my luggage in row 10. This was totally un accepatable.

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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 March 15, 2026.
  • What is the cheapest airport to fly out of Caribbean Islands?

    Medellín Jose Maria Cordova Intl airport offers the cheapest routes to Panama City, from $22; whereas Santa Ana J. Wayne/Orange Cnty airport is typically cheaper if you're flying to Guatemala City, from $23. 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?

    May is currently the cheapest month to fly from Caribbean Islands. At this moment in time October 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 Medellín to Santa Marta from $22 round trip
    Fly from Santa Ana to Las Vegas from $23 round trip
    Fly from Medellín to Cartagena from $23 round trip
    Fly from Istanbul to Ankara from $23 round trip
    Fly from Cheongju to Jeju City from $24 round trip

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