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Caribbean Islands

$84+ 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 8/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
May 22 — May 291
Fri 5/22
Fri 5/29
1 adult, Economy
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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 April 22, 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 JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Thu 5/14

8:04 pm-7:30 am

1 stop11h 26m

Tampa

Mon 5/18

8:55 pm-11:57 pm

Nonstop3h 02m

$190

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 9/4

6:16 pm-8:15 am

1 stop14h 59m

Medellín Jose Maria Cordova Intl

Thu 9/10

6:25 am-10:29 pm

1 stop15h 04m

$215

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Tue 6/23

5:34 am-2:15 pm

1 stop9h 41m

Medellín Jose Maria Cordova Intl

Sat 7/4

9:15 am-4:14 pm

1 stop5h 59m

$215

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 5/17

5:27 am-8:35 pm

1 stop16h 08m

Medellín Jose Maria Cordova Intl

Fri 5/22

9:15 am-10:24 pm

1 stop12h 09m

$215

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

5:00 am-12:47 pm

1 stop6h 47m

$215

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 7/3

6:17 pm-8:15 am

1 stop14h 58m

Medellín Jose Maria Cordova Intl

Fri 7/17

5:00 am-12:47 pm

1 stop6h 47m

$215

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 9/4

6:16 pm-8:15 am

1 stop14h 59m

Medellín Jose Maria Cordova Intl

Wed 9/9

6:25 am-10:29 pm

1 stop15h 04m

$221

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 5/11

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Mon 5/18

8:35 am-4:09 pm

1 stop6h 34m

$249

San JuanNewark

SJU - EWR

SJUEWR

San Juan Luis Munoz Marin Intl

Fri 6/5

8:30 am-12:34 pm

Nonstop4h 04m

Newark

Sun 6/7

8:55 am-12:58 pm

Nonstop4h 03m

$259

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Wed 5/13

2:56 pm-6:17 pm

Nonstop3h 21m

Tampa

Mon 5/18

8:55 pm-11:57 pm

Nonstop3h 02m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

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, September is the cheapest month in which you can book a flight from Caribbean Islands (average of $245). Flying from Caribbean Islands in December will prove the most costly (average of $378). 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 April 18, 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 Tuesday 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
Copa Airlines
Copa Airlines
From $101
Frontier
Frontier
From $31

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 April 22, 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.
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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.
JetBlue
7.2
Good
2,950 reviews
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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.
American Airlines
7.1
Good
11,659 reviews
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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.
Spirit Airlines
6.3
Okay
8,634 reviews
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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.
Bahamasair
5.8
Fair
66 reviews
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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.
Frontier
5.7
Fair
2,981 reviews
JetBlue
7.2
Good
2,950 reviews

Food

6.6

Crew

7.9

Overall

7.2

Entertainment

7.2

Comfort

7.5

Boarding

7.3

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 April 22, 2026.

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

    Istanbul airport offers the cheapest routes to Boston, 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?

    September is currently the cheapest month to fly from Caribbean Islands. At this moment in time December 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 Medellín to Cartagena from $24 round trip
    Fly from Cheongju to Jeju City from $24 round trip
    Fly from Cartagena to Medellín from $25 round trip
    Fly from Medellín to Santa Marta from $34 round trip

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