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Caribbean

$64+ Cheap flights from Caribbean

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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Apr 14 — Apr 211
Tue 4/14
Tue 4/21
1 adult, Economy
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What to know about flights from Caribbean

Discover essential information about flights departing from Caribbean, including flight schedules, destinations, airlines operating at the Caribbean airport, and any specific guidelines or requirements for travelers. Please note that the information is based on the most recent updates available. Data last updated March 15, 2026.

Good round-trip deal

$64 or less

Good one-way deal

$34 or less
Price to beat on a round-trip flight from Caribbean.
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Price to beat on a one-way flight from Caribbean.
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Find flights from Caribbean

Cheapest flights from Caribbean
Explore the most affordable flight options available from Caribbean. 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 3/15. 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 4/96:07 pm
SJU
-
MIA
Nonstop3h 03m
Frontier
Sun 4/1210:36 pm
MIA
-
SJU
Nonstop2h 41m
Frontier
Deal found 3/15$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 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 3/14. 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.
Tue 3/171:39 am
SJU
-
MIA
1 stop11h 08m
Spirit Airlines
Tue 3/319:25 pm
MIA
-
SJU
Nonstop2h 33m
Spirit Airlines
Deal found 3/14$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
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/158:27 pm
SJU
-
MCO
Nonstop3h 02m
Spirit Airlines
Thu 4/166:30 am
MCO
-
SJU
Nonstop2h 49m
Spirit Airlines
Deal found 3/13$174

Find flights from Caribbean within your budget

 
Find flights departing from Caribbean 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 JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Wed 4/15

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Wed 4/22

12:40 pm-10:24 pm

1 stop8h 44m

$211

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 4/16

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Tue 4/28

10:35 am-10:24 pm

1 stop10h 49m

$221

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 4/9

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Wed 4/15

12:40 pm-10:24 pm

1 stop8h 44m

$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

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 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 JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 5/2

5:27 am-9:40 am

1 stop5h 13m

Medellín Jose Maria Cordova Intl

Wed 5/6

5:00 am-4:09 pm

1 stop10h 09m

$277

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 5/2

5:27 am-2:45 pm

1 stop10h 18m

Medellín Jose Maria Cordova Intl

Sat 5/9

9:15 am-10:24 pm

1 stop12h 09m

$287

Santo DomingoNewark

SDQ - EWR

SDQEWR

Santo Domingo Las Americas

Tue 4/28

6:10 am-10:30 am

Nonstop4h 20m

Newark

Tue 5/5

12:00 pm-9:40 pm

1 stop9h 40m

$302

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Sat 5/9

5:15 am-5:00 pm

2 stops11h 45m

Miami

Sat 5/16

9:30 am-7:05 pm

1 stop9h 35m

$305

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/10

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from Caribbean

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

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

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

Currently, May is the cheapest month in which you can book a flight from Caribbean (average of $99). Flying from Caribbean 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?

Use this chart to determine the cheapest time to fly round-trip from Caribbean to Orlando. Price data was last updated on March 12, 2026.

Those who are seeking the cheapest fare on flights departing from Caribbean 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.

Which airlines fly from Caribbean?

For flights departing from Caribbean 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 $96
Frontier
Frontier
From $29

What is the cheapest place to fly to from Caribbean?

The cheapest city to fly to from Caribbean is Scarborough ANR Robinson Intl, with prices starting at $24. Explore other affordable destinations below.

Scarborough ANR Robinson Intl
Scarborough ANR Robinson Intl
From $24
Port of Spain Piarco Intl
Port of Spain Piarco Intl
From $29
Norfolk
Norfolk
From $49
Ceiba J. Aponte de la Torre
Ceiba J. Aponte de la Torre
From $57

Airline reviews for flights from Caribbean

Read reviews and ratings of airlines operating flights from Caribbean. Gain insights into the quality of service, in-flight amenities, customer experiences, and overall satisfaction to choose the best airline for your Caribbean 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.
Read through reviews of airlines servicing Caribbean, such as Southwest,JetBlue, andSpirit Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Southwest
8.0
Very good
4,318 reviews
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
JetBlue
7.2
Good
2,907 reviews
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Spirit Airlines
6.3
Okay
8,521 reviews
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Bahamasair
5.8
Fair
66 reviews
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Frontier
5.7
Fair
3,031 reviews
Southwest
8.0
Very good
4,318 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Overall

8.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..

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. 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?

    San Juan Luis Munoz Marin Intl airport offers the cheapest routes to Panama City, from $124; whereas Santo Domingo Las Americas airport is typically cheaper if you're flying to Atlanta, from $162. 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?

    May is currently the cheapest month to fly from Caribbean. 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?

    Check out the cheapest flights from Caribbean to embark to:
    Fly from San Juan to Punta Cana from $124 round trip
    Fly from San Juan to Miami from $129 round trip
    Fly from San Juan to Santo Domingo from $132 round trip
    Fly from San Juan to Fort Lauderdale from $134 round trip
    Fly from San Juan to Atlanta from $160 round trip

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