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Caribbean

$73+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Jun 18 — Jun 251
Thu 6/18
Thu 6/25
1 adult, Economy
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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 May 19, 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

Sat 6/20

3:11 pm-2:15 pm

1 stop24h 04m

Medellín Jose Maria Cordova Intl

Sat 6/27

5:00 am-12:47 pm

1 stop6h 47m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 6/14

6:17 pm-9:40 am

1 stop16h 23m

Medellín Jose Maria Cordova Intl

Fri 6/19

6:20 pm-12:47 pm

1 stop17h 27m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 9/7

11:35 am-1:20 pm

Nonstop2h 45m

Medellín Jose Maria Cordova Intl

Sat 9/12

3:20 pm-7:08 pm

Nonstop2h 48m

$221

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Tue 7/7

5:22 pm-8:30 pm

Nonstop3h 08m

Tampa

Mon 7/13

9:35 pm-12:41 am

Nonstop3h 06m

$266

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 6/26

3:11 pm-10:55 am

1 stop20h 44m

Medellín Jose Maria Cordova Intl

Mon 6/29

12:40 pm-12:47 pm

1 stop23h 07m

$297

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 6/15

6:17 pm-2:45 pm

1 stop21h 28m

Medellín Jose Maria Cordova Intl

Wed 6/24

4:30 pm-4:14 pm

1 stop22h 44m

$297

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 7/31

3:11 pm-8:15 am

1 stop18h 04m

Medellín Jose Maria Cordova Intl

Mon 8/3

4:30 pm-4:14 pm

1 stop22h 44m

$300

Santo DomingoNewark

SDQ - EWR

SDQEWR

Santo Domingo Las Americas

Sat 10/3

6:10 am-10:30 am

Nonstop4h 20m

Newark

Mon 10/12

12:00 pm-4:30 pm

Nonstop4h 30m

$307

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Tue 8/18

7:30 am-11:25 am

Nonstop3h 55m

New York John F Kennedy Intl

Mon 8/24

12:40 pm-4:33 pm

Nonstop3h 53m

$322

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 9/17

4:55 pm-9:10 pm

2 stops29h 15m

Medellín Jose Maria Cordova Intl

Mon 9/21

9:45 am-2:44 pm

2 stops27h 59m

$322

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/16

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.

When is the best time to book a flight from Caribbean?

To ensure you get the cheapest price possible for a flight from Caribbean, you should look to book at least 31 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, February is the cheapest month in which you can book a flight from Caribbean (average of $218). Flying from Caribbean in December will prove the most costly (average of $317). 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 May 16, 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 $101
Frontier
Frontier
From $33

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 $29. Explore other affordable destinations below.

Scarborough ANR Robinson Intl
Scarborough ANR Robinson Intl
From $29
Port of Spain Piarco Intl
Port of Spain Piarco Intl
From $31
Jacksonville
Jacksonville
From $50
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 May 19, 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
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
7.9
Good
4,284 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
JetBlue
7.2
Good
2,983 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Spirit Airlines
6.2
Okay
8,614 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Bahamasair
5.8
Fair
65 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Frontier
5.7
Fair
2,945 reviews
Southwest
7.9
Good
4,284 reviews

Comfort

8.0

Overall

7.9

Crew

8.6

Boarding

8.1

Food

7.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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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 May 19, 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 $147; whereas Aguadilla Borinquen airport is typically cheaper if you're flying to New York, from $212. 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?

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

    Check out the cheapest flights from Caribbean to embark to:
    Fly from San Juan to Punta Cana from $147 round trip
    Fly from San Juan to Santo Domingo from $173 round trip
    Fly from San Juan to Medellín from $186 round trip
    Fly from San Juan to Chicago from $192 round trip
    Fly from San Juan to Jacksonville from $205 round trip

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