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Caribbean

$83+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
May 16 — May 231
Sat 5/16
Sat 5/23
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 April 16, 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 4/22

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Wed 4/29

9:15 am-4:09 pm

1 stop5h 54m

$222

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Tue 6/2

6:17 pm-8:15 am

1 stop14h 58m

Medellín Jose Maria Cordova Intl

Tue 7/7

8:35 am-4:14 pm

1 stop6h 39m

$233

San JuanNewark

SJU - EWR

SJUEWR

San Juan Luis Munoz Marin Intl

Fri 5/22

8:04 pm-8:59 am

1 stop12h 55m

Newark

Sun 5/24

7:00 am-4:52 pm

1 stop9h 52m

$244

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Fri 6/19

5:15 pm-8:30 pm

Nonstop3h 15m

Tampa

Tue 6/23

9:35 pm-12:37 am

Nonstop3h 02m

$254

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 5/25

6:12 pm-8:15 am

1 stop15h 03m

Medellín Jose Maria Cordova Intl

Fri 5/29

9:15 am-4:09 pm

1 stop5h 54m

$255

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Fri 4/24

3:37 pm-11:02 pm

1 stop7h 25m

Tampa

Tue 4/28

6:35 am-9:30 am

Nonstop2h 55m

$285

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Fri 5/1

2:45 pm-11:16 pm

1 stop8h 31m

Tampa

Tue 5/5

11:00 am-8:24 pm

1 stop9h 24m

$286

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Wed 7/1

7:05 am-11:01 am

Nonstop3h 56m

New York John F Kennedy Intl

Tue 7/7

7:29 pm-11:53 pm

Nonstop4h 24m

$302

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Thu 5/14

11:23 am-7:30 am

2 stops20h 07m

Tampa

Sun 5/17

8:25 am-10:18 am

2 stops25h 53m

$304

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 6/29

5:34 am-2:15 pm

1 stop9h 41m

Medellín Jose Maria Cordova Intl

Thu 7/2

8:35 am-4:14 pm

1 stop6h 39m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/15

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 April 11, 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 Tuesday 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 Port of Spain Piarco Intl, with prices starting at $28. Explore other affordable destinations below.

Port of Spain Piarco Intl
Port of Spain Piarco Intl
From $28
Scarborough ANR Robinson Intl
Scarborough ANR Robinson Intl
From $31
Medellín Jose Maria Cordova Intl
Medellín Jose Maria Cordova Intl
From $32
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 April 16, 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
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
8.0
Very good
4,329 reviews
Southwest
8.0
Very good
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
2,938 reviews
Southwest
8.0
Very good
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
6.3
Okay
8,616 reviews
Southwest
8.0
Very good
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
66 reviews
Southwest
8.0
Very good
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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
2,988 reviews
Southwest
8.0
Very good
4,329 reviews

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Crew

8.6

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 April 16, 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 $71; whereas Ponce Mercedita airport is typically cheaper if you're flying to Orlando, from $186. 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 Orlando from $71 round trip
    Fly from San Juan to New York from $84 round trip
    Fly from San Juan to Atlanta from $115 round trip
    Fly from San Juan to Miami from $119 round trip
    Fly from San Juan to Fort Lauderdale from $121 round trip

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