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Caribbean

$95+ 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Aug 31 — Sep 71
Mon 8/31
Mon 9/7
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 August 1, 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

Fri 8/28

5:49 pm-12:30 am

1 stop6h 41m

Tampa

Sun 8/30

5:15 am-11:46 am

1 stop6h 31m

$236

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 8/17

6:17 pm-2:45 pm

1 stop21h 28m

Medellín Jose Maria Cordova Intl

Tue 8/25

6:20 pm-4:14 pm

1 stop20h 54m

$237

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Mon 8/24

6:17 pm-10:55 am

1 stop17h 38m

Medellín Jose Maria Cordova Intl

Wed 8/26

6:20 pm-4:14 pm

1 stop20h 54m

$237

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sat 8/22

6:17 pm-8:15 am

1 stop14h 58m

Medellín Jose Maria Cordova Intl

Tue 8/25

4:30 pm-4:14 pm

1 stop22h 44m

$237

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Sat 10/17

3:00 pm-6:56 pm

Nonstop3h 56m

New York John F Kennedy Intl

Sun 10/18

9:50 am-1:49 pm

Nonstop3h 59m

$247

San JuanNew York

SJU - JFK

SJUJFK

San Juan Luis Munoz Marin Intl

Fri 9/18

6:00 am-9:52 am

Nonstop3h 52m

New York John F Kennedy Intl

Mon 9/21

12:15 pm-4:12 pm

Nonstop3h 57m

$249
Quickest round-trip

San JuanTampa

SJU - TPA

SJUTPA

San Juan Luis Munoz Marin Intl

Fri 9/25

4:29 pm-9:14 pm

1 stop4h 45m

Tampa

Sun 9/27

1:50 pm-4:53 pm

Nonstop3h 03m

$253

San JuanOrlando

SJU - MCO

SJUMCO

San Juan Luis Munoz Marin Intl

Fri 9/4

5:30 am-4:20 pm

2 stops10h 50m

Orlando

Tue 9/8

2:55 pm-10:05 pm

1 stop7h 10m

$256

San JuanOrlando

SJU - MCO

SJUMCO

San Juan Luis Munoz Marin Intl

Thu 9/3

6:30 am-9:30 am

Nonstop3h 00m

Orlando

Mon 9/7

12:45 pm-10:55 pm

2 stops10h 10m

$260

San JuanOrlando

SJU - MCO

SJUMCO

San Juan Luis Munoz Marin Intl

Tue 9/15

6:00 am-5:55 pm

2 stops11h 55m

Orlando

Sat 9/19

1:35 pm-10:00 pm

1 stop8h 25m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, February is the cheapest month in which you can book a flight from Caribbean (average of $217). Flying from Caribbean in July will prove the most costly (average of $335). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Caribbean?

For flights departing from Caribbean check dates and pricing for the following: Frontier, JetBlue, Bahamasair, Southwest, American Airlines. These airlines depart to the following popular destinations: Orlando.

JetBlue
JetBlue
From $54
American Airlines
American Airlines
From $172
Copa Airlines
Copa Airlines
From $101
Frontier
Frontier
From $44

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 $27. Explore other affordable destinations below.

Port of Spain Piarco Intl
Port of Spain Piarco Intl
From $27
Scarborough ANR Robinson Intl
Scarborough ANR Robinson Intl
From $30
Nassau Intl
Nassau Intl
From $56
San Juan Luis Munoz Marin Intl
San Juan Luis Munoz Marin Intl
From $57

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 24 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.

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 July 25, 2026.

Those who are seeking the cheapest fare on flights departing from Caribbean would be wise to consider leaving during Tuesday at noon when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday at noon when fares are usually the most expensive.

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 August 1, 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,American Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Southwest
8.0
Very good
4,229 reviews
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
American Airlines
7.1
Good
11,850 reviews
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
JetBlue
7.1
Good
3,029 reviews
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Bahamasair
6.1
Okay
63 reviews
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.
Frontier
5.6
Fair
2,743 reviews
Southwest
8.0
Very good
4,229 reviews

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
6.0
Good

Scott,Feb 2026

HOU - FLL

Delayed by 45 minutes leaving Houston, making a 3.5 hour layover that much longer.

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 August 1, 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 $99; whereas Ponce Mercedita airport is typically cheaper if you're flying to Orlando, from $184. 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 July 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 Miami from $99 round trip
    Fly from San Juan to Fort Lauderdale from $99 round trip
    Fly from San Juan to Tampa from $162 round trip
    Fly from San Juan to Hartford from $175 round trip
    Fly from San Juan to Punta Cana from $176 round trip

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