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Caribbean

$79+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — MCO
Jul 15 — Jul 221
Wed 7/15
Wed 7/22
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 June 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

Sat 8/15

5:34 am-2:45 pm

1 stop10h 11m

Medellín Jose Maria Cordova Intl

Wed 8/19

9:15 am-4:14 pm

1 stop5h 59m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Fri 8/21

6:17 pm-10:55 am

1 stop17h 38m

Medellín Jose Maria Cordova Intl

Tue 8/25

9:15 am-4:14 pm

1 stop5h 59m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Tue 8/18

6:17 pm-2:15 pm

1 stop20h 58m

Medellín Jose Maria Cordova Intl

Thu 8/27

5:00 am-10:29 pm

1 stop16h 29m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 9/6

5:33 am-8:35 pm

1 stop16h 02m

Medellín Jose Maria Cordova Intl

Wed 9/9

5:00 am-4:14 pm

1 stop10h 14m

$195

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Thu 8/20

6:17 pm-2:15 pm

1 stop20h 58m

Medellín Jose Maria Cordova Intl

Mon 8/24

6:20 pm-4:14 pm

1 stop20h 54m

$205

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Fri 9/4

3:56 pm-8:05 pm

Nonstop5h 09m

Chicago O'Hare Intl

Tue 9/8

8:55 am-2:44 pm

Nonstop4h 49m

$227

San JuanChicago

SJU - ORD

SJUORD

San Juan Luis Munoz Marin Intl

Thu 8/13

4:55 pm-11:40 pm

1 stop7h 45m

Chicago O'Hare Intl

Tue 8/18

8:50 am-8:38 pm

1 stop10h 48m

$236

San JuanMedellín

SJU - MDE

SJUMDE

San Juan Luis Munoz Marin Intl

Sun 10/25

5:32 am-8:35 pm

1 stop16h 03m

Medellín Jose Maria Cordova Intl

Sat 10/31

9:15 am-4:14 pm

1 stop5h 59m

$256

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Fri 9/11

2:35 pm-10:05 pm

1 stop7h 30m

Miami

Sun 9/13

6:40 pm-12:30 am

1 stop5h 50m

$261

San JuanMiami

SJU - MIA

SJUMIA

San Juan Luis Munoz Marin Intl

Fri 9/11

2:35 pm-10:05 pm

1 stop7h 30m

Miami

Mon 9/14

6:20 am-2:30 pm

1 stop8h 10m

$266

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

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, February is the cheapest month in which you can book a flight from Caribbean (average of $217). Flying from Caribbean in June will prove the most costly (average of $321). 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 $165
Copa Airlines
Copa Airlines
From $101
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 $28. Explore other affordable destinations below.

Scarborough ANR Robinson Intl
Scarborough ANR Robinson Intl
From $28
Port of Spain Piarco Intl
Port of Spain Piarco Intl
From $30
Ceiba J. Aponte de la Torre
Ceiba J. Aponte de la Torre
From $57
Medellín Jose Maria Cordova Intl
Medellín Jose Maria Cordova Intl
From $64

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 62 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 June 13, 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 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 June 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,American Airlines, andJetBlue. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Southwest
7.9
Good
4,238 reviews
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
American Airlines
7.1
Good
11,662 reviews
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
JetBlue
7.1
Good
2,981 reviews
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Bahamasair
5.9
Fair
67 reviews
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.
Frontier
5.6
Fair
2,883 reviews
Southwest
7.9
Good
4,238 reviews

Food

7.0

Overall

7.9

Boarding

8.1

Crew

8.6

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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 June 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 $143; whereas Santo Domingo Las Americas airport is typically cheaper if you're flying to Atlanta, from $220. 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 June 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 $143 round trip
    Fly from San Juan to Fort Lauderdale from $158 round trip
    Fly from San Juan to Miami from $168 round trip
    Fly from San Juan to Orlando from $175 round trip
    Fly from San Juan to Chicago from $187 round trip

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