$1,030+ Cheap flights to 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 1/6. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
23 May — 30 May1
1 adult
1 adult, Economy, 0 bags

Flights to Caribbean in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Caribbean
Explore the most affordable flight options available to Caribbean. Find the lowest fares based on data from user searches, with prices last updated on 23 April 2026.

Thu 21/509:10
SYD
-
SJU
2 stops26h 49m
American Airlines
Thu 28/510:29
SJU
-
SYD
2 stops30h 36m
American Airlines
Deal found 23/4$1,959
Sat 23/509:10
SYD
-
POS
2 stops43h 02m
American Airlines
Wed 27/507:00
POS
-
SYD
2 stops34h 05m
American Airlines
Deal found 22/4$2,068
Sun 8/1111:15
SYD
-
CUR
2 stops42h 10m
American Airlines
Wed 11/1115:26
CUR
-
SYD
2 stops50h 34m
American Airlines
Deal found 21/4$2,081
Sun 8/1111:15
SYD
-
SXM
2 stops42h 02m
American Airlines
Wed 11/1117:24
SXM
-
SYD
2 stops48h 36m
American Airlines
Deal found 20/4$2,119
Sun 31/509:10
SYD
-
SXM
2 stops42h 12m
American Airlines
Wed 3/616:43
SXM
-
SYD
2 stops48h 22m
American Airlines
Deal found 18/4$2,121
Fri 22/509:10
SYD
-
FPO
2 stops40h 18m
American Airlines
Mon 25/513:52
FPO
-
SYD
2 stops51h 13m
American Airlines
Deal found 20/4$2,142
Sun 17/509:10
SYD
-
FPO
2 stops62h 32m
American Airlines
Thu 21/511:53
FPO
-
SYD
2 stops29h 12m
American Airlines
Deal found 18/4$2,145
Wed 9/909:10
SYD
-
BGI
2 stops50h 10m
American Airlines
Sun 13/908:05
BGI
-
SYD
2 stops57h 00m
American Airlines
Deal found 21/4$2,156
Sun 3/509:10
SYD
-
PUJ
2 stops41h 52m
American Airlines
Thu 28/513:53
PUJ
-
SYD
2 stops27h 12m
American Airlines
Deal found 21/4$2,168
Tue 2/609:10
SYD
-
SDQ
2 stops42h 05m
American Airlines
Sat 6/607:00
SDQ
-
SYD
2 stops34h 05m
American Airlines
Deal found 20/4$2,168
Sun 31/509:10
SYD
-
PUJ
2 stops41h 42m
American Airlines
Wed 3/617:48
PUJ
-
SYD
2 stops47h 17m
American Airlines
Deal found 19/4$2,169
Sun 17/509:10
SYD
-
SDQ
2 stops51h 45m
American Airlines
Thu 21/510:25
SDQ
-
SYD
2 stops54h 40m
American Airlines
Deal found 18/4$2,170

Find flight deals to Caribbean

Find the latest flights to Caribbean in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 23 April 2026.

Return from

$2,158

One-way from

$1,030

Popular in

March

Cheapest in

October

Average price

$2,309
United Airlines
  • United Airlines
  • 2/6-9/6
  • 4 total stops
  • 74h 23m total
  • Sydney to San Juan
American Airlines
  • American Airlines
  • 1/6
  • 2 total stops
  • 28h 29m total
  • Sydney to Caribbean
Highest demand for flights based on searches. 16% potential increase in price ($395 potential increase over avg. return price).
Cheapest flight prices on average. 4% potential price decrease ($98 potential savings vs. average return price).
Average for return flights in April 2026

Cheapflights Fare Finder

 
Locate flights to Caribbean that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 647,157 searches and data was last updated on 23 April 2026.
Use the filters below to find and compare flights to Caribbean that are best for you.

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Sat 23/5

09:10-14:12

2 stops43h 02m

Port of Spain Piarco Intl

Wed 27/5

07:00-07:05

2 stops34h 05m

$2,068

SydneySimpson Bay

SYD - SXM

SYDSXM

Sydney Kingsford Smith

Sun 31/5

09:10-13:22

2 stops42h 12m

Simpson Bay Princess Juliana

Wed 3/6

16:43-07:05

2 stops48h 22m

$2,121

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Fri 22/5

09:10-11:28

2 stops40h 18m

Freeport Grand Bahama Intl

Mon 25/5

13:52-07:05

2 stops51h 13m

$2,142

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Sun 17/5

09:10-09:42

2 stops62h 32m

Freeport Grand Bahama Intl

Thu 21/5

11:53-07:05

2 stops29h 12m

$2,145

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Wed 9/9

09:10-13:55

2 stops42h 45m

Bridgetown Grantley Adams Intl

Sun 13/9

15:45-07:05

2 stops49h 20m

$2,156

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Sun 31/5

09:10-16:48

2 stops45h 38m

Punta Cana

Wed 3/6

11:50-07:05

2 stops29h 15m

$2,168

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Wed 6/5

09:10-13:02

2 stops41h 52m

Punta Cana

Mon 1/6

13:53-07:05

2 stops27h 12m

$2,168

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Tue 2/6

09:10-13:15

2 stops42h 05m

Santo Domingo Las Americas

Sat 6/6

07:00-07:05

2 stops34h 05m

$2,168

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Sun 17/5

09:10-22:55

2 stops51h 45m

Santo Domingo Las Americas

Thu 21/5

10:25-07:05

2 stops54h 40m

$2,170

SydneyKingston

SYD - KIN

SYDKIN

Sydney Kingsford Smith

Sun 7/6

09:10-11:41

2 stops41h 31m

Kingston Norman Manley

Wed 10/6

17:06-07:05

2 stops46h 59m

$2,243

Flights are sorted by cheapest return flights first.

Deals found on 23/4

Showing 1-10 of 34 resultsSorted by cheapest first
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Best time to book a flight to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean with our price prediction graph.
Estimated return 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.

Cheapflights Insights

Everything you need to know about your flight to Caribbean

How long is the flight to Caribbean?

On average, a flight from Sydney to Caribbean takes 37 hours 25 minutes. Flights to Caribbean from other popular cities in Australia will vary in length. Below are a few examples of popular routes and their flight times.

What are the cheapest airlines that fly to Caribbean?

The cheapest airlines flying from Sydney to Caribbean are United Airlines, Air Canada and American Airlines.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 55.0 - 156.0 mm per month. November is typically the wettest month, when rainfall can reach 156.0 mm. March is typically the driest time to visit Caribbean when rainfall is around 55.0 mm.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 28.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 25.0 C).

What are the most popular places to fly to in Caribbean?

Destination popularity is based on the amount of flight searches to Caribbean in the last few years. This data was updated on 23 April 2026.
The most popular places in Caribbean to fly to are Cuba, Jamaica, The Bahamas, Dominican Republic and Puerto Rico.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated 23 April 2026.
See what other customers who have flown with United Airlines,American Airlines, andAir Canada to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

Boarding

7.7

Overall

7.4

Crew

8.1

Food

6.6

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

FAQs about flying to Caribbean

  • What is the best way to travel around the Caribbean?

    If you book flights to the Caribbean and secure a Caribbean airfare, you may want to find the best way to travel in-between the islands. Air travel is relatively inexpensive, and Caribbean flight deals offer several routes which are mainly served by Seaborn, Caribbean and Sunrise airlines. Cheap flights to Caribbean islands exist between popular destinations such as Cuba, Barbados, Jamaica, Grenada and The Bahamas, which can prove useful if fair distances are involved. Another option would be to book a cruise which will transport you between some of the larger and most visited islands which can be convenient and you will find several operators offering this service at varying prices.

  • What are some things to do in the Caribbean?

    The Caribbean has a wealth of options to explore. If you are visiting the Dominican Republic, make sure to visit the Punta Cana resort which boasts emerald waters and some of the best white sandy beaches on the island. Costa Rica is a nature lovers paradise and is well renowned for its spectacular national parks and rainforests where you can experience a wide range of exotic wildlife. Puerto Rico is equally known for its beautiful beaches and national parks and boasts a unique Spanish Caribbean culture with American influences which is reflected in the local cuisine.

  • How long is the flight to the Caribbean?

    If you are flying to the Caribbean, you can find flights to the Caribbean from Sydney Kingsford Smith Airport (SYD) in Australia to San Juan Luis Munoz Marin International Airport in Puerto Rico with flight times averaging between 45 and 54h, including two stopovers in Abu Dhabi Airport (AUH) and New York (JFK) Airport. You can also book flights to the Caribbean from Brisbane Airport (BNE) to San Jose Juan Santamaria International Airport (SJO) in Costa Rica around 35h with one stopover in Los Angeles Airport (LAX). You can also compare flights to the Caribbean and find Caribbean flight deals to Costa Rica from Melbourne Airport (MEL) to San Jose Airport with flight times under 24h and one stopover in Los Angeles Airport. Equally, you can find cheap flights to the Caribbean from Melbourne Airport to Santo Domingo Las Americas Airport (SDQ) in Dominican Republic with flight times just under 39h and two stopovers in Dubai (DXB) and New York (JFK) airports.

  • What do I need to do before my flight to the Caribbean?

    If you have flights to the Caribbean booked, you will be pleased to know that many Caribbean Islands are visa free for Australian citizens, including The Bahamas, Barbados, Costa Rica, Dominican Republic and Puerto Rico who all guarantee stays of up to 90 days, with Puerto Rico requiring an ESTA travel authorisation which can be obtained online. You will need a valid passport to travel, however, and it may also be beneficial to check your mobile network compatibility for the Caribbean region. You could take advantage of price plans offered by T-Mobile who have an international option available which has coverage throughout the Caribbean region.

  • Can I find cheaper flights to Caribbean if I am willing to have stopovers?

    Yes, flights with stopovers are often cheaper than direct flights. Keep an eye out for flight deals to Caribbean on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Caribbean?

    Based on reviews from Cheapflights users, United Airlines is rated the highest out of the airlines that fly to Caribbean.

  • What is the cheapest airport to fly to in Caribbean?

    San Juan Luis Munoz Marin Intl is currently the cheapest airport to fly to in Caribbean. One-way flights to San Juan Luis Munoz Marin Intl typically cost $157, while return flights cost around $261.

  • How much is a return flight to Caribbean?

    A return flight to Caribbean will typically cost around $261, however they can be found for as little as $261.

  • Where does the fastest flight to Caribbean depart from?

    For those looking to save time traveling to Caribbean, Sydney Kingsford Smith offers the quickest one-way flight (25 hours 45 minutes).

  • Does San Juan Luis Munoz Marin Intl have car hire?

    Yes. Those touching down at San Juan Luis Munoz Marin Intl can take advantage of the car hire services offered upon their arrival.

  • Are there hotels close to San Juan Luis Munoz Marin Intl?

    Yes. San Juan Luis Munoz Marin Intl has hotels nearby for those requiring accommodations. San Juan Airport Hotel is the closest property to San Juan Luis Munoz Marin Intl (0.0 km away from San Juan Luis Munoz Marin Intl).

See more FAQs

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How does Cheapflights help users find flights to Caribbean?

Deals for Caribbean flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose to your preference, such as price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets to Caribbean?

Cheapflights helps you find that perfect flight to Caribbean by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights to Caribbean with no change fees?

Users can book flights with no change fees policies with our dedicated filters. Book flights to Caribbean flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights to Caribbean become cheaper?

Yes, Cheapflights offers price alerts on Caribbean flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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