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$1,156+ 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 16/1. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
6 Feb — 13 Feb1
1 adult
1 adult, Economy, 0 bags

Flights to Caribbean in 2026

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 7 January 2026.

Return from

$2,517

One-way from

$1,156

Popular in

February

Cheapest in

October

Average price

$2,454
United Airlines
  • United Airlines
  • 19/2-26/2
  • 4 total stops
  • 61h 51m total
  • Sydney to San Juan
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16/1
  • 16/1
  • 2 total stops
  • 38h 30m total
  • Sydney to Caribbean
Search Deals
Highest demand for flights based on searches. 1% potential increase in price ($26 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease ($38 potential savings vs. average return price).
Search Deals
Average for return flights in January 2026
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Find flights to Caribbean

Browse one-way and return flights deals to Caribbean on Cheapflights. Flight deals are based on user searches and were last updated on 7 January 2026
Explore Caribbean
Look for other cheap flights to San Juan
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Look for other cheap flights to Port of Spain
Look for other cheap flights to Bridgetown
Look for other cheap flights to George Town
Look for other cheap flights to Willemstad

Find flight deals to Caribbean

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 7 January 2026.

Thu 19/311:20SYD - POS
2 stops41h 50mAmerican Airlines
Mon 23/315:10POS - SYD
2 stops50h 50mAmerican Airlines
Deal found 5/1$2,062
Thu 19/310:25SYD - POS
2 stops51h 58mUnited Airlines
Sun 22/300:30POS - SYD
1 stop39h 30mUnited Airlines
Deal found 5/1$2,074
Wed 18/211:20SYD - CUR
2 stops42h 43mAmerican Airlines
Sun 22/215:35CUR - SYD
2 stops50h 25mAmerican Airlines
Deal found 5/1$2,075
Thu 5/211:20SYD - SXM
2 stops40h 38mAmerican Airlines
Mon 9/216:24SXM - SYD
2 stops49h 36mAmerican Airlines
Deal found 5/1$2,115
Fri 6/211:20SYD - FPO
2 stops40h 36mAmerican Airlines
Fri 13/213:58FPO - SYD
2 stops27h 02mAmerican Airlines
Deal found 6/1$2,139
Thu 19/211:20SYD - FPO
2 stops41h 48mAmerican Airlines
Mon 23/213:58FPO - SYD
2 stops51h 02mAmerican Airlines
Deal found 5/1$2,140
Wed 18/211:20SYD - FPO
2 stops40h 17mAmerican Airlines
Wed 25/213:17FPO - SYD
2 stops27h 43mAmerican Airlines
Deal found 4/1$2,142
Thu 5/311:20SYD - BGI
2 stops43h 40mAmerican Airlines
Mon 9/307:15BGI - SYD
2 stops34h 45mAmerican Airlines
Deal found 5/1$2,155
Wed 18/211:20SYD - BGI
2 stops42h 30mAmerican Airlines
Wed 25/208:20BGI - SYD
2 stops33h 40mAmerican Airlines
Deal found 4/1$2,158
Sat 14/311:20SYD - PUJ
2 stops38h 33mAmerican Airlines
Tue 17/316:43PUJ - SYD
2 stops49h 17mAmerican Airlines
Deal found 5/1$2,166
Sat 24/111:20SYD - SDQ
2 stops40h 01mAmerican Airlines
Tue 27/106:00SDQ - SYD
2 stops36h 00mAmerican Airlines
Deal found 5/1$2,166
Sun 8/311:20SYD - SDQ
2 stops40h 40mAmerican Airlines
Wed 11/310:01SDQ - SYD
2 stops31h 59mAmerican Airlines
Deal found 4/1$2,167

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 7 January 2026.
Use the filters below to find and compare flights to Caribbean that are best for you.

Fly from

Sydney

Route

Depart

Return

Price

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Thu 19/3

11:20-14:10

2 stops41h 50m

Port of Spain Piarco Intl

Mon 23/3

15:10-09:00

2 stops50h 50m

$2,062

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Thu 19/3

11:50-23:23

1 stop26h 33m

Port of Spain Piarco Intl

Sun 22/3

00:30-07:00

1 stop39h 30m

$2,074

SydneyWillemstad

SYD - CUR

SYDCUR

Sydney Kingsford Smith

Wed 18/2

11:20-15:03

2 stops42h 43m

Willemstad Hato Int.

Sun 22/2

15:35-09:00

2 stops50h 25m

$2,075

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Fri 13/3

14:00-23:23

2 stops48h 23m

Port of Spain Piarco Intl

Sun 15/3

00:30-09:15

2 stops41h 45m

$2,075

SydneySimpson Bay

SYD - SXM

SYDSXM

Sydney Kingsford Smith

Thu 5/2

11:20-12:58

2 stops40h 38m

Simpson Bay Princess Juliana

Mon 9/2

16:24-09:00

2 stops49h 36m

$2,115

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Fri 6/2

11:20-11:56

2 stops40h 36m

Freeport Grand Bahama Intl

Fri 13/2

13:58-09:00

2 stops27h 02m

$2,139

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Thu 19/2

11:20-13:08

2 stops41h 48m

Freeport Grand Bahama Intl

Mon 23/2

13:58-09:00

2 stops51h 02m

$2,140

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Wed 18/2

11:20-11:37

2 stops40h 17m

Freeport Grand Bahama Intl

Wed 25/2

13:17-09:00

2 stops27h 43m

$2,142

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Thu 5/3

11:20-16:00

2 stops43h 40m

Bridgetown Grantley Adams Intl

Mon 9/3

07:15-09:00

2 stops34h 45m

$2,155

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Wed 18/2

11:20-14:50

2 stops42h 30m

Bridgetown Grantley Adams Intl

Wed 25/2

08:20-09:00

2 stops33h 40m

$2,158

Flights are sorted by cheapest return flights first.

Deals found on 6/1

Showing 1-10 of 38 results
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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 40 hours 47 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 most popular airlines that fly to Caribbean?

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

United Airlines
United Airlines
From $1,283
Qatar Airways
Qatar Airways
From $2,377
Air Canada
Air Canada
From $1,682
American Airlines
American Airlines
From $1,922

What are the cheapest airlines that fly to Caribbean?

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

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 7 January 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 7 January 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.
United Airlines
7.4
Good
9,138 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

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.
United Airlines
7.4
Good
9,138 reviews
United Airlines
7.4
Good
9,138 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

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.
American Airlines
7.2
Good
11,088 reviews
United Airlines
7.4
Good
9,138 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

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.
Air Canada
7.1
Good
10,599 reviews
United Airlines
7.4
Good
9,138 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

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.
British Airways
6.7
Okay
7,655 reviews
United Airlines
7.4
Good
9,138 reviews
Check prices

Comfort

7.3

Crew

8.1

Food

6.6

Boarding

7.7

Overall

7.4

Entertainment

7.1

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?

    Georgetown Exuma Intl is currently the cheapest airport to fly to in Caribbean. One-way flights to Georgetown Exuma Intl typically cost $120, while return flights cost around $221.

  • 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 (24 hours 36 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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