$1,110+ Cheap flights to Caribbean

— SJU
26 Oct — 2 Nov1
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

Mon 9/1109:15 -
2 stops30h 21m
Mon 16/1107:40 -
1 stop32h 20m
Deal found 24/9$1,700
Sat 24/1010:30 -
2 stops28h 20m
Sat 31/1016:50 -
2 stops49h 30m
Deal found 26/9$1,750
Sun 18/1013:00 -
1 stop25h 20m
Thu 29/1016:17 -
1 stop23h 38m
Deal found 23/9$2,049
Thu 5/1111:10 -
2 stops43h 27m
Mon 9/1116:42 -
2 stops49h 18m
Deal found 24/9$2,066
Wed 30/1211:20 -
2 stops42h 55m
Wed 27/116:43 -
2 stops49h 17m
Deal found 23/9$2,173
Wed 28/1011:10 -
2 stops40h 25m
Sun 1/1116:58 -
2 stops49h 02m
Deal found 24/9$2,180
Thu 5/1109:10 -
1 stop30h 08m
Sun 8/1101:25 -
2 stops40h 55m
Deal found 24/9$2,218
Fri 27/1109:15 -
1 stop22h 21m
Sun 20/1206:35 -
2 stops35h 30m
Deal found 24/9$2,370
Sun 27/1211:50 -
2 stops51h 28m
Sun 24/101:25 -
2 stops37h 55m
Deal found 23/9$2,380
Sat 24/1013:00 -
1 stop25h 20m
Sat 31/1006:00 -
1 stop33h 55m
Deal found 26/9$2,558
Fri 9/1010:10 -
2 stops25h 40m
Mon 12/1007:00 -
2 stops34h 05m
Deal found 25/9$2,832
Mon 26/1010:55 -
2 stops25h 27m
Fri 30/1013:21 -
2 stops28h 59m
Deal found 24/9$3,055

Find flight deals to Caribbean

One-way from

$1,110

Popular in

March

Cheapest in

January

Average price

$1,828
American Airlines
  • American Airlines
  • 13/10-31/12
  • 2 total stops
  • 38h 36m total
  • Sydney to Caribbean
Highest demand for flights based on searches. 17% potential increase in price ($490 potential increase over avg. return price).
Cheapest flight prices on average. 4% potential price decrease ($106 potential savings vs. average return price).
Average for return flights in September 2026

Cheapflights Fare Finder

 
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

SydneySan Juan

SYD Sydney Kingsford Smith - SJU San Juan Luis Munoz Marin Intl

SYDSJU

Sydney Kingsford Smith

Tue 13/10

10:10-09:46

2 stops38h 36m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-14:00

Nonstop0h 00m

$1,110

SydneySan Juan

SYD Sydney Kingsford Smith - SJU San Juan Luis Munoz Marin Intl

SYDSJU

Sydney Kingsford Smith

Tue 13/10

21:35-01:53

3 stops43h 18m

San Juan Luis Munoz Marin Intl

Wed 31/12

00:00-14:00

Nonstop0h 00m

$1,398

SydneySan Juan

SYD Sydney Kingsford Smith - SJU San Juan Luis Munoz Marin Intl

SYDSJU

Sydney Kingsford Smith

Sat 24/10

10:30-23:50

2 stops28h 20m

San Juan Luis Munoz Marin Intl

Sat 31/10

16:50-09:20

2 stops49h 30m

$1,750

SydneySan Juan

SYD Sydney Kingsford Smith - SJU San Juan Luis Munoz Marin Intl

SYDSJU

Sydney Kingsford Smith

Sun 18/10

13:00-23:20

1 stop25h 20m

San Juan Luis Munoz Marin Intl

Thu 29/10

12:21-09:00

2 stops29h 39m

$2,054

SydneyFreeport

SYD Sydney Kingsford Smith - FPO Freeport Grand Bahama Intl

SYDFPO

Sydney Kingsford Smith

Sat 27/2

11:20-12:12

2 stops64h 52m

Freeport Grand Bahama Intl

Wed 3/3

13:52-09:00

2 stops27h 08m

$2,141

SydneyPort of Spain

SYD Sydney Kingsford Smith - POS Port of Spain Piarco Intl

SYDPOS

Sydney Kingsford Smith

Wed 30/12

11:20-15:15

2 stops42h 55m

Port of Spain Piarco Intl

Wed 27/1

16:43-09:00

2 stops49h 17m

$2,173

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Wed 28/10

11:10-09:22

2 stops37h 12m

Santo Domingo Las Americas

Sun 1/11

15:53-09:00

2 stops50h 07m

$2,181

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Tue 2/3

11:20-10:02

2 stops37h 42m

Santo Domingo Las Americas

Wed 17/3

10:01-09:00

2 stops31h 59m

$2,210

SydneyPort of Spain

SYD Sydney Kingsford Smith - POS Port of Spain Piarco Intl

SYDPOS

Sydney Kingsford Smith

Thu 5/11

09:10-00:18

1 stop30h 08m

Port of Spain Piarco Intl

Sun 8/11

01:25-07:00

1 stop38h 35m

$2,218

SydneySan Juan

SYD Sydney Kingsford Smith - SJU San Juan Luis Munoz Marin Intl

SYDSJU

Sydney Kingsford Smith

Fri 27/11

09:15-16:36

1 stop22h 21m

San Juan Luis Munoz Marin Intl

Sun 20/12

06:35-09:05

2 stops35h 30m

$2,370

Flights are sorted by cheapest return flights first.

Deals found on 26/9

Showing 1-10 of 28 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

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 43 hours 16 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, American Airlines and Air Canada.

Rainfall in Caribbean 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

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?

The most popular places in Caribbean to fly to are Cuba, Jamaica, The Bahamas, Dominican Republic and Puerto Rico.

Reviews of airlines servicing Caribbean

See what other customers who have flown with United Airlines,Air Canada, andAmerican Airlines 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.

Comfort

7.3

Entertainment

7.1

Food

6.7

Boarding

7.7

Overall

7.4

Crew

8.1

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.

Comfort

7.3

Entertainment

7.1

Food

6.7

Boarding

7.7

Overall

7.4

Crew

8.1

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.

Comfort

7.3

Entertainment

7.1

Food

6.7

Boarding

7.7

Overall

7.4

Crew

8.1

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.

Comfort

7.3

Entertainment

7.1

Food

6.7

Boarding

7.7

Overall

7.4

Crew

8.1

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?

    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 $104, while return flights cost around $265.

  • 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 8 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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