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$921+ Cheap flights to Caribbean Islands

— SJU
3 Oct — 10 Oct1
1 adult
1 adult, Economy, 0 bags

Flights to Caribbean Islands in 2026

Enter your travel dates to find the best prices.

Cheapest flights to Caribbean Islands

Wed 14/1010:10 -
2 stops38h 36m
Fri 23/1006:30 -
2 stops34h 35m
Deal found 1/9$1,724
Thu 15/1010:10 -
2 stops28h 10m
Thu 22/1010:36 -
2 stops30h 29m
Deal found 31/8$1,750
Thu 15/1010:30 -
2 stops25h 08m
Thu 22/1018:45 -
2 stops46h 10m
Deal found 30/8$1,752
Thu 5/1111:10 -
2 stops43h 27m
Mon 9/1116:42 -
2 stops49h 18m
Deal found 2/9$2,065
Sun 25/1010:10 -
2 stops42h 13m
Thu 29/1016:39 -
2 stops49h 21m
Deal found 1/9$2,114
Thu 12/1116:20 -
3 stops46h 06m
Fri 20/1116:23 -
3 stops46h 32m
Deal found 29/8$2,118
Thu 22/1010:10 -
2 stops38h 12m
Mon 26/1016:20 -
2 stops49h 40m
Deal found 2/9$2,177
Wed 9/909:10 -
2 stops38h 11m
Wed 16/909:30 -
2 stops31h 35m
Deal found 1/9$2,181
Thu 5/1109:20 -
1 stop29h 58m
Sun 8/1101:25 -
2 stops40h 55m
Deal found 2/9$2,216
Thu 12/1111:10 -
2 stops27h 16m
Fri 20/1107:00 -
2 stops34h 00m
Deal found 29/8$2,241
Fri 16/1010:10 -
2 stops39h 29m
Fri 23/1011:39 -
2 stops29h 26m
Deal found 31/8$2,273
Sun 27/909:10 -
2 stops41h 54m
Wed 30/917:08 -
2 stops46h 57m
Deal found 2/9$2,333

Find flights to Caribbean Islands

Explore Caribbean Islands
Look for other cheap flights to San Juan
Look for other cheap flights to Punta Cana
Look for other cheap flights to Santo Domingo
Look for other cheap flights to Montego Bay
Look for other cheap flights to Oranjestad
Look for other cheap flights to Kingston
Look for other cheap flights to Simpson Bay
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 Islands

Return from

$1,724

One-way from

$1,430

Popular in

March

Cheapest in

January

Average price

$1,795
American Airlines
  • American Airlines
  • 14/10-23/10
  • 4 total stops
  • 73h 11m total
  • Sydney to San Juan
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23/10-31/12
  • 23/10-31/12
  • 2 total stops
  • 59h 34m total
  • Sydney to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($480 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($104 potential savings vs. average return price).
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Average for return flights in September 2026
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Cheapflights Fare Finder

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

Fly from

Route

Depart

Return

Price

Cheapest return flight

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Sat 16/1

12:00-20:35

2 stops47h 35m

Santo Domingo Las Americas

Wed 31/12

00:00-14:30

Nonstop0h 00m

$1,233
Fastest return journey

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Mon 18/1

22:20-05:25

2 stops46h 05m

Santo Domingo Las Americas

Wed 31/12

00:00-14:30

Nonstop0h 00m

$1,320

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Fri 15/1

12:00-19:35

2 stops46h 35m

Santo Domingo Las Americas

Wed 31/12

00:00-14:30

Nonstop0h 00m

$1,413

SydneySimpson Bay

SYD Sydney Kingsford Smith - SXM Simpson Bay Princess Juliana

SYDSXM

Sydney Kingsford Smith

Fri 23/10

15:05-11:39

2 stops59h 34m

Simpson Bay Princess Juliana

Wed 31/12

00:00-14:00

Nonstop0h 00m

$1,430

SydneyPunta Cana

SYD Sydney Kingsford Smith - PUJ Punta Cana

SYDPUJ

Sydney Kingsford Smith

Mon 9/11

11:20-23:35

2 stops51h 15m

Punta Cana

Wed 31/12

00:00-14:30

Nonstop0h 00m

$1,731

SydneySan Juan

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

SYDSJU

Sydney Kingsford Smith

Thu 15/10

10:30-20:38

2 stops25h 08m

San Juan Luis Munoz Marin Intl

Thu 22/10

18:45-07:55

2 stops46h 10m

$1,752

SydneyWillemstad

SYD Sydney Kingsford Smith - CUR Willemstad Hato Int.

SYDCUR

Sydney Kingsford Smith

Sun 28/2

11:20-16:41

2 stops44h 21m

Willemstad Hato Int.

Wed 3/3

16:05-09:00

2 stops49h 55m

$2,076

SydneySimpson Bay

SYD Sydney Kingsford Smith - SXM Simpson Bay Princess Juliana

SYDSXM

Sydney Kingsford Smith

Sun 25/10

10:10-13:23

2 stops42h 13m

Simpson Bay Princess Juliana

Thu 29/10

16:39-09:00

2 stops49h 21m

$2,114

SydneyKingston

SYD Sydney Kingsford Smith - KIN Kingston Norman Manley

SYDKIN

Sydney Kingsford Smith

Thu 12/11

16:20-22:26

3 stops46h 06m

Kingston Norman Manley

Fri 20/11

16:23-06:55

3 stops46h 32m

$2,118

SydneyFreeport

SYD Sydney Kingsford Smith - FPO Freeport Grand Bahama Intl

SYDFPO

Sydney Kingsford Smith

Sat 27/2

11:20-13:02

2 stops41h 42m

Freeport Grand Bahama Intl

Wed 3/3

12:52-09:00

2 stops52h 08m

$2,139

Flights are sorted by cheapest return flights first.

Deals found on 3/9

Showing 1-10 of 35 resultsSorted by cheapest first
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Best time to book a flight to Caribbean Islands

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

Cheapflights Insights

Everything you need to know about your flight to Caribbean Islands

How long is the flight to Caribbean Islands?

On average, a flight from Sydney to Caribbean Islands takes 43 hours 53 minutes. Flights to Caribbean Islands 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 Islands?

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

United Airlines
United Airlines
From $1,617
American Airlines
American Airlines
From $1,994
Air Canada
Air Canada
From $3,540
British Airways
British Airways
From $2,448

What are the cheapest airlines that fly to Caribbean Islands?

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

Rainfall in Caribbean Islands by month

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 55.0 mm.

Temperature in Caribbean Islands by month

If weather is an important factor for your trip to Caribbean Islands, 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).

Reviews of airlines servicing Caribbean Islands

Read through reviews of airlines serving Caribbean Islands, such as United Airlines,American Airlines, andAir Canada. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
10,160 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.7

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
10,160 reviews
United Airlines
7.4
Good
10,160 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.7

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
7.1
Good
12,030 reviews
United Airlines
7.4
Good
10,160 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.7

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
11,573 reviews
United Airlines
7.4
Good
10,160 reviews
Check prices

Comfort

7.3

Overall

7.4

Boarding

7.7

Crew

8.1

Entertainment

7.1

Food

6.7

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 Islands

  • Can I find cheaper flights to Caribbean Islands 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 Islands on Cheapflights that require 1 or 2 stops for potential cost savings.

  • What is the best airline to fly to Caribbean Islands?

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

  • Where does the fastest flight to Caribbean Islands depart from?

    For those looking to save time traveling to Caribbean Islands, Sydney Kingsford Smith offers the quickest one-way flight (26 hours 26 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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Need flexible booking options for your flight to Caribbean Islands ? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

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Of course! You can track prices for flights to Caribbean Islands and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals to set up your price alerts.

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