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$1,023+ Cheap flights to Caribbean Islands

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
29 May — 5 Jun1
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
Explore the most affordable flight options available to Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on 29 April 2026.

Thu 28/517:50
SYD
-
SJU
2 stops43h 11m
American Airlines
Wed 3/615:39
SJU
-
SYD
2 stops49h 26m
American Airlines
Deal found 28/4$1,944
Sat 23/509:10
SYD
-
POS
2 stops43h 02m
American Airlines
Wed 27/507:00
POS
-
SYD
2 stops34h 05m
American Airlines
Deal found 24/4$2,054
Wed 18/1111:15
SYD
-
CUR
2 stops44h 25m
American Airlines
Sun 22/1117:40
CUR
-
SYD
2 stops48h 20m
American Airlines
Deal found 28/4$2,076
Thu 22/1010:30
SYD
-
SJU
2 stops43h 14m
United Airlines
Sun 22/1114:25
SJU
-
SYD
3 stops51h 50m
United Airlines
Deal found 24/4$2,077
Mon 21/913:15
SYD
-
CUR
3 stops37h 03m
Multiple Airlines
Sun 27/915:39
CUR
-
SYD
3 stops54h 11m
Multiple Airlines
Deal found 28/4$2,080
Fri 22/509:10
SYD
-
FPO
2 stops42h 02m
American Airlines
Mon 25/513:52
FPO
-
SYD
2 stops51h 13m
American Airlines
Deal found 24/4$2,126
Wed 6/509:15
SYD
-
SJU
2 stops28h 00m
Delta
Wed 13/507:30
SJU
-
SYD
2 stops33h 20m
Delta
Deal found 29/4$2,137
Tue 21/709:10
SYD
-
BGI
2 stops41h 52m
American Airlines
Fri 14/815:11
BGI
-
SYD
2 stops49h 54m
American Airlines
Deal found 25/4$2,140
Wed 9/909:10
SYD
-
BGI
2 stops42h 45m
American Airlines
Sun 13/915:45
BGI
-
SYD
2 stops49h 20m
American Airlines
Deal found 23/4$2,143
Sun 6/909:10
SYD
-
BGI
2 stops43h 23m
American Airlines
Thu 10/908:05
BGI
-
SYD
2 stops33h 00m
American Airlines
Deal found 26/4$2,144
Sun 18/1010:10
SYD
-
SDQ
2 stops39h 40m
American Airlines
Tue 20/1017:20
SDQ
-
SYD
2 stops47h 45m
American Airlines
Deal found 24/4$2,151
Tue 2/609:10
SYD
-
SDQ
2 stops51h 45m
American Airlines
Sat 6/607:00
SDQ
-
SYD
2 stops34h 05m
American Airlines
Deal found 23/4$2,154

Find flights to Caribbean Islands

Browse one-way and return flights deals to Caribbean Islands on Cheapflights. Flight deals are based on user searches and were last updated on 29 April 2026
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 Nassau
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

Find the latest flights to Caribbean Islands 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 29 April 2026.

Return from

$1,944

One-way from

$1,023

Popular in

March

Cheapest in

October

Average price

$2,299
American Airlines
  • American Airlines
  • 28/5-3/6
  • 4 total stops
  • 92h 37m total
  • Sydney to San Juan
Search Deals
American Airlines
  • American Airlines
  • 1/6
  • 2 total stops
  • 26h 49m total
  • Sydney to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($393 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($98 potential savings vs. average return price).
Search Deals
Average for return flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Locate flights to Caribbean Islands 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 29 April 2026.
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

SydneySan Juan

SYD - SJU

SYDSJU

Sydney Kingsford Smith

Thu 28/5

17:50-23:01

2 stops43h 11m

San Juan Luis Munoz Marin Intl

Wed 3/6

15:39-07:05

2 stops49h 26m

$1,944

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

15:12-07:05

2 stops49h 53m

$2,056

SydneySan Juan

SYD - SJU

SYDSJU

Sydney Kingsford Smith

Thu 22/10

10:30-14:44

2 stops43h 14m

San Juan Luis Munoz Marin Intl

Sun 22/11

14:25-09:15

3 stops51h 50m

$2,077

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Fri 22/5

09:10-13:12

2 stops42h 02m

Freeport Grand Bahama Intl

Mon 25/5

13:52-07:05

2 stops51h 13m

$2,126

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Sat 25/7

09:10-14:55

2 stops43h 45m

Bridgetown Grantley Adams Intl

Fri 14/8

08:00-07:05

2 stops33h 05m

$2,140

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Wed 22/7

09:10-14:55

2 stops43h 45m

Bridgetown Grantley Adams Intl

Fri 14/8

15:11-07:05

2 stops49h 54m

$2,140

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Fri 24/7

09:10-21:41

2 stops26h 31m

Bridgetown Grantley Adams Intl

Fri 14/8

15:11-07:05

2 stops49h 54m

$2,140

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Sun 18/10

10:10-10:50

2 stops39h 40m

Santo Domingo Las Americas

Tue 20/10

17:20-08:05

2 stops47h 45m

$2,151

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Tue 2/6

09:10-22:55

2 stops51h 45m

Santo Domingo Las Americas

Sat 6/6

07:00-07:05

2 stops34h 05m

$2,154

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Sun 3/5

09:10-21:16

2 stops26h 06m

Bridgetown Grantley Adams Intl

Wed 20/5

08:00-07:05

2 stops33h 05m

$2,161

Flights are sorted by cheapest return flights first.

Deals found on 28/4

Showing 1-10 of 34 resultsSorted by cheapest first
1
2
3
4

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
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 Islands

How long is the flight to Caribbean Islands?

On average, a flight from Sydney to Caribbean Islands takes 40 hours 21 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 $1,164
Air Canada
Air Canada
From $1,657
American Airlines
American Airlines
From $1,901
Qatar Airways
Qatar Airways
From $2,617

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

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

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

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated 29 April 2026.
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
9,680 reviews
Check prices

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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
9,680 reviews
United Airlines
7.4
Good
9,680 reviews
Check prices

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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
11,680 reviews
United Airlines
7.4
Good
9,680 reviews
Check prices

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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
10,979 reviews
United Airlines
7.4
Good
9,680 reviews
Check prices

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

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.

  • How much is a return flight to Caribbean Islands?

    A return flight to Caribbean Islands will typically cost around $260, however they can be found for as little as $260.

  • 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 (25 hours 4 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 Islands?

Deals for Caribbean Islands 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 Islands?

Millions of users choose and trust Cheapflights to book the best flight deals to Caribbean Islands for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights to Caribbean Islands with no change fees?

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.

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

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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