Find flights
Airlines

$1,028+ 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 31/1. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
27 Feb — 6 Mar1
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 28 January 2026.

Mon 2/317:45
SYD
-
SJU
2 stops31h 15m
American Airlines
Sun 8/315:01
SJU
-
SYD
2 stops51h 44m
American Airlines
Deal found 27/1$1,649
Mon 2/311:50
SYD
-
SJU
1 stop24h 36m
United Airlines
Sun 8/316:50
SJU
-
SYD
2 stops49h 25m
United Airlines
Deal found 27/1$1,901
Thu 19/312:10
SYD
-
POS
2 stops50h 13m
United Airlines
Sun 22/300:30
POS
-
SYD
1 stop39h 30m
United Airlines
Deal found 25/1$2,068
Wed 18/211:20
SYD
-
CUR
2 stops42h 15m
American Airlines
Sun 22/217:42
CUR
-
SYD
2 stops48h 18m
American Airlines
Deal found 25/1$2,070
Thu 5/211:20
SYD
-
SXM
2 stops41h 22m
American Airlines
Mon 9/217:33
SXM
-
SYD
2 stops48h 27m
American Airlines
Deal found 25/1$2,109
Thu 19/211:20
SYD
-
FPO
2 stops41h 48m
American Airlines
Mon 23/212:17
FPO
-
SYD
2 stops28h 43m
American Airlines
Deal found 25/1$2,135
Wed 4/311:20
SYD
-
BGI
2 stops42h 30m
American Airlines
Sun 8/307:15
BGI
-
SYD
2 stops34h 45m
American Airlines
Deal found 25/1$2,149
Fri 13/311:20
SYD
-
SDQ
2 stops26h 33m
American Airlines
Fri 20/314:16
SDQ
-
SYD
2 stops27h 44m
American Airlines
Deal found 26/1$2,150
Sat 14/311:20
SYD
-
PUJ
2 stops38h 33m
American Airlines
Tue 17/311:53
PUJ
-
SYD
2 stops30h 07m
American Airlines
Deal found 25/1$2,158
Fri 24/409:10
SYD
-
SDQ
2 stops42h 08m
American Airlines
Tue 28/417:55
SDQ
-
SYD
2 stops47h 10m
American Airlines
Deal found 25/1$2,158
Wed 4/1107:00
SYD
-
PUJ
2 stops24h 52m
American Airlines
Mon 9/1112:46
PUJ
-
SYD
2 stops29h 14m
American Airlines
Deal found 27/1$2,219
Tue 26/509:10
SYD
-
KIN
2 stops45h 57m
American Airlines
Thu 28/506:25
KIN
-
SYD
2 stops33h 40m
American Airlines
Deal found 26/1$2,241

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 28 January 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 Saint Thomas Island
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 28 January 2026.

Return from

$1,649

One-way from

$1,028

Popular in

February

Cheapest in

March

Average price

$2,376
American Airlines
  • American Airlines
  • 2/3-8/3
  • 4 total stops
  • 82h 59m total
  • Sydney to San Juan
Search Deals
31/1
  • 31/1
  • 3 total stops
  • 45h 00m total
  • Sydney to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($9 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($35 potential savings vs. average return price).
Search Deals
Average for return flights in January 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 28 January 2026.
Use the filters below to find and compare flights to Caribbean Islands that are best for you.

Fly from

Sydney

Route

Depart

Return

Price

SydneySan Juan

SYD - SJU

SYDSJU

Sydney Kingsford Smith

Mon 2/3

17:45-10:00

2 stops31h 15m

San Juan Luis Munoz Marin Intl

Sun 8/3

15:01-09:45

2 stops51h 44m

$1,649

SydneySan Juan

SYD - SJU

SYDSJU

Sydney Kingsford Smith

Mon 2/3

11:50-21:26

1 stop24h 36m

San Juan Luis Munoz Marin Intl

Sun 8/3

16:50-09:15

2 stops49h 25m

$1,901

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Thu 19/3

12:10-23:23

2 stops50h 13m

Port of Spain Piarco Intl

Sun 22/3

00:30-09:05

2 stops41h 35m

$2,068

SydneyWillemstad

SYD - CUR

SYDCUR

Sydney Kingsford Smith

Wed 18/2

11:20-14:35

2 stops42h 15m

Willemstad Hato Int.

Sun 22/2

17:42-09:00

2 stops48h 18m

$2,070

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Thu 19/2

11:20-13:08

2 stops41h 48m

Freeport Grand Bahama Intl

Mon 23/2

12:17-09:00

2 stops28h 43m

$2,135

SydneyBridgetown

SYD - BGI

SYDBGI

Sydney Kingsford Smith

Wed 4/3

11:20-14:50

2 stops42h 30m

Bridgetown Grantley Adams Intl

Sun 8/3

07:15-09:00

2 stops34h 45m

$2,149

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Fri 13/3

11:20-22:53

2 stops26h 33m

Santo Domingo Las Americas

Fri 20/3

14:16-09:00

2 stops27h 44m

$2,150

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Sat 14/3

11:20-10:53

2 stops38h 33m

Punta Cana

Tue 17/3

11:53-09:00

2 stops30h 07m

$2,158

SydneySanto Domingo

SYD - SDQ

SYDSDQ

Sydney Kingsford Smith

Fri 24/4

09:10-13:18

2 stops42h 08m

Santo Domingo Las Americas

Tue 28/4

10:20-07:05

2 stops30h 45m

$2,158

SydneyKingston

SYD - KIN

SYDKIN

Sydney Kingsford Smith

Tue 26/5

09:10-16:07

2 stops45h 57m

Kingston Norman Manley

Thu 28/5

06:25-07:05

2 stops33h 40m

$2,241

Flights are sorted by cheapest return flights first.

Deals found on 27/1

Showing 1-10 of 35 results
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 47 hours 38 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, Air Canada and American Airlines.

United Airlines
United Airlines
From $1,202
Qatar Airways
Qatar Airways
From $2,301
Air Canada
Air Canada
From $1,628
American Airlines
American Airlines
From $1,861

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 28 January 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
9,209 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

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
9,209 reviews
United Airlines
7.4
Good
9,209 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

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
11,201 reviews
United Airlines
7.4
Good
9,209 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

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
10,666 reviews
United Airlines
7.4
Good
9,209 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

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
7,704 reviews
United Airlines
7.4
Good
9,209 reviews
Check prices

Comfort

7.3

Boarding

7.7

Food

6.6

Entertainment

7.1

Crew

8.1

Overall

7.4

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 (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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Search flights to Caribbean Islands by cabin class

Find flights to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
First Class
Business Class
Premium Economy Class
Economy class

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.