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$855+ 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 27/8. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
15 Jul — 22 Jul1
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 15 June 2026.

Mon 12/1018:50
SYD
-
KIN
2 stops37h 23m
American Airlines
Sun 1/1107:30
KIN
-
SYD
2 stops31h 25m
American Airlines
Deal found 12/6$1,573
Fri 14/809:10
SYD
-
SJU
2 stops42h 14m
American Airlines
Tue 18/815:44
SJU
-
SYD
2 stops25h 21m
American Airlines
Deal found 11/6$1,904
Mon 9/1114:00
SYD
-
CUR
3 stops61h 18m
Multiple Airlines
Sun 22/1119:21
CUR
-
SYD
3 stops50h 14m
Multiple Airlines
Deal found 15/6$1,911
Fri 14/809:30
SYD
-
SJU
2 stops25h 08m
United Airlines
Tue 18/807:00
SJU
-
SYD
2 stops33h 55m
United Airlines
Deal found 12/6$1,989
Fri 12/609:30
SYD
-
SJU
2 stops28h 20m
United Airlines
Thu 18/607:20
SJU
-
SYD
2 stops33h 40m
United Airlines
Deal found 11/6$2,030
Wed 21/1010:10
SYD
-
POS
2 stops42h 50m
American Airlines
Fri 6/1116:28
POS
-
SYD
2 stops49h 32m
American Airlines
Deal found 13/6$2,058
Mon 3/809:10
SYD
-
POS
2 stops27h 23m
American Airlines
Mon 31/807:00
POS
-
SYD
2 stops34h 05m
American Airlines
Deal found 15/6$2,066
Thu 29/1011:15
SYD
-
FPO
2 stops62h 54m
American Airlines
Sun 1/1114:19
FPO
-
SYD
2 stops50h 41m
American Airlines
Deal found 10/6$2,123
Sun 14/609:10
SYD
-
FPO
2 stops40h 03m
American Airlines
Sat 4/713:53
FPO
-
SYD
2 stops27h 12m
American Airlines
Deal found 13/6$2,133
Thu 30/709:10
SYD
-
FPO
2 stops39h 59m
American Airlines
Thu 6/811:42
FPO
-
SYD
2 stops29h 23m
American Airlines
Deal found 15/6$2,136
Sat 10/1010:10
SYD
-
PUJ
2 stops41h 25m
American Airlines
Tue 17/1112:55
PUJ
-
SYD
2 stops29h 05m
American Airlines
Deal found 14/6$2,160
Mon 13/709:10
SYD
-
CUR
2 stops42h 37m
American Airlines
Mon 20/716:40
CUR
-
SYD
2 stops48h 25m
American Airlines
Deal found 15/6$2,165

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 15 June 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 Providenciales
Look for other cheap flights to Port of Spain
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 15 June 2026.

Return from

$1,904

One-way from

$855

Popular in

March

Cheapest in

October

Average price

$2,097
American Airlines
  • American Airlines
  • 14/8-18/8
  • 4 total stops
  • 67h 35m total
  • Sydney to San Juan
Search Deals
Delta
  • Delta
  • 27/8
  • 2 total stops
  • 27h 14m total
  • Sydney to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($538 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($100 potential savings vs. average return price).
Search Deals
Average for return flights in June 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 15 June 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

Fri 14/8

09:10-13:24

2 stops42h 14m

San Juan Luis Munoz Marin Intl

Tue 18/8

15:44-07:05

2 stops25h 21m

$1,904

SydneySan Juan

SYD - SJU

SYDSJU

Sydney Kingsford Smith

Fri 14/8

09:30-20:38

2 stops25h 08m

San Juan Luis Munoz Marin Intl

Tue 18/8

07:00-06:55

2 stops33h 55m

$1,989

SydneyWillemstad

SYD - CUR

SYDCUR

Sydney Kingsford Smith

Mon 9/11

11:15-14:37

2 stops42h 22m

Willemstad Hato Int.

Sun 22/11

19:21-09:00

2 stops46h 39m

$2,035

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Thu 29/10

11:15-11:09

2 stops62h 54m

Freeport Grand Bahama Intl

Sun 1/11

14:19-09:00

2 stops50h 41m

$2,123

SydneyFreeport

SYD - FPO

SYDFPO

Sydney Kingsford Smith

Thu 30/7

09:10-11:09

2 stops39h 59m

Freeport Grand Bahama Intl

Thu 6/8

11:42-07:05

2 stops29h 23m

$2,136

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Tue 13/10

10:10-13:35

2 stops42h 25m

Punta Cana

Thu 19/11

15:54-10:55

2 stops28h 01m

$2,196

SydneyPort of Spain

SYD - POS

SYDPOS

Sydney Kingsford Smith

Wed 21/10

11:20-23:23

2 stops51h 03m

Port of Spain Piarco Intl

Thu 5/11

01:30-07:00

1 stop38h 30m

$2,208
Fastest return journey

SydneyKingston

SYD - KIN

SYDKIN

Sydney Kingsford Smith

Fri 31/7

09:10-20:12

2 stops26h 02m

Kingston Norman Manley

Fri 7/8

14:00-07:05

2 stops26h 05m

$2,242

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Sat 10/10

10:30-15:30

2 stops44h 00m

Punta Cana

Sat 21/11

15:28-07:00

1 stop24h 32m

$2,311

SydneyPunta Cana

SYD - PUJ

SYDPUJ

Sydney Kingsford Smith

Tue 13/10

10:30-12:40

2 stops41h 10m

Punta Cana

Sat 21/11

15:28-07:00

1 stop24h 32m

$2,311

Flights are sorted by cheapest return flights first.

Deals found on 13/6

Showing 1-10 of 31 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
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 35 hours 11 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 $1,180
American Airlines
American Airlines
From $1,928
Qatar Airways
Qatar Airways
From $2,715
Air Canada
Air Canada
From $2,143

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 15 June 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
9,830 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,830 reviews
United Airlines
7.4
Good
9,830 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
American Airlines
7.1
Good
11,660 reviews
United Airlines
7.4
Good
9,830 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
11,194 reviews
United Airlines
7.4
Good
9,830 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

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

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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.

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