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$1,670+ Cheap flights to Caribbean

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 20/9. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
5 Sep — 12 Sep1
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
Explore the most affordable flight options available to Caribbean. Find the lowest fares based on data from user searches, with prices last updated on 6 August 2026.

Thu 6/809:10 -
2 stops43h 44m
Mon 10/819:24 -
2 stops45h 41m
Deal found 3/8$1,713
Wed 16/909:10 -
2 stops25h 37m
Wed 23/911:51 -
2 stops29h 14m
Deal found 2/8$1,720
Sun 15/1111:20 -
2 stops25h 09m
Thu 3/1214:50 -
2 stops27h 10m
Deal found 5/8$1,818
Thu 5/1111:20 -
2 stops26h 12m
Mon 30/1106:28 -
1 stop33h 27m
Deal found 2/8$1,841
Mon 26/1010:20 -
2 stops67h 25m
Fri 30/1015:45 -
2 stops49h 50m
Deal found 3/8$1,916
Sun 15/1109:15 -
1 stop22h 21m
Thu 3/1215:46 -
1 stop24h 14m
Deal found 5/8$1,920
Tue 27/1010:20 -
2 stops42h 05m
Fri 30/1015:00 -
2 stops50h 35m
Deal found 3/8$1,971
Wed 28/1010:20 -
2 stops42h 30m
Sun 1/1115:45 -
2 stops50h 50m
Deal found 3/8$2,032
Wed 11/1111:20 -
2 stops43h 17m
Sat 14/1116:42 -
2 stops49h 18m
Deal found 3/8$2,058
Mon 26/1011:10 -
2 stops65h 13m
Fri 30/1016:39 -
2 stops49h 21m
Deal found 4/8$2,115
Thu 3/909:10 -
2 stops38h 15m
Thu 10/910:21 -
2 stops54h 44m
Deal found 4/8$2,115
Tue 27/1011:10 -
2 stops49h 49m
Fri 30/1015:52 -
2 stops50h 08m
Deal found 4/8$2,153

Find flights to Caribbean

Browse one-way and return flights deals to Caribbean on Cheapflights. Flight deals are based on user searches and were last updated on 6 August 2026
Explore Caribbean
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

Find flight deals to Caribbean

Find the latest flights to Caribbean 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 6 August 2026.

Return from

$1,720

One-way from

$1,670
American Airlines
  • American Airlines
  • 16/9-23/9
  • 4 total stops
  • 54h 51m total
  • Sydney to San Juan
Search Deals
20/9
  • 20/9
  • 3 total stops
  • 47h 00m total
  • Sydney to Caribbean
Search Deals

Cheapflights Fare Finder

 
Locate flights to Caribbean 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 6 August 2026.
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

Thu 5/11

11:20-00:16

2 stops27h 56m

San Juan Luis Munoz Marin Intl

Mon 30/11

08:25-06:55

2 stops31h 30m

$1,841

SydneySimpson Bay

SYD Sydney Kingsford Smith - SXM Simpson Bay Princess Juliana

SYDSXM

Sydney Kingsford Smith

Mon 26/10

10:20-14:45

2 stops67h 25m

Simpson Bay Princess Juliana

Fri 30/10

15:45-08:35

2 stops49h 50m

$1,916
Fastest return journey

SydneySan Juan

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

SYDSJU

Sydney Kingsford Smith

Sun 15/11

09:15-16:36

1 stop22h 21m

San Juan Luis Munoz Marin Intl

Thu 3/12

15:46-07:00

1 stop24h 14m

$1,920

SydneyBridgetown

SYD Sydney Kingsford Smith - BGI Bridgetown Grantley Adams Intl

SYDBGI

Sydney Kingsford Smith

Tue 27/10

10:20-13:25

2 stops42h 05m

Bridgetown Grantley Adams Intl

Fri 30/10

15:00-08:35

2 stops50h 35m

$1,971

SydneyPointe-à-Pitre

SYD Sydney Kingsford Smith - PTP Pointe-à-Pitre Le Raizet

SYDPTP

Sydney Kingsford Smith

Wed 28/10

10:20-13:50

2 stops42h 30m

Pointe-à-Pitre Le Raizet

Sun 1/11

15:45-09:35

2 stops50h 50m

$2,032

SydneySimpson Bay

SYD Sydney Kingsford Smith - SXM Simpson Bay Princess Juliana

SYDSXM

Sydney Kingsford Smith

Mon 26/10

11:10-13:23

2 stops65h 13m

Simpson Bay Princess Juliana

Fri 30/10

16:39-09:00

2 stops49h 21m

$2,115

SydneyBridgetown

SYD Sydney Kingsford Smith - BGI Bridgetown Grantley Adams Intl

SYDBGI

Sydney Kingsford Smith

Tue 27/10

11:10-21:59

2 stops49h 49m

Bridgetown Grantley Adams Intl

Fri 30/10

15:52-09:00

2 stops50h 08m

$2,153

SydneyPort of Spain

SYD Sydney Kingsford Smith - POS Port of Spain Piarco Intl

SYDPOS

Sydney Kingsford Smith

Sat 22/8

09:10-23:18

2 stops28h 08m

Port of Spain Piarco Intl

Sat 19/9

15:06-07:05

2 stops49h 59m

$2,157

SydneySanto Domingo

SYD Sydney Kingsford Smith - SDQ Santo Domingo Las Americas

SYDSDQ

Sydney Kingsford Smith

Thu 5/11

11:20-10:09

2 stops37h 49m

Santo Domingo Las Americas

Mon 9/11

16:59-09:00

2 stops49h 01m

$2,182

SydneyKingston

SYD Sydney Kingsford Smith - KIN Kingston Norman Manley

SYDKIN

Sydney Kingsford Smith

Sat 19/9

09:10-12:04

2 stops41h 54m

Kingston Norman Manley

Sat 26/9

17:08-07:05

2 stops46h 57m

$2,193

Flights are sorted by cheapest return flights first.

Deals found on 6/8

Showing 1-10 of 38 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
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

How long is the flight to Caribbean?

On average, a flight from Sydney to Caribbean takes 45 hours 25 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 most popular airlines that fly to Caribbean?

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

United Airlines
United Airlines
From $1,312
American Airlines
American Airlines
From $2,026
Air Canada
Air Canada
From $3,035
British Airways
British Airways
From $2,487

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

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

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

Destination popularity is based on the amount of flight searches to Caribbean in the last few years. This data was updated on 6 August 2026.
The most popular places in Caribbean to fly to are Cuba, Jamaica, The Bahamas, Dominican Republic and Puerto Rico.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated 6 August 2026.
See what other customers who have flown with United Airlines,American Airlines, andAir Canada 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.
United Airlines
7.4
Good
10,075 reviews
Check prices

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Comfort

7.3

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
10,075 reviews
United Airlines
7.4
Good
10,075 reviews
Check prices

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Comfort

7.3

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
11,873 reviews
United Airlines
7.4
Good
10,075 reviews
Check prices

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Comfort

7.3

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
11,433 reviews
United Airlines
7.4
Good
10,075 reviews
Check prices

Overall

7.4

Entertainment

7.1

Boarding

7.7

Crew

8.1

Food

6.7

Comfort

7.3

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 9 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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