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R15 349+ 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
Aug 24 — Aug 311
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 25 July 2026.

Sun 8/1118:50
JNB
-
SJU
2 stops31h 55m
Turkish Airlines
Wed 11/1116:00
SJU
-
JNB
2 stops48h 25m
Turkish Airlines
Deal found 24/7R20 650
Sun 8/1122:00
JNB
-
MBJ
2 stops46h 48m
United Airlines
Sun 15/1115:45
MBJ
-
JNB
2 stops43h 50m
United Airlines
Deal found 24/7R21 895
Thu 5/1118:50
JNB
-
KIN
2 stops53h 08m
Multiple Airlines
Thu 12/1118:30
KIN
-
JNB
2 stops57h 30m
Multiple Airlines
Deal found 24/7R22 838
Thu 17/910:25
JNB
-
SDQ
2 stops42h 21m
United Airlines
Mon 21/96:00
SDQ
-
JNB
1 stop30h 30m
United Airlines
Deal found 22/7R23 073
Sun 22/1119:35
JNB
-
MBJ
2 stops45h 41m
American Airlines
Fri 4/1216:23
MBJ
-
JNB
2 stops35h 02m
American Airlines
Deal found 20/7R23 410
Thu 30/719:25
JNB
-
KIN
1 stop29h 10m
British Airways
Fri 7/819:55
KIN
-
JNB
1 stop30h 30m
British Airways
Deal found 22/7R23 444
Sun 8/1120:20
JNB
-
SJU
2 stops46h 03m
Qatar Airways
Wed 11/1116:00
SJU
-
JNB
2 stops41h 35m
Qatar Airways
Deal found 20/7R25 497
Sun 22/1122:00
JNB
-
MBJ
1 stop23h 14m
United Airlines
Fri 4/1213:25
MBJ
-
JNB
1 stop22h 10m
United Airlines
Deal found 20/7R25 665
Tue 13/1021:55
JNB
-
MBJ
1 stop21h 12m
Delta
Tue 20/1014:45
MBJ
-
JNB
1 stop21h 55m
Delta
Deal found 23/7R25 682
Thu 19/1119:35
JNB
-
STT
2 stops46h 37m
British Airways
Mon 23/1113:07
STT
-
JNB
2 stops39h 18m
British Airways
Deal found 24/7R25 783
Tue 18/819:25
JNB
-
KIN
2 stops30h 01m
British Airways
Mon 24/86:05
KIN
-
JNB
2 stops41h 55m
British Airways
Deal found 20/7R26 288
Sun 20/921:55
JNB
-
MBJ
1 stop20h 53m
Delta
Sun 4/1013:14
MBJ
-
JNB
1 stop23h 26m
Delta
Deal found 23/7R26 490

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 25 July 2026
Explore Caribbean Islands
Flights to Montego Bay
Flights to Kingston
Flights to San Juan
Flights to Santo Domingo
Flights to Saint Thomas Island

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 594 507 searches and data was last updated on 25 July 2026.

One-way from

R15 349

Popular in

June

Cheapest in

May

Average price

R26 187
5/9
  • 5/9
  • 2 total stops
  • 39h 45m total
  • Johannesburg to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 8% potential increase in price (R1 975 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (R545 potential savings vs. average return price).
Search Deals
Average for return flights in July 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 594 507 searches and data was last updated on 25 July 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

JohannesburgSan Juan

JNB - SJU

JNBSJU

Johannesburg OR Tambo

Sun 8/11

18:50-20:45

2 stops31h 55m

San Juan Luis Munoz Marin Intl

Wed 11/11

16:00-22:25

2 stops48h 25m

R20 650

JohannesburgMontego Bay

JNB - MBJ

JNBMBJ

Johannesburg OR Tambo

Sun 8/11

22:00-13:48

2 stops46h 48m

Montego Bay Sangster Intl

Sun 15/11

15:45-18:35

2 stops43h 50m

R21 895

JohannesburgKingston

JNB - KIN

JNBKIN

Johannesburg OR Tambo

Wed 4/11

0:20-16:58

2 stops47h 38m

Kingston Norman Manley

Thu 12/11

18:30-11:00

2 stops57h 30m

R22 838

JohannesburgSanto Domingo

JNB - SDQ

JNBSDQ

Johannesburg OR Tambo

Thu 17/9

10:25-22:46

2 stops42h 21m

Santo Domingo Las Americas

Mon 21/9

6:00-18:30

1 stop30h 30m

R23 073
Fastest return journey

JohannesburgMontego Bay

JNB - MBJ

JNBMBJ

Johannesburg OR Tambo

Tue 13/10

21:55-12:07

1 stop21h 12m

Montego Bay Sangster Intl

Tue 20/10

14:45-19:40

1 stop21h 55m

R25 682

JohannesburgSaint Thomas Island

JNB - STT

JNBSTT

Johannesburg OR Tambo

Thu 19/11

19:35-12:12

2 stops46h 37m

Saint Thomas Island Cyril E King

Mon 23/11

13:07-10:25

2 stops39h 18m

R25 783

JohannesburgKingston

JNB - KIN

JNBKIN

Johannesburg OR Tambo

Tue 18/8

19:25-18:26

2 stops30h 01m

Kingston Norman Manley

Mon 24/8

6:05-7:00

2 stops41h 55m

R26 288

JohannesburgMontego Bay

JNB - MBJ

JNBMBJ

Johannesburg OR Tambo

Sun 20/9

21:55-11:48

1 stop20h 53m

Montego Bay Sangster Intl

Sun 4/10

13:14-19:40

1 stop23h 26m

R26 490

JohannesburgMontego Bay

JNB - MBJ

JNBMBJ

Johannesburg OR Tambo

Tue 13/10

14:05-16:12

2 stops33h 07m

Montego Bay Sangster Intl

Tue 20/10

11:45-9:10

2 stops38h 25m

R26 978

JohannesburgKingston

JNB - KIN

JNBKIN

Johannesburg OR Tambo

Mon 7/9

21:55-20:10

1 stop29h 15m

Kingston Norman Manley

Mon 14/9

9:10-19:40

1 stop27h 30m

R27 163

Flights are sorted by cheapest return flights first.

Deals found on 21/7

Showing 1-10 of 34 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 Johannesburg to Caribbean Islands takes 39 hours 13 minutes. Flights to Caribbean Islands from other popular cities in South Africa 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 Johannesburg to Caribbean Islands are British Airways, Qatar Airways and United Airlines.

British Airways
British Airways
From R16 746
Qatar Airways
Qatar Airways
From R23 049
United Airlines
United Airlines
From R15 473
KLM
KLM
From R11 196

What are the cheapest airlines that fly to Caribbean Islands?

The cheapest airlines flying from Johannesburg to Caribbean Islands are United Airlines, KLM and British Airways.

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 40.0 - 180.0 mm per month. September is typically the wettest month, when rainfall can reach 180.0 mm. January is typically the driest time to visit Caribbean Islands when rainfall is around 40.0 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, July 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 21.0 C).

When is the best time to book a flight to Caribbean Islands?

To ensure you get the cheapest price possible for a flight to Caribbean Islands, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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 25 July 2026.
Read through reviews of airlines serving Caribbean Islands, such as SWISS,United Airlines, andQatar Airways. 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.
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.
SWISS
7,5
Good
2 019 reviews
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.
United Airlines
7,4
Good
10 034 reviews
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.
Qatar Airways
7,3
Good
3 747 reviews
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.
American Airlines
7,1
Good
11 846 reviews
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.
British Airways
6,7
Okay
8 132 reviews
SWISS
7,5
Good
2 019 reviews
Check prices

Boarding

7,7

Entertainment

6,8

Food

7,1

Overall

7,5

Comfort

7,4

Crew

8,3

Reviews

1 / 20
4,0
Okay

robert,Sept 2023

BOS - ZRH

Swiss seems to be always late. Pilot said plane came in late. I saw the plane come in 1 hour and a half before take off, no people on board. We almost missed our connection.

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, KLM 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, Johannesburg offers the quickest one-way flight (21 hours 12 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?

Cheapflights makes it easy to find Caribbean Islands flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

Why should you use Cheapflights to find cheap flight tickets to Caribbean Islands?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Caribbean Islands.

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

Yes, we can. To see specific flights to Caribbean Islands with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Caribbean Islands 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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