R11 139+ 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 27/5. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
Apr 27 — May 41
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 28 March 2026.

Sat 9/523:15
JNB
-
SJU
2 stops30h 20m
KLM
Sat 16/57:30
SJU
-
JNB
2 stops31h 50m
KLM
Deal found 25/3R19 815
Mon 11/55:45
JNB
-
SDQ
3 stops42h 10m
Multiple Airlines
Sun 17/512:45
SDQ
-
JNB
3 stops57h 30m
Multiple Airlines
Deal found 24/3R21 269
Mon 21/99:50
JNB
-
SJU
2 stops37h 00m
Etihad Airways
Thu 24/96:00
SJU
-
JNB
2 stops44h 20m
Etihad Airways
Deal found 23/3R22 074
Wed 6/521:15
JNB
-
MBJ
2 stops42h 58m
American Airlines
Tue 12/512:56
MBJ
-
JNB
2 stops35h 04m
American Airlines
Deal found 26/3R23 973
Sat 21/1122:00
JNB
-
SJU
2 stops28h 00m
British Airways
Wed 25/1114:41
SJU
-
JNB
2 stops34h 54m
British Airways
Deal found 27/3R25 051
Wed 22/414:45
JNB
-
SJU
2 stops31h 10m
Multiple Airlines
Sat 9/56:18
SJU
-
JNB
2 stops51h 52m
Multiple Airlines
Deal found 24/3R25 154
Fri 8/521:15
JNB
-
KIN
2 stops52h 39m
British Airways
Tue 12/57:00
KIN
-
JNB
2 stops41h 00m
British Airways
Deal found 24/3R25 222
Fri 8/521:15
JNB
-
MBJ
2 stops45h 09m
American Airlines
Fri 15/516:37
MBJ
-
JNB
2 stops33h 48m
American Airlines
Deal found 24/3R25 427
Fri 1/514:45
JNB
-
STT
2 stops31h 30m
Qatar Airways
Tue 5/515:30
STT
-
JNB
2 stops35h 20m
Qatar Airways
Deal found 23/3R25 616
Thu 22/1014:45
JNB
-
FPO
2 stops28h 10m
Qatar Airways
Mon 26/1015:10
FPO
-
JNB
2 stops30h 45m
Qatar Airways
Deal found 24/3R25 667
Tue 12/517:50
JNB
-
SDQ
2 stops49h 19m
Multiple Airlines
Sun 17/520:32
SDQ
-
JNB
2 stops55h 58m
Multiple Airlines
Deal found 23/3R25 821
Wed 30/921:15
JNB
-
SDQ
2 stops43h 40m
British Airways
Sun 4/1017:25
SDQ
-
JNB
2 stops58h 00m
British Airways
Deal found 26/3R26 659

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 28 March 2026
Explore Caribbean

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 594 507 searches and data was last updated on 28 March 2026.

One-way from

R11 139

Popular in

April

Cheapest in

November

Average price

R22 724
27/5
  • 27/5
  • 3 total stops
  • 46h 44m total
  • Johannesburg to Caribbean
Highest demand for flights based on searches. 1% potential increase in price (R424 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (R571 potential savings vs. average return price).
Average for return flights in March 2026

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 594 507 searches and data was last updated on 28 March 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

JohannesburgSan Juan

JNB - SJU

JNBSJU

Johannesburg OR Tambo

Sat 9/5

23:15-23:35

2 stops30h 20m

San Juan Luis Munoz Marin Intl

Sat 16/5

7:30-21:20

2 stops31h 50m

R19 815

JohannesburgSan Juan

JNB - SJU

JNBSJU

Johannesburg OR Tambo

Mon 21/9

9:50-16:50

2 stops37h 00m

San Juan Luis Munoz Marin Intl

Thu 24/9

6:00-8:20

2 stops44h 20m

R22 074

JohannesburgKingston

JNB - KIN

JNBKIN

Johannesburg OR Tambo

Fri 8/5

21:15-18:54

2 stops52h 39m

Kingston Norman Manley

Tue 12/5

7:00-7:00

2 stops41h 00m

R25 222

JohannesburgMontego Bay

JNB - MBJ

JNBMBJ

Johannesburg OR Tambo

Fri 8/5

21:15-11:24

2 stops45h 09m

Montego Bay Sangster Intl

Fri 15/5

16:37-9:25

2 stops33h 48m

R25 427

JohannesburgSaint Thomas Island

JNB - STT

JNBSTT

Johannesburg OR Tambo

Fri 1/5

14:45-16:15

2 stops31h 30m

Saint Thomas Island Cyril E King

Tue 5/5

15:30-8:50

2 stops35h 20m

R25 616

JohannesburgSanto Domingo

JNB - SDQ

JNBSDQ

Johannesburg OR Tambo

Tue 12/5

17:50-13:09

2 stops49h 19m

Santo Domingo Las Americas

Sun 17/5

20:32-10:30

2 stops55h 58m

R25 821

JohannesburgWillemstad

JNB - CUR

JNBCUR

Johannesburg OR Tambo

Thu 9/4

2:30-15:48

2 stops43h 18m

Willemstad Hato Int.

Fri 17/4

14:42-15:50

2 stops43h 08m

R27 549

JohannesburgOranjestad

JNB - AUA

JNBAUA

Johannesburg OR Tambo

Fri 1/5

14:45-16:16

2 stops31h 31m

Oranjestad Reina Beatrix

Tue 5/5

17:25-8:50

2 stops33h 25m

R28 045

JohannesburgSaint Thomas Island

JNB - STT

JNBSTT

Johannesburg OR Tambo

Sun 13/9

21:15-12:50

2 stops45h 35m

Saint Thomas Island Cyril E King

Thu 17/9

13:50-7:00

2 stops35h 10m

R29 654

JohannesburgSaint Thomas Island

JNB - STT

JNBSTT

Johannesburg OR Tambo

Tue 7/4

12:40-16:15

2 stops33h 35m

Saint Thomas Island Cyril E King

Fri 10/4

12:25-4:00

2 stops33h 35m

R33 025

Flights are sorted by cheapest return flights first.

Deals found on 24/3

Showing 1-10 of 48 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 Johannesburg to Caribbean takes 38 hours 6 minutes. Flights to Caribbean 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 cheapest airlines that fly to Caribbean?

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

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 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 when rainfall is around 40.0 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, 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).

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 28 March 2026.
The most popular places in Caribbean to fly to are Cuba, The Bahamas, Jamaica, Barbados and Dominican Republic.

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 28 March 2026.
See what other customers who have flown with KLM,Virgin Atlantic, andQatar Airways 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.

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

Food

7,3

Overall

7,8

Boarding

7,8

Entertainment

7,1

Crew

8,4

Comfort

7,6

Reviews

1 / 20
2,0
Mediocre

Anonymous,Feb 2026

EZE - SCL

It was a short trip The aeroplane was delay I arrived in Chile late and I lost my fly with Qantas

FAQs about flying to Caribbean

  • What is the best way to travel around the Caribbean?

    If this is a beach-bum holiday on some idyllic beach with cocktails, then the only travelling you’ll be doing is between the hammock in your bungalow and the beach chair. If you’re more adventurous, you might want to look into boat cruises around the Caribbean Sea. For island hopping through the West Indies, you’ll need to fly, so get ready to book flights to the Caribbean.

  • What are some things to do in the Caribbean?

    Aruba, Sint Marten and the many other parts of the West Indies make for perfect beach getaways, while Cuba has long been a sought-after destination for Saffers because it stretches the Rand. When you compare flights to the Caribbean, keep this island in mind. From old cars straight out of the 50s to cobbled streets lined with bars and bistros, UNESCO world heritage site listed Old Havana, and sun-drenched beaches, South Africans love this part of the world.

  • How long is the flight to the Caribbean?

    With no direct flights to the Caribbean from South Africa, you can expect at least one stopover, possibly in Europe or the Middle East. As you search for Caribbean flight deals, consider Sint Maarten, the Bahamas or Aruba as destinations. From Johannesburg’s OR Tambo International Airport (JNB) to Princess Juliana International Airport (SXM) on the island of Sint Maarten, you could look at Caribbean flight deals on KLM via Amsterdam, with a flight time of around 23h 30min. From Cape Town International (CPT) to Queen Beatrix International Airport (AUA) on the island of Aruba, you could look at cheap flights to the Caribbean on British Airways and United via Johannesburg and New York with a flight time of about 28h. To book flights to the Caribbean from Durban’s King Shaka International (DUR) to Jose Marti International Airport in Havana (HAV), compare flights to the Caribbean on British Airways and Air France via Johannesburg and Paris, for a flight time of around 27h.

  • What do I need to do before my flight to the Caribbean?

    Aruba and Sint Marten are part of the Netherlands, so as a Saffer, you will need a Schengen visa. This is quite a lengthy process with several documents (including proof of income, return air ticket, confirmation of accommodation, and medical insurance for the duration of your stay). Your valid South African passport will need to have enough pages available to hold the visa and more than six months from expiring when you return. Looking for Caribbean flight deals and cost-effective Caribbean airfare is the easy part.

  • 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, KLM is rated the highest out of the airlines that fly to Caribbean.

  • What is the cheapest airport to fly to in Caribbean?

    Punta Cana is currently the cheapest airport to fly to in Caribbean. One-way flights to Punta Cana typically cost R2 046, while return flights cost around R4 049.

  • Where does the fastest flight to Caribbean depart from?

    For those looking to save time traveling to Caribbean, Johannesburg offers the quickest one-way flight (26 hours 11 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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Yes! Cheapflights helps users easily find flights to Caribbean with no change fees.

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