R14 736+ Cheap flights to Caribbean

— SJU
Oct 21 — Oct 281
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

Thu 5/1122:00 -
1 stop23h 14m
Sun 8/1114:54 -
2 stops44h 41m
Deal found 16/9R21 283
Thu 12/1119:35 -
2 stops33h 51m
Mon 16/117:08 -
2 stops44h 17m
Deal found 16/9R23 428
Tue 22/1222:00 -
1 stop23h 06m
Mon 28/1216:18 -
2 stops59h 22m
Deal found 18/9R29 212
Tue 3/1118:50 -
2 stops30h 45m
Tue 10/1116:40 -
3 stops36h 20m
Deal found 19/9R29 650
Tue 3/1122:00 -
2 stops44h 18m
Tue 10/1113:15 -
2 stops47h 20m
Deal found 19/9R30 365
Sat 3/1023:15 -
1 stop23h 55m
Wed 7/1018:55 -
2 stops33h 25m
Deal found 17/9R33 452
Sat 3/1018:55 -
2 stops47h 23m
Wed 7/1019:21 -
2 stops56h 29m
Deal found 17/9R33 468
Sun 20/1219:35 -
2 stops32h 16m
Sun 27/1222:05 -
2 stops28h 35m
Deal found 16/9R36 068
Sun 20/1222:00 -
1 stop31h 46m
Sun 27/1214:53 -
1 stop21h 42m
Deal found 16/9R38 911
Fri 16/1014:05 -
2 stops52h 24m
Fri 23/1013:10 -
2 stops37h 30m
Deal found 18/9R41 884
Tue 22/1215:35 -
3 stops38h 22m
Mon 28/1217:05 -
3 stops33h 45m
Deal found 18/9R43 606

Find flights to Caribbean

Explore Caribbean

Find flight deals to Caribbean

One-way from

R18 797

Popular in

August

Cheapest in

May

Average price

R22 745
British Airways
  • British Airways
  • 13/10-31/12
  • 2 total stops
  • 47h 33m total
  • Johannesburg to Caribbean
Highest demand for flights based on searches. 14% potential increase in price (R3 825 potential increase over avg. return price).
Cheapest flight prices on average. 2% potential price decrease (R515 potential savings vs. average return price).
Average for return flights in September 2026

Cheapflights Fare Finder

 
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

JohannesburgFreeport

JNB Johannesburg OR Tambo - FPO Freeport Grand Bahama Intl

JNBFPO

Johannesburg OR Tambo

Tue 10/11

20:20-11:21

2 stops46h 01m

Freeport Grand Bahama Intl

Wed 31/12

0:00-7:00

Nonstop0h 00m

R16 913

JohannesburgFreeport

JNB Johannesburg OR Tambo - FPO Freeport Grand Bahama Intl

JNBFPO

Johannesburg OR Tambo

Sat 3/10

14:05-11:07

2 stops51h 02m

Freeport Grand Bahama Intl

Wed 31/12

0:00-7:00

Nonstop0h 00m

R17 157

JohannesburgSaint Thomas Island

JNB Johannesburg OR Tambo - STT Saint Thomas Island Cyril E King

JNBSTT

Johannesburg OR Tambo

Mon 12/10

20:55-14:55

2 stops48h 00m

Saint Thomas Island Cyril E King

Wed 31/12

0:00-6:00

Nonstop0h 00m

R19 009

JohannesburgSaint Thomas Island

JNB Johannesburg OR Tambo - STT Saint Thomas Island Cyril E King

JNBSTT

Johannesburg OR Tambo

Fri 22/1

10:25-17:50

2 stops37h 25m

Saint Thomas Island Cyril E King

Sat 30/1

15:00-18:35

2 stops45h 35m

R19 431
Fastest return journey

JohannesburgSaint Thomas Island

JNB Johannesburg OR Tambo - STT Saint Thomas Island Cyril E King

JNBSTT

Johannesburg OR Tambo

Sun 11/10

21:55-13:37

1 stop21h 42m

Saint Thomas Island Cyril E King

Wed 31/12

0:00-6:00

Nonstop0h 00m

R19 610

JohannesburgSaint Thomas Island

JNB Johannesburg OR Tambo - STT Saint Thomas Island Cyril E King

JNBSTT

Johannesburg OR Tambo

Sun 11/10

21:15-12:58

2 stops45h 43m

Saint Thomas Island Cyril E King

Wed 31/12

0:00-6:00

Nonstop0h 00m

R20 146

JohannesburgSanto Domingo

JNB Johannesburg OR Tambo - SDQ Santo Domingo Las Americas

JNBSDQ

Johannesburg OR Tambo

Thu 4/2

22:00-23:46

1 stop31h 46m

Santo Domingo Las Americas

Mon 8/2

14:53-18:35

1 stop21h 42m

R21 234

JohannesburgMontego Bay

JNB Johannesburg OR Tambo - MBJ Montego Bay Sangster Intl

JNBMBJ

Johannesburg OR Tambo

Thu 5/11

22:00-14:14

1 stop23h 14m

Montego Bay Sangster Intl

Sun 8/11

14:54-18:35

2 stops44h 41m

R21 283

JohannesburgOranjestad

JNB Johannesburg OR Tambo - AUA Oranjestad Reina Beatrix

JNBAUA

Johannesburg OR Tambo

Wed 27/1

15:05-15:15

2 stops30h 10m

Oranjestad Reina Beatrix

Sun 31/1

15:00-18:35

2 stops45h 35m

R21 429

JohannesburgSan Juan

JNB Johannesburg OR Tambo - SJU San Juan Luis Munoz Marin Intl

JNBSJU

Johannesburg OR Tambo

Sun 24/1

18:50-1:53

2 stops37h 03m

San Juan Luis Munoz Marin Intl

Thu 28/1

10:43-11:00

2 stops42h 17m

R21 527

Flights are sorted by cheapest return flights first.

Deals found on 21/9

Showing 1-10 of 34 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

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 39 hours 43 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 Air Europa, British Airways and United Airlines.

Rainfall in Caribbean 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

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).

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

To ensure you get the cheapest price possible for a flight to Caribbean, you should look to book at least 71 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.

What are the most popular places to fly to in Caribbean?

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

Reviews of airlines servicing Caribbean

See what other customers who have flown with SWISS,United Airlines, 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

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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.

Food

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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.

Food

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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.

Food

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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.

Food

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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.

Food

7,1

Comfort

7,4

Overall

7,5

Entertainment

6,8

Boarding

7,7

Crew

8,2

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

  • 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, Air Europa 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 R1 942, while return flights cost around R1 853.

  • 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 (23 hours 6 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?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights to Caribbean. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

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

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights to Caribbean for you. Better yet — we are completely free to use.

Can Cheapflights find flights to Caribbean with no change fees?

Yes! Cheapflights helps users easily find flights to Caribbean with no change fees.

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

Yes, and it’s super simple to set up Price Alerts. Click the bell icon next to the flight deals above and provide your email address. That’s it!

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