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Caribbean Islands

$132+ Cheap flights from San José (SJO) 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SJU
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
1 adult, Economy
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Cheap flight deals from San José to Caribbean Islands

Cheapest flights from San José to Caribbean Islands
Explore the most affordable flight options available from San José to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 27, 2026.

This Booking.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:23 am
SJO
-
SDQ
Nonstop2h 57m
Arajet
Sat 11/144:00 pm
SDQ
-
SJO
Nonstop3h 08m
Arajet
Deal found 7/23$258
This CheapOair deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/411:23 am
SJO
-
SDQ
Nonstop2h 57m
Arajet
Tue 11/104:00 pm
SDQ
-
SJO
Nonstop3h 08m
Arajet
Deal found 7/22$271
This Arajet deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:23 am
SJO
-
SDQ
Nonstop2h 57m
Arajet
Tue 11/174:00 pm
SDQ
-
SJO
Nonstop3h 08m
Arajet
Deal found 7/24$281
This Arajet deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:48 pm
SJO
-
SDQ
Nonstop3h 04m
Arajet
Tue 8/46:00 pm
SDQ
-
SJO
Nonstop3h 03m
Arajet
Deal found 7/23$302
This Copa Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/125:55 pm
SJO
-
SDQ
1 stop6h 30m
Copa Airlines
Tue 9/156:06 am
SDQ
-
SJO
1 stop4h 58m
Copa Airlines
Deal found 7/27$303
This Copa Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:17 pm
SJO
-
SJU
1 stop19h 57m
Copa Airlines
Sun 8/236:17 pm
SJU
-
SJO
1 stop14h 53m
Copa Airlines
Deal found 7/22$306
This Arajet deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/285:53 pm
SJO
-
SDQ
Nonstop2h 57m
Arajet
Sat 12/54:00 pm
SDQ
-
SJO
Nonstop3h 08m
Arajet
Deal found 7/22$317
This Copa Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2910:03 am
SJO
-
SJU
1 stop10h 26m
Copa Airlines
Sat 9/56:16 pm
SJU
-
SJO
1 stop16h 48m
Copa Airlines
Deal found 7/23$317
This Copa Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:08 am
SJO
-
SJU
1 stop10h 06m
Copa Airlines
Sun 8/166:17 pm
SJU
-
SJO
1 stop18h 41m
Copa Airlines
Deal found 7/26$318
This Arajet deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:48 pm
SJO
-
SDQ
Nonstop3h 04m
Arajet
Wed 7/299:35 am
SDQ
-
SJO
Nonstop3h 03m
Arajet
Deal found 7/23$323
This Copa Airlines deal was found by Cheapflights users on 7/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2612:02 pm
SJO
-
SDQ
1 stop12h 06m
Copa Airlines
Sat 1/27:05 pm
SDQ
-
SJO
1 stop17h 55m
Copa Airlines
Deal found 7/22$324
This Arajet deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/295:53 pm
SJO
-
SDQ
Nonstop2h 57m
Arajet
Sat 1/24:00 pm
SDQ
-
SJO
Nonstop3h 08m
Arajet
Deal found 7/27$328

Find flight deals from San José to Caribbean Islands

Keep the following information in mind while searching for San José to Caribbean Islands flight deals. Data was last updated July 27, 2026.

Round-trip from

$258
(Booking.com)

One-way from

$138
(Booking.com)

Popular in

July

Cheapest in

September

Average price

$388
From San José Juan Santamaria Intl to Caribbean Islands
Search Deals
One-way flight from San José Juan Santamaria Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($48 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San José to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
Use the filters below to find and compare flights from San José to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 9/19

5:45 am-1:13 pm

1 stop5h 28m

Santo Domingo Las Americas

Wed 9/23

6:41 pm-8:19 am

1 stop15h 38m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Tue 9/8

5:55 pm-4:15 pm

1 stop20h 20m

Santo Domingo Las Americas

Tue 9/15

6:06 am-9:04 am

1 stop4h 58m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 10/3

5:45 am-1:12 pm

1 stop5h 27m

Santo Domingo Las Americas

Tue 10/6

12:12 pm-6:59 pm

1 stop8h 47m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Wed 11/11

12:04 pm-10:58 pm

1 stop8h 54m

Santo Domingo Las Americas

Sat 11/14

2:24 pm-8:19 am

1 stop19h 55m

$303
Quickest round-trip

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 8/29

5:45 am-1:13 pm

1 stop5h 28m

Santo Domingo Las Americas

Tue 9/1

12:42 pm-4:49 pm

1 stop6h 07m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Wed 9/16

8:12 am-2:25 am

1 stop16h 13m

Santo Domingo Las Americas

Sat 9/19

12:12 pm-6:24 pm

1 stop8h 12m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 10/10

5:45 am-1:12 pm

1 stop5h 27m

Santo Domingo Las Americas

Sat 10/17

2:16 pm-7:10 am

1 stop18h 54m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Tue 12/1

6:03 pm-11:02 am

1 stop14h 59m

Santo Domingo Las Americas

Sat 12/12

12:43 pm-6:59 pm

1 stop8h 16m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 12/19

12:02 pm-2:08 am

1 stop12h 06m

Santo Domingo Las Americas

Sat 1/2

7:05 pm-7:02 am

1 stop13h 57m

$303

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 1/23

2:15 pm-2:04 am

1 stop9h 49m

Santo Domingo Las Americas

Sat 1/30

7:05 pm-7:22 am

1 stop14h 17m

$303

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 60 resultsSorted by cheapest first
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Best time to book a flight from San José to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from San José with our price prediction graph.
Estimated round-trip 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 from San José to Caribbean Islands

What is the cheapest month to book a flight from San José to Caribbean Islands?

Currently, October is the cheapest month in which you can book a flight from San José to Caribbean Islands (average of $368). Flying from San José to Caribbean Islands in August is currently the most expensive (average of $440). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from SJO to EPX?

Find hourly flight availability from San José to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 27, 2026.

When flying from San José to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

How far ahead should I book a flight from San José to Caribbean Islands?

The best time to book flights from San José to Caribbean Islands is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 July 27, 2026.
See what other customers who have flown with Copa Airlines,American Airlines, andAvianca from San José to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,561 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

Food

6.9

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Copa Airlines
7.6
Good
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

Food

6.9

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
American Airlines
7.1
Good
11,840 reviews
Copa Airlines
7.6
Good
1,561 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

Food

6.9

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Avianca
6.5
Okay
2,521 reviews
Copa Airlines
7.6
Good
1,561 reviews

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

Food

6.9

Entertainment

6.8

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines

Related info for your journey

Find useful and relevant information for your journey from San José to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from San José to Caribbean Islands?

    San José Juan Santamaria Intl (SJO), located 8.8 mi from the city center, is the airport you fly out of when you book flights from San José to Caribbean Islands.

  • How long is the flight from San José to Caribbean Islands?

    Departing from San José to Caribbean Islands will take you 6h 30m. San José and Caribbean Islands are separated by a distance of 1133 mi.

  • What are the cheapest airlines to fly from San José to Caribbean Islands one-way?

    To fly one-way, consider booking your trip with Avianca, which is currently one of the cheapest options available, starting at $120. Arajet flights start at $120 while deals on Copa Airlines start at $142 one-way.

  • What are the most popular routes from San José to Caribbean Islands?

    Most travelers choose San José Juan Santamaria Intl - Punta Cana, San José Juan Santamaria Intl - Oranjestad Reina Beatrix or San José Juan Santamaria Intl - Santo Domingo Las Americas when deciding on the best route from San José to Caribbean Islands.

  • Can I find deals for flights from San José to Caribbean Islands that include hotel bookings?

    Yes. In addition to deals on San José to Caribbean Islands flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San José to Caribbean Islands?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San José to Caribbean Islands.

  • Can I find deals for business class flights from San José to Caribbean Islands?

    Yes. Cheapflights offers flight deals from San José to Caribbean Islands by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from San José to Caribbean Islands?

    Currently, October is the cheapest month in which you can book a flight from San José to Caribbean Islands (average of $368). Flying from San José to Caribbean Islands in August is currently the most expensive (average of $440). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from San José to Caribbean Islands

Discover the top 4 airlines that operate flights from San José to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
ArajetCheapest$176Average$298FlexibilityNo cancel feeOn-timeN/A
Copa AirlinesCheapest$184Average$490FlexibilityNo cancel feeOn-time70%
AviancaCheapest$195Average$387FlexibilityNo cancel feeOn-time71%
American AirlinesCheapest$560Average$900FlexibilityNo cancel feeOn-time71%

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