Caribbean Islands

$100+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SJU
Jun 17 — Jun 241
We work with more than 300 partners to bring you better travel deals

Find cheap flights from San José to Caribbean Islands with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap 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 June 12, 2025.

Round-trip from

$164
(Copa Airlines)

One-way from

$100
(FlightHub)

Popular in

January

Cheapest in

May

Average price

$194
From San José Juan Santamaria Intl to Caribbean Islands
One-way flight from San José Juan Santamaria Intl to Caribbean Islands
Highest demand for flights based on searches. 17% potential increase in price ($60 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in June 2025

Find 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 June 12, 2025.

This Copa Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 9/44:10 amSJO - SJU
1 stop9h 48mCopa Airlines
Thu 9/115:31 amSJU - SJO
1 stop15h 28mCopa Airlines
Deal found 6/10$164
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/231:55 amSJO - SJU
1 stop12h 55mAvianca
Mon 7/286:15 pmSJU - SJO
1 stop17h 05mAvianca
Deal found 6/11$166
This Booking.com deal was found by Cheapflights users on 6/10. 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 6/251:55 amSJO - SJU
1 stop12h 55mMultiple Airlines
Sun 6/298:24 pmSJU - SJO
1 stop16h 53mMultiple Airlines
Deal found 6/10$196
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/35:30 amSJO - SJU
1 stop22h 00mUnited Airlines
Sun 7/62:05 amSJU - SJO
1 stop22h 34mUnited Airlines
Deal found 6/10$198
This Copa Airlines deal was found by Cheapflights users on 6/12. 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.
Mon 8/184:10 amSJO - SDQ
1 stop4h 49mCopa Airlines
Sat 8/238:55 amSDQ - SJO
1 stop9h 27mCopa Airlines
Deal found 6/12$231
This Arajet deal was found by Cheapflights users on 6/12. 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 9/205:35 pmSJO - SDQ
Nonstop3h 04mArajet
Sat 9/273:47 pmSDQ - SJO
Nonstop3h 03mArajet
Deal found 6/12$234
This Gotogate deal was found by Cheapflights users on 6/9. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/141:55 amSJO - SDQ
1 stop13h 20mMultiple Airlines
Mon 10/206:32 pmSDQ - SJO
Nonstop3h 03mMultiple Airlines
Deal found 6/9$288
This Arajet deal was found by Cheapflights users on 6/10. 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 7/58:42 amSJO - SJU
1 stop5h 57mArajet
Mon 7/73:20 pmSJU - SJO
1 stop6h 15mArajet
Deal found 6/10$315
This JetBlue deal was found by Cheapflights users on 6/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/181:00 pmSJO - SJU
1 stop8h 12mJetBlue
Sun 7/203:05 amSJU - SJO
1 stop11h 55mJetBlue
Deal found 6/9$322
This Mytrip deal was found by Cheapflights users on 6/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/211:40 amSJO - CUR
1 stop12h 55mAvianca
Sat 9/2711:05 amCUR - SJO
1 stop6h 45mAvianca
Deal found 6/11$335
This Booking.com deal was found by Cheapflights users on 6/11. 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 10/292:15 amSJO - CUR
1 stop6h 00mMultiple Airlines
Sun 11/212:35 pmCUR - SJO
1 stop8h 28mMultiple Airlines
Deal found 6/11$338
This Copa Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 9/15:52 amSJO - AUA
1 stop4h 19mCopa Airlines
Fri 9/51:17 pmAUA - SJO
1 stop7h 42mCopa Airlines
Deal found 6/10$339

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 June 12, 2025.
Use the filters below to find and compare flights from San José to Caribbean Islands that are best for you.

Fly from

San José

Fly to

Caribbean Islands

Route

Depart

Return

Price

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Thu 9/4

4:10 am-1:00 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Thu 9/11

5:31 am-4:52 pm

1 stop13h 21m

$164

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Wed 7/23

1:55 am-4:50 pm

1 stop12h 55m

San Juan Luis Munoz Marin Intl

Mon 7/28

6:15 pm-9:20 am

1 stop17h 05m

$166

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Wed 6/25

1:55 am-4:50 pm

1 stop12h 55m

San Juan Luis Munoz Marin Intl

Sun 6/29

8:24 pm-11:17 am

1 stop16h 53m

$196

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Thu 7/3

5:30 am-5:30 am

1 stop22h 00m

San Juan Luis Munoz Marin Intl

Sun 7/6

2:05 am-10:39 pm

1 stop22h 34m

$198

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Mon 8/18

4:10 am-10:59 am

1 stop4h 49m

Santo Domingo Las Americas

Sat 8/23

8:55 am-4:22 pm

1 stop9h 27m

$231

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Mon 8/18

8:20 pm-1:24 am

Nonstop3h 04m

Santo Domingo Las Americas

Mon 8/25

6:32 pm-7:35 pm

Nonstop3h 03m

$239

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 8/30

5:35 pm-10:39 pm

Nonstop3h 04m

Santo Domingo Las Americas

Tue 9/2

11:45 am-3:50 pm

1 stop6h 05m

$311

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Sat 7/5

8:42 am-4:39 pm

1 stop5h 57m

San Juan Luis Munoz Marin Intl

Mon 7/7

3:20 pm-7:35 pm

1 stop6h 15m

$315

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Fri 7/18

1:00 pm-11:12 pm

1 stop8h 12m

San Juan Luis Munoz Marin Intl

Sun 7/20

3:05 am-1:00 pm

1 stop11h 55m

$322

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Thu 7/10

11:24 am-1:35 am

1 stop12h 11m

San Juan Luis Munoz Marin Intl

Thu 7/17

10:14 pm-11:11 am

1 stop14h 57m

$335

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/12

Showing 1-10 of 59 results
1
2
3
...
6

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, San José Province to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from San José, San José Province to Caribbean Islands (average of $254). Flying from San José, San José Province to Caribbean Islands in June is currently the most expensive (average of $339). 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 June 12, 2025.

When flying from San José, San José Province 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.

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 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.

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, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
To help decide which airline to fly from San José to Caribbean Islands, see what other customers have to say about Delta, Alaska Airlines and Southwest. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
8.0
Very good

Boarding

8.2

Comfort

7.9

Entertainment

7.9

Overall

8.0

Food

7.3

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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.

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

    For one-way options, check prices for Avianca. According to our data, you can fly for as low as $100. Users have also found prices from $119 and $123 on Copa Airlines and United Airlines, respectively.

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

  • What are the cheapest flights from San José, San José Province to Caribbean Islands?

    Looking at all options, your cheapest flight can be booked for $99. While the most popular route (San José Juan Santamaria Intl - San Juan Luis Munoz Marin Intl) can be booked for $168 on average our data indicates $139 when flying from San José, San José Province 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, San José Province to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from San José, San José Province to Caribbean Islands (average of $254). Flying from San José, San José Province to Caribbean Islands in June is currently the most expensive (average of $339). 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.

Alternative routes for San José to Caribbean Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 5 airlines flying from San José to Caribbean Islands

Discover the top 5 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
AviancaCheapest$154Average$361FlexibilityNo cancel feeOn-time71%
Copa AirlinesCheapest$184Average$440FlexibilityNo cancel feeOn-time70%
Spirit AirlinesCheapest$193Average$398FlexibilityNo cancel feeOn-time65%
ArajetCheapest$201Average$261FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$509Average$656FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.