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$138+ Cheap flights from San Jose (SJC) 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 12/31. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from San Jose to Caribbean

Keep the following information in mind while searching for San Jose to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$275
(American Airlines)

One-way from

$138
(Delta)

Popular in

June

Cheapest in

September

Average price

$350
From San Jose to Caribbean
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One-way flight from San Jose to Caribbean
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Highest demand for flights based on searches. 9% potential increase in price ($54 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from San Jose to Caribbean

Cheapest flights from San Jose to Caribbean
Explore the most affordable flight options available from San Jose to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:10 amSJC - SJU
2 stops13h 42mAmerican Airlines
Wed 12/2410:03 pmSJU - SJC
2 stops16h 00mAmerican Airlines
Deal found 9/10$275
This Delta deal was found by Cheapflights users on 9/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/910:25 pmSJC - SJU
1 stop10h 18mDelta
Wed 12/246:30 amSJU - SJC
2 stops20h 05mDelta
Deal found 9/10$302
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/14:37 pmSJC - SJU
2 stops17h 19mDelta
Sat 11/87:00 amSJU - SJC
2 stops15h 48mDelta
Deal found 9/11$349
This United Airlines deal was found by Cheapflights users on 9/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/226:22 pmSJC - SJU
2 stops14h 38mUnited Airlines
Wed 10/297:10 amSJU - SJC
2 stops13h 28mUnited Airlines
Deal found 9/9$366
This Southwest deal was found by Cheapflights users on 9/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/227:30 amSJC - SJU
2 stops13h 20mSouthwest
Wed 10/296:10 amSJU - SJC
1 stop14h 55mSouthwest
Deal found 9/9$380
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/96:10 amSJC - SJU
2 stops13h 42mAmerican Airlines
Wed 12/241:30 amSJU - SJC
1 stop12h 33mAmerican Airlines
Deal found 9/10$382
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2311:40 amSJC - SJU
3 stops30h 16mSpirit Airlines
Fri 9/2610:42 amSJU - SJC
2 stops27h 03mSpirit Airlines
Deal found 9/10$410
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/223:15 pmSJC - SJU
2 stops16h 51mAmerican Airlines
Wed 10/295:00 pmSJU - SJC
2 stops19h 21mAmerican Airlines
Deal found 9/9$422
This United Airlines deal was found by Cheapflights users on 9/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/16:22 pmSJC - SJU
2 stops15h 12mUnited Airlines
Thu 10/232:00 pmSJU - SJC
1 stop10h 06mUnited Airlines
Deal found 9/11$435
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/56:45 amSJC - SJU
2 stops14h 30mSouthwest
Thu 10/95:50 amSJU - SJC
1 stop13h 10mSouthwest
Deal found 9/10$447
This Mytrip deal was found by Cheapflights users on 9/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2311:40 amSJC - SDQ
2 stops25h 20mMultiple Airlines
Fri 9/2610:19 amSDQ - SJC
3 stops36h 41mMultiple Airlines
Deal found 9/10$467
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Mon 11/174:02 pmSJC - NAS
2 stops16h 51mUnited Airlines
Sun 11/232:55 pmNAS - SJC
2 stops22h 10mUnited Airlines
Deal found 9/10$473

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Caribbean 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 September 11, 2025.
Use the filters below to find and compare flights from San Jose to Caribbean that are best for you.

Fly from

San Jose

Fly to

Caribbean

Route

Depart

Return

Price

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 3/3

6:09 am-11:30 pm

2 stops13h 21m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:25 pm-9:28 am

2 stops21h 03m

$351

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 10/22

6:22 pm-12:00 pm

2 stops14h 38m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:05 am-1:42 pm

2 stops15h 37m

$400

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Fri 2/20

10:30 pm-11:53 am

1 stop9h 23m

San Juan Luis Munoz Marin Intl

Wed 2/25

7:00 am-6:51 pm

2 stops15h 51m

$423

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 1/26

10:30 pm-1:30 pm

1 stop12h 00m

Nassau Intl

Thu 1/29

1:25 pm-9:32 pm

1 stop11h 07m

$425

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Tue 3/3

10:30 pm-1:30 pm

1 stop12h 00m

Nassau Intl

Thu 3/5

2:55 pm-9:32 pm

1 stop9h 37m

$425

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sun 10/5

6:45 am-12:15 am

2 stops14h 30m

San Juan Luis Munoz Marin Intl

Thu 10/9

5:50 am-4:00 pm

1 stop13h 10m

$447

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Thu 1/8

2:28 pm-9:40 am

2 stops16h 12m

Nassau Intl

Tue 1/13

7:35 am-6:38 pm

2 stops14h 03m

$454

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Thu 1/8

5:00 pm-1:15 pm

2 stops17h 15m

Nassau Intl

Tue 1/13

2:55 pm-9:32 pm

1 stop9h 37m

$454

San JoseSanto Domingo

SJC - SDQ

SJCSDQ

San Jose

Tue 9/23

11:40 am-4:00 pm

2 stops25h 20m

Santo Domingo Las Americas

Fri 9/26

10:19 am-8:00 pm

3 stops36h 41m

$467

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 11/17

4:02 pm-11:53 am

2 stops16h 51m

Nassau Intl

Sun 11/23

2:55 pm-10:05 am

2 stops22h 10m

$473

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Showing 1-10 of 60 results
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Best time to book a flight from San Jose to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from San Jose 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 Jose to Caribbean

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

Currently, September is the cheapest month in which you can book a flight from San Jose to Caribbean (average of $254). Flying from San Jose to Caribbean 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 SJC to CB?

Find hourly flight availability from San Jose to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 11, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from San Jose to Caribbean as you normally would.

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 September 11, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from San Jose to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,023 reviews
Southwest
8.0
Very good
4,248 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Comfort

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from San Jose to Caribbean. 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 Jose to Caribbean?

    Located just 2.9 mi from the city center, San Jose (SJC) is the airport most travelers will use when flying to Caribbean from San Jose.

  • How long is the flight from San Jose to Caribbean?

    Airlines like American Airlines, United Airlines, and Delta fly from San Jose to Caribbean in about 9h 23m. The time it takes to get you to your destination can typically vary by up to 5h 15m. The distance from San Jose to Caribbean is about 3597 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $212. Users have also found prices from $253 and $332 on Southwest and United Airlines, respectively.

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

    Most travelers choose San Jose - San Juan Luis Munoz Marin Intl, San Jose - Punta Cana or San Jose - Nassau Intl when deciding on the best route from San Jose to Caribbean.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from San Jose to Caribbean 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 Jose to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from San Jose to Caribbean (average of $254). Flying from San Jose to Caribbean 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

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Alternative routes for San Jose to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 5 airlines flying from San Jose to Caribbean

Discover the top 5 airlines that operate flights from San Jose to Caribbean. 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$232Average$468FlexibilityNo cancel feeOn-time65%
DeltaCheapest$255Average$574FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$328Average$594FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$383Average$564FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$414Average$606FlexibilityNo cancel feeOn-time71%

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