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$138+ Cheap flights from San Jose, CA (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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 12/319:56 amSJC - SJU
2 stops19h 39mAmerican Airlines
Mon 1/124:28 pmSJU - SJC
2 stops23h 42mAmerican Airlines
Deal found 10/28$351
This Frontier deal was found by Cheapflights users on 10/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/106:19 pmSJC - SJU
2 stops19h 35mFrontier
Thu 11/133:59 amSJU - SJC
2 stops17h 35mFrontier
Deal found 10/26$366
This Delta deal was found by Cheapflights users on 10/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/156:25 amSJC - SJU
1 stop12h 48mDelta
Wed 11/197:15 amSJU - SJC
2 stops15h 51mDelta
Deal found 10/26$400
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 12/316:35 amSJC - SJU
1 stop12h 45mDelta
Tue 1/137:00 amSJU - SJC
2 stops13h 20mDelta
Deal found 10/28$425
This Delta deal was found by Cheapflights users on 10/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1710:25 pmSJC - NAS
1 stop10h 29mDelta
Thu 11/202:55 pmNAS - SJC
1 stop8h 43mDelta
Deal found 10/27$425
This American Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 12/47:16 pmSJC - SJU
2 stops13h 45mAmerican Airlines
Sat 12/136:54 amSJU - SJC
1 stop17h 34mAmerican Airlines
Deal found 10/28$430
This Southwest deal was found by Cheapflights users on 10/27. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/197:15 pmSJC - SJU
2 stops11h 10mSouthwest
Sat 11/225:35 amSJU - SJC
2 stops13h 05mSouthwest
Deal found 10/27$431
This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/276:30 amSJC - SJU
1 stop10h 30mUnited Airlines
Thu 12/42:25 pmSJU - SJC
1 stop11h 02mUnited Airlines
Deal found 10/26$443
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 12/1510:25 pmSJC - NAS
1 stop14h 18mDelta
Wed 12/244:28 pmNAS - SJC
2 stops19h 42mDelta
Deal found 10/28$451
This Southwest deal was found by Cheapflights users on 10/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/271:15 pmSJC - SJU
2 stops17h 45mSouthwest
Thu 12/48:55 amSJU - SJC
2 stops12h 25mSouthwest
Deal found 10/26$457
This Southwest deal was found by Cheapflights users on 10/28. 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.
Tue 12/167:15 pmSJC - SJU
2 stops11h 10mSouthwest
Thu 12/187:40 amSJU - SJC
2 stops14h 35mSouthwest
Deal found 10/28$464
This Delta deal was found by Cheapflights users on 10/28. 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.
Mon 12/1510:25 pmSJC - NAS
1 stop14h 18mDelta
Thu 12/258:10 amNAS - SJC
2 stops15h 54mDelta
Deal found 10/28$473

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 October 28, 2025.

Round-trip from

$351
(American Airlines)

One-way from

$138
(Delta)

Popular in

June

Cheapest in

September

Average price

$555
From San Jose to Caribbean
Search Deals
One-way flight from San Jose to Caribbean
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($52 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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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 October 28, 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

Sat 11/15

6:25 am-11:13 pm

1 stop12h 48m

San Juan Luis Munoz Marin Intl

Wed 11/19

7:15 am-7:06 pm

2 stops15h 51m

$400

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 1/26

10:30 pm-1:31 pm

1 stop12h 01m

Nassau Intl

Fri 1/30

2:56 pm-9:20 pm

1 stop9h 24m

$425

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Tue 3/3

10:30 pm-12:00 pm

1 stop10h 30m

Nassau Intl

Thu 3/5

2:55 pm-9:32 pm

1 stop9h 37m

$425

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 4/7

9:25 pm-10:35 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Tue 4/21

11:25 am-9:05 pm

2 stops12h 40m

$431

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 2/24

7:30 pm-11:20 am

2 stops11h 50m

San Juan Luis Munoz Marin Intl

Sun 3/8

5:00 am-5:10 pm

1 stop16h 10m

$431

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Sun 2/22

10:30 pm-1:30 pm

1 stop12h 00m

Nassau Intl

Sat 2/28

2:55 pm-9:32 pm

1 stop9h 37m

$450

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Thu 11/27

1:15 pm-11:00 am

2 stops17h 45m

San Juan Luis Munoz Marin Intl

Thu 12/4

8:55 am-5:20 pm

2 stops12h 25m

$457

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 12/15

4:35 pm-11:41 am

2 stops16h 06m

Nassau Intl

Mon 12/22

8:10 am-9:34 pm

1 stop16h 24m

$473

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 11/15

6:30 am-12:36 am

2 stops14h 06m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-1:42 pm

2 stops15h 37m

$490

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Thu 4/9

7:40 pm-9:10 am

2 stops10h 30m

San Juan Luis Munoz Marin Intl

Mon 4/13

6:50 am-5:25 pm

2 stops13h 35m

$495

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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, California to Caribbean?

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Caribbean (average of $169). Flying from San Jose, California to Caribbean in October is currently the most expensive (average of $329). 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 October 28, 2025.

It’s typically best to fly out from San Jose, California to Caribbean in the afternoon. Doing so could potentially save you 18% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly from San Jose, California to Caribbean?

Use this chart to determine the cheapest time to fly round-trip from San Jose to Caribbean. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their San Jose, California to Caribbean flight should consider departing on Thursday afternoons when fares are most often at their lowest. Friday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

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 October 28, 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
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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
8,116 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

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, California to Caribbean?

    Departing from San Jose, California to Caribbean will take you 10h 10m. The distance between San Jose, California and Caribbean is about 3597 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    $138 is the cheapest one-way deal found within the past few days, from American Airlines. You may also be able to find cheap deals on Delta and Alaska Airlines, with prices starting from $138 and $176, respectively.

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

    Most travelers choose San Jose - San Juan Luis Munoz Marin Intl, San Jose - Punta Cana or San Jose - Montego Bay Sangster Intl when deciding on the best route from San Jose, California 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, California to Caribbean?

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Caribbean (average of $169). Flying from San Jose, California to Caribbean in October is currently the most expensive (average of $329). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$232Average$444FlexibilityNo cancel feeOn-time65%
DeltaCheapest$255Average$556FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$298Average$576FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$383Average$557FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$414Average$642FlexibilityNo cancel feeOn-time71%

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