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Caribbean Islands

$181+ Cheap flights from San Jose, CA (SJC) 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SJU
Dec 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Cheap flight deals from San Jose to Caribbean Islands

Keep the following information in mind while searching for San Jose to Caribbean Islands flight deals. Data was last updated November 2, 2025.

Round-trip from

$351
(American Airlines)

One-way from

$181
(Delta)

Popular in

June

Cheapest in

September

Average price

$559
From San Jose to Caribbean Islands
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One-way flight from San Jose to Caribbean Islands
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Highest demand for flights based on searches. 9% potential increase in price ($52 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 November 2025
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Find flight deals from San Jose to Caribbean Islands

Cheapest flights from San Jose to Caribbean Islands
Explore the most affordable flight options available from San Jose to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 2025.

This Southwest deal was found by Cheapflights users on 11/2. 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 12/28:25 amSJC - SJU
2 stops12h 10mSouthwest
Tue 12/98:55 amSJU - SJC
2 stops12h 25mSouthwest
Deal found 11/2$390
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/16:25 pmSJC - NAS
2 stops16h 08mUnited Airlines
Mon 12/82:55 pmNAS - SJC
2 stops25h 37mUnited Airlines
Deal found 11/1$446
This Southwest deal was found by Cheapflights users on 11/1. 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 11/198:40 amSJC - SJU
2 stops11h 55mSouthwest
Tue 11/257:30 amSJU - SJC
2 stops12h 25mSouthwest
Deal found 11/1$467
This Southwest deal was found by Cheapflights users on 10/31. 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 12/1811:55 amSJU - SJC
2 stops12h 20mSouthwest
Deal found 10/31$479
This American Airlines deal was found by Cheapflights users on 11/2. 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
2 stops15h 38mAmerican Airlines
Deal found 11/2$483
This Southwest deal was found by Cheapflights users on 11/1. 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 11/198:00 amSJC - SJU
2 stops12h 35mSouthwest
Mon 11/247:40 amSJU - SJC
2 stops14h 35mSouthwest
Deal found 11/1$515
This Southwest deal was found by Cheapflights users on 11/1. 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
Tue 12/211:20 amSJU - SJC
2 stops13h 40mSouthwest
Deal found 11/1$519
This Delta deal was found by Cheapflights users on 10/31. 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 12/164:35 pmSJC - SJU
2 stops16h 23mDelta
Thu 12/181:07 pmSJU - SJC
1 stop13h 48mDelta
Deal found 10/31$520
This Delta deal was found by Cheapflights users on 11/2. 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
Tue 11/183:20 pmSJU - SJC
2 stops12h 32mDelta
Deal found 11/2$525
This Southwest deal was found by Cheapflights users on 10/30. 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 12/310:05 amSJC - SJU
2 stops10h 30mSouthwest
Sun 12/145:40 amSJU - SJC
2 stops12h 00mSouthwest
Deal found 10/30$530
This American Airlines deal was found by Cheapflights users on 11/1. 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 11/196:00 amSJC - SJU
1 stop11h 35mAmerican Airlines
Tue 11/257:15 amSJU - SJC
1 stop17h 34mAmerican Airlines
Deal found 11/1$554
This Delta deal was found by Cheapflights users on 11/2. 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 stops16h 07mDelta
Deal found 11/2$564

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose 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 November 2, 2025.
Use the filters below to find and compare flights from San Jose to Caribbean Islands that are best for you.

Fly from

San Jose

Fly to

Caribbean Islands

Route

Depart

Return

Price

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 3/3

12:50 pm-1:48 pm

2 stops20h 58m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:37 pm-1:22 pm

2 stops24h 45m

$351

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 12/2

8:25 am-12:35 am

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Tue 12/9

8:55 am-5:20 pm

2 stops12h 25m

$390

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 JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 12/1

6:25 pm-1:33 pm

2 stops16h 08m

Nassau Intl

Mon 12/8

2:55 pm-1:32 pm

2 stops25h 37m

$446

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Thu 2/5

11:15 pm-2:32 pm

2 stops12h 17m

Nassau Intl

Sun 2/8

3:35 pm-8:53 am

1 stop20h 18m

$460

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Thu 12/4

7:16 pm-1:01 pm

2 stops13h 45m

San Juan Luis Munoz Marin Intl

Sat 12/13

6:54 am-6:32 pm

2 stops15h 38m

$483

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Thu 2/5

6:00 am-10:26 pm

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Mon 2/9

7:07 am-4:20 pm

1 stop13h 13m

$505

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 12/16

10:25 pm-12:42 pm

1 stop10h 17m

San Juan Luis Munoz Marin Intl

Thu 12/18

3:32 pm-10:55 pm

1 stop11h 23m

$520

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 12/2

8:30 pm-12:42 pm

2 stops12h 12m

San Juan Luis Munoz Marin Intl

Tue 12/9

7:00 am-6:56 pm

2 stops15h 56m

$520

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 11/15

6:30 am-9:00 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Tue 11/18

2:05 am-1:42 pm

2 stops15h 37m

$525

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, December is the cheapest month in which you can book a flight from San Jose, California to Caribbean Islands (average of $169). Flying from San Jose, California to Caribbean Islands in June is currently the most expensive (average of $296). 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 EPX?

Find hourly flight availability from San Jose 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 November 2, 2025.

A simple way to save on the total cost of your ticket is to fly from San Jose, California to Caribbean Islands in the afternoon. If you’re flexible enough to do this you can expect to save up to 19% on your trip compared to booking a flight at noon.

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

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

Travelers seeking maximum savings on their San Jose, California to Caribbean Islands 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 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 November 2, 2025.
Read reviews from past customers who have flown Delta, American Airlines, and Spirit Airlines from San Jose to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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.
Delta
7.9
Good
8,001 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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.
American Airlines
7.2
Good
11,034 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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.
Spirit Airlines
6.3
Okay
8,120 reviews
Delta
7.9
Good
8,001 reviews

Comfort

7.9

Overall

7.9

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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 Jose 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 Jose to Caribbean Islands?

    If you book a flight to Caribbean Islands from San Jose, you will be flying from San Jose, which is the city’s only airport. San Jose (SJC) is located 2.9 mi from the center of San Jose.

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

    A quick flight from San Jose, California to Caribbean Islands can take about 10h 30m. American Airlines provides one of the quickest options available for as low as $425. There are 2732 mi between San Jose, California and Caribbean Islands. 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 Islands one-way?

    The cheapest airlines for a one-way flight from San Jose, California to Caribbean Islands are Delta ($181), Southwest ($205), and American Airlines ($254).

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

    When deciding which route to take from San Jose, California to Caribbean Islands consider San Jose - San Juan Luis Munoz Marin Intl, San Jose - Punta Cana or San Jose - Montego Bay Sangster Intl as they are the most popular.

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from San Jose, California to Caribbean Islands (average of $169). Flying from San Jose, California to Caribbean Islands in June is currently the most expensive (average of $296). 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.

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Alternative routes for San Jose to Caribbean Islands

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Top 5 airlines flying from San Jose to Caribbean Islands

Discover the top 5 airlines that operate flights from San Jose 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 November 2, 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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