Caribbean Islands

$133+ Cheap flights from San Jose (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 7/19. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SJU
Jul 1 — Jul 81
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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 June 26, 2025.

Round-trip from

$265
(Delta)

One-way from

$133
(Southwest)

Popular in

June

Cheapest in

September

Average price

$633
From San Jose to Caribbean Islands
One-way flight from San Jose to Caribbean Islands
Highest demand for flights based on searches. 8% potential increase in price ($47 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in June 2025

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 June 26, 2025.

This Delta deal was found by Cheapflights users on 6/25. 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.
Sun 8/313:17 pmSJC - SJU
2 stops18h 53mDelta
Sat 9/67:30 amSJU - SJC
2 stops14h 43mDelta
Deal found 6/25$265
This American Airlines deal was found by Cheapflights users on 6/25. 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.
Sat 10/2512:17 pmSJC - SJU
2 stops19h 58mAmerican Airlines
Tue 10/283:55 pmSJU - SJC
2 stops21h 16mAmerican Airlines
Deal found 6/25$314
This Southwest deal was found by Cheapflights users on 6/26. 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.
Sat 11/86:50 amSJC - SJU
1 stop12h 25mSouthwest
Thu 11/137:40 amSJU - SJC
2 stops14h 00mSouthwest
Deal found 6/26$339
This FlightHub deal was found by Cheapflights users on 6/26. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/176:30 amSJC - SJU
2 stops26h 02mSpirit Airlines
Fri 7/181:37 amSJU - SJC
2 stops16h 02mSpirit Airlines
Deal found 6/26$340
This United Airlines deal was found by Cheapflights users on 6/25. 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.
Tue 10/286:40 amSJC - SJU
1 stop10h 20mUnited Airlines
Fri 10/317:30 amSJU - SJC
2 stops16h 23mUnited Airlines
Deal found 6/25$355
This Mytrip deal was found by Cheapflights users on 6/25. 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.
Thu 7/1711:31 amSJC - STT
3 stops24h 39mSpirit Airlines
Wed 7/231:25 pmSTT - SJC
2 stops24h 11mSpirit Airlines
Deal found 6/25$398
This Priceline deal was found by Cheapflights users on 6/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/86:00 amSJC - MBJ
2 stops25h 14mSpirit Airlines
Sun 9/1412:46 pmMBJ - SJC
2 stops12h 31mSpirit Airlines
Deal found 6/26$415
This Delta deal was found by Cheapflights users on 6/26. 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.
Mon 8/1110:58 pmSJC - NAS
1 stop9h 50mDelta
Fri 8/153:05 pmNAS - SJC
1 stop10h 45mDelta
Deal found 6/26$425
This American Airlines deal was found by Cheapflights users on 6/25. 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 7/96:00 amSJC - NAS
2 stops12h 46mAmerican Airlines
Wed 7/1610:36 amNAS - SJC
2 stops10h 53mAmerican Airlines
Deal found 6/25$443
This SmartFares deal was found by Cheapflights users on 6/25. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/284:22 pmSJC - PUJ
2 stops19h 08mSpirit Airlines
Sat 8/21:00 pmPUJ - SJC
2 stops24h 36mSpirit Airlines
Deal found 6/25$446
This Mytrip deal was found by Cheapflights users on 6/25. 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.
Mon 8/181:09 pmSJC - SDQ
2 stops23h 51mSpirit Airlines
Fri 8/225:05 pmSDQ - SJC
3 stops32h 25mSpirit Airlines
Deal found 6/25$511
This Travelocity deal was found by Cheapflights users on 6/25. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/166:00 amSJC - SJU
1 stop14h 25mMultiple Airlines
Sat 7/191:27 amSJU - SJC
1 stop13h 38mMultiple Airlines
Deal found 6/25$541

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 June 26, 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

Sun 8/31

10:25 pm-1:10 pm

1 stop11h 45m

San Juan Luis Munoz Marin Intl

Sat 9/6

7:30 am-7:13 pm

2 stops14h 43m

$265

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 10/25

12:17 pm-11:15 am

2 stops19h 58m

San Juan Luis Munoz Marin Intl

Tue 10/28

3:55 pm-10:11 am

2 stops21h 16m

$314

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 11/8

6:50 am-11:15 pm

1 stop12h 25m

San Juan Luis Munoz Marin Intl

Thu 11/13

7:40 am-5:40 pm

2 stops14h 00m

$339

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Thu 7/17

6:30 am-11:32 am

2 stops26h 02m

San Juan Luis Munoz Marin Intl

Fri 7/18

1:37 am-2:39 pm

2 stops16h 02m

$340

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 10/28

6:40 am-8:00 pm

1 stop10h 20m

San Juan Luis Munoz Marin Intl

Fri 10/31

7:30 am-8:53 pm

2 stops16h 23m

$355

San JoseSaint Thomas Island

SJC - STT

SJCSTT

San Jose

Thu 7/17

11:31 am-3:10 pm

3 stops24h 39m

Saint Thomas Island Cyril E King

Wed 7/23

1:25 pm-10:36 am

2 stops24h 11m

$398

San JoseMontego Bay

SJC - MBJ

SJCMBJ

San Jose

Mon 9/8

6:00 am-9:14 am

2 stops25h 14m

Montego Bay Sangster Intl

Sun 9/14

12:46 pm-11:17 pm

2 stops12h 31m

$415

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Mon 8/11

10:58 pm-11:48 am

1 stop9h 50m

Nassau Intl

Fri 8/15

3:05 pm-10:50 pm

1 stop10h 45m

$425

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Wed 7/9

6:00 am-9:46 pm

2 stops12h 46m

Nassau Intl

Wed 7/16

10:36 am-6:29 pm

2 stops10h 53m

$443

San JosePunta Cana

SJC - PUJ

SJCPUJ

San Jose

Mon 7/28

4:22 pm-2:30 pm

2 stops19h 08m

Punta Cana

Sat 8/2

1:00 pm-10:36 am

2 stops24h 36m

$446

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/25

Showing 1-10 of 53 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 to Caribbean Islands?

Currently, September is the cheapest month in which you can book a flight from San Jose to Caribbean Islands (average of $254). Flying from San Jose 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 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 June 26, 2025.

When flying from San Jose 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.

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 26, 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest, and Delta 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.

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.
8.0
Very good

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

Food

7.1

Overall

8.0

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.1

Reviews

1 / 20
10.0
Excellent

James,Apr 2025

LAX - SFO

Good flight except the uncontrollable cold air from the ceiling.

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.

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

    $133 is the cheapest one-way deal found within the past few days, from Southwest. You may also be able to find cheap deals on American Airlines and Spirit Airlines, with prices starting from $159 and $161, respectively.

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

  • 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 to Caribbean Islands?

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

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Alternative routes for San Jose to Caribbean Islands

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

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 June 26, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$238Average$432FlexibilityNo cancel feeOn-time65%
DeltaCheapest$255Average$574FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$269Average$714FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$328Average$580FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$383Average$573FlexibilityNo cancel feeOn-time63%

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