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Cheap flights from San Jose, California to Caribbean Islands from $138

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from San Jose, California to Caribbean Islands departing on 1/26. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from San Jose, California to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
2:25 pm - 12:58 pmSJC-SJU
18h 33m2 stops
Delta Logo
7:00 am - 8:36 pmSJU-SJC
17h 36m2 stops
$275Delta
Find Deal
Sat, Dec 6 - Wed, Dec 10
Delta Logo
3:45 pm - 1:00 pmSJC-SJU
17h 15m2 stops
Delta Logo
7:00 am - 6:51 pmSJU-SJC
15h 51m2 stops
$352Delta
Find Deal
Mon, Feb 2 - Tue, Feb 10
American Airlines Logo
6:00 am - 10:22 pmSJC-SJU
12h 22m1 stop
American Airlines Logo
6:00 am - 1:47 pmSJU-SJC
11h 47m2 stops
$390American Airlines
Find Deal
Tue, Feb 3 - Tue, Feb 10
Southwest Logo
8:25 am - 12:35 amSJC-SJU
12h 10m2 stops
Southwest Logo
11:20 am - 9:00 pmSJU-SJC
13h 40m2 stops
$409Southwest
Find Deal
Wed, Dec 10 - Wed, Dec 17
American Airlines Logo
7:16 pm - 1:01 pmSJC-SJU
13h 45m2 stops
American Airlines Logo
6:25 am - 6:32 pmSJU-SJC
16h 07m2 stops
$430American Airlines
Find Deal
Thu, Dec 4 - Sat, Dec 13
Southwest Logo
7:10 am - 12:35 amSJC-SJU
13h 25m2 stops
Southwest Logo
11:20 am - 8:15 pmSJU-SJC
12h 55m2 stops
$431Southwest
Find Deal
Fri, Dec 5 - Mon, Dec 8
United Airlines Logo
6:40 pm - 12:49 pmSJC-SJU
14h 09m2 stops
United Airlines Logo
8:10 am - 8:53 pmSJU-SJC
16h 43m2 stops
$432United Airlines
Find Deal
Sun, Nov 9 - Sat, Nov 15
Alaska Airlines Logo
6:00 am - 9:25 pmSJC-SJU
11h 25m1 stop
Alaska Airlines Logo
7:00 am - 1:47 pmSJU-SJC
10h 47m1 stop
$461Alaska Airlines
Find Deal
Wed, Dec 10 - Wed, Jan 14
United Airlines Logo
6:40 pm - 12:49 pmSJC-SJU
14h 09m2 stops
United Airlines Logo
2:05 am - 1:42 pmSJU-SJC
15h 37m2 stops
$480United Airlines
Find Deal
Sun, Nov 9 - Fri, Nov 14
Alaska Airlines Logo
6:00 am - 10:22 pmSJC-SJU
12h 22m1 stop
Alaska Airlines Logo
3:59 pm - 12:09 pmSJU-SJC
24h 10m2 stops
$547Alaska Airlines
Find Deal
Mon, Feb 2 - Mon, Feb 9

Frontier flights from San Jose, California to Caribbean Islands

Our best Frontier deals on San Jose, California to Caribbean Islands flight tickets
Frontier
Nov 7
SJC12:27 pmSan Jose
19h 49m
2 stops
SJU12:16 pmSan Juan Luis Munoz Marin Intl
Nov 9
SJU10:39 pmSan Juan Luis Munoz Marin Intl
16h 53m
2 stops
SJC11:32 amSan Jose
$498
Find similar
Frontier
Dec 12
SJC3:27 pmSan Jose
22h 56m
2 stops
SJU6:23 pmSan Juan Luis Munoz Marin Intl
Dec 25
SJU6:00 amSan Juan Luis Munoz Marin Intl
16h 48m
2 stops
SJC6:48 pmSan Jose
$518
Find similar
Frontier
Oct 27
SJC12:35 pmSan Jose
19h 44m
2 stops
SJU11:19 amSan Juan Luis Munoz Marin Intl
Oct 30
SJU10:39 pmSan Juan Luis Munoz Marin Intl
15h 53m
2 stops
SJC11:32 amSan Jose
$537
Find similar

Southwest flights from San Jose, California to Caribbean Islands

Our best Southwest deals on San Jose, California to Caribbean Islands flight tickets
Southwest
Dec 10
SJC8:25 amSan Jose
12h 10m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Dec 17
SJU11:20 amSan Juan Luis Munoz Marin Intl
13h 40m
2 stops
SJC9:00 pmSan Jose
$409
Find similar
Southwest
Dec 5
SJC7:10 amSan Jose
13h 25m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Dec 8
SJU11:20 amSan Juan Luis Munoz Marin Intl
12h 55m
2 stops
SJC8:15 pmSan Jose
$431
Find similar
Southwest
Jan 14
SJC8:25 amSan Jose
12h 10m
2 stops
SJU12:35 amSan Juan Luis Munoz Marin Intl
Jan 21
SJU12:10 pmSan Juan Luis Munoz Marin Intl
12h 55m
2 stops
SJC9:05 pmSan Jose
$447
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from San Jose, California 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, momondo users made 832,500 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from San Jose, California to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 12/6

2:25 pm-12:58 pm

2 stops18h 33m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-8:36 pm

2 stops17h 36m

$275

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Mon 2/2

3:45 pm-1:00 pm

2 stops17h 15m

San Juan Luis Munoz Marin Intl

Tue 2/10

7:00 am-6:51 pm

2 stops15h 51m

$352

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 2/3

6:00 am-10:22 pm

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Tue 2/10

6:00 am-1:47 pm

2 stops11h 47m

$390

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 12/10

8:25 am-12:35 am

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Wed 12/17

11:20 am-9:00 pm

2 stops13h 40m

$409

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

6:25 am-6:32 pm

2 stops16h 07m

$430

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Fri 12/5

7:10 am-12:35 am

2 stops13h 25m

San Juan Luis Munoz Marin Intl

Mon 12/8

11:20 am-8:15 pm

2 stops12h 55m

$431

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sun 11/9

6:40 pm-12:49 pm

2 stops14h 09m

San Juan Luis Munoz Marin Intl

Sat 11/15

8:10 am-8:53 pm

2 stops16h 43m

$432

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 12/10

6:00 am-9:25 pm

1 stop11h 25m

San Juan Luis Munoz Marin Intl

Wed 1/14

7:00 am-1:47 pm

1 stop10h 47m

$461

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sun 11/9

6:40 pm-12:49 pm

2 stops14h 09m

San Juan Luis Munoz Marin Intl

Fri 11/14

2:05 am-1:42 pm

2 stops15h 37m

$480

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Mon 2/2

6:00 am-10:22 pm

1 stop12h 22m

San Juan Luis Munoz Marin Intl

Mon 2/9

3:59 pm-12:09 pm

2 stops24h 10m

$547

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from San Jose, California to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from San Jose, California, with most prices found around $319. The month of January is another great option to travel to Caribbean Islands, with average flight prices from San Jose, California averaging around $374.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from San Jose, California to Caribbean Islands is on a Sunday. Travelers who choose to depart for Caribbean Islands on a Sunday will often find tickets for as low as $485. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $663. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is at noon. momondo users have found flights departing from San Jose, California to Caribbean Islands at noon for as low as $487. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $597. Of course, these prices can vary depending on the time of year and what airport you fly to.

How far in advance should I book a flight to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from San Jose, California when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $522 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from San Jose, California for as low as $226 on momondo.

Can stopping save me money on San Jose, California to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between San Jose, California to Caribbean Islands.

Cheap San Jose, California to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from San Jose, California to Caribbean Islands

Direct flights

None
There are no direct flights from San Jose, California to Caribbean Islands. There are no popular flight routes from San Jose, California to Caribbean Islands.
Search flight deals

  • When did momondo last update prices for flights from San Jose Airport to Caribbean Islands?

    Prices for flights from San Jose Airport to Caribbean Islands are updated daily.

  • How many operators does momondo search for flights from San Jose Airport to Caribbean Islands?

  • How old do you have to be to fly from San Jose Airport to Caribbean Islands?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from San Jose Airport to Caribbean Islands.

  • What documentation or ID do you need to fly to Caribbean Islands?

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from San Jose, California to Caribbean Islands?

Best airlines flying from San Jose, California to Caribbean Islands

Compare and see reviews for airlines that fly from San Jose, California to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $232Free CancellationRating
6.3
8,097 reviews
Search Spirit Airlines flights
DeltaPriceFrom $255Free CancellationRating
7.9
7,984 reviews
Search Delta flights
United AirlinesPriceFrom $332Free CancellationRating
7.4
8,982 reviews
Search United Airlines flights
SouthwestPriceFrom $383Free CancellationRating
8.0
4,241 reviews
Search Southwest flights
American AirlinesPriceFrom $414Free CancellationRating
7.2
11,043 reviews
Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from San Jose to Caribbean Islands?

It is quick and easy to find San Jose to Caribbean Islands flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Caribbean Islands that suits you.

Can I find flights from San Jose to Caribbean Islands with flexible booking policies on momondo?

Yes. All flights to Caribbean Islands from San Jose on momondo can be compared and filtered by various policies on offer, including flexible booking.

How can momondo help me find flights from San Jose to Caribbean Islands?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from San Jose to Caribbean Islands.

I’m not ready to book a flight from San Jose to Caribbean Islands right now. Can momondo alert me if prices change?

If you are not ready to book a flight from San Jose to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

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