What is the cheapest airline that flies from San Jose to Caribbean Islands?

American Airlines, Delta, and United Airlines are the most popular carriers operating from San Jose to Caribbean Islands

What airlines fly to Caribbean Islands?

American Airlines, United Airlines and JetBlue are the top three most popular airlines that fly to Caribbean Islands from San Jose, California according to our data. American Airlines is the first choice among our users, with 41% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 11 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

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?

As of July 2026, there are 5 operators available to choose from 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.

$189 Cheap Flights from San Jose, California to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from San Jose, California to Caribbean Islands

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

4:24 pm - 12:03 pm

SJC

SJU

16h 39m

2 stops

7:00 am - 6:48 pm

SJU

SJC

14h 48m

2 stops

$406Delta

Sat, Sep 26 - Tue, Oct 6

6:00 am - 9:55 pm

SJC

SJU

12h 55m

2 stops

3:44 pm - 10:32 pm

SJU

SJC

9h 48m

1 stop

$418American Airlines

Wed, Aug 19 - Fri, Aug 28

8:50 am - 11:45 pm

SJC

SJU

11h 55m

2 stops

6:05 am - 2:25 pm

SJU

SJC

12h 20m

2 stops

$421Southwest

Tue, Oct 27 - Sun, Nov 8

6:19 pm - 12:03 pm

SJC

SJU

14h 44m

2 stops

2:59 pm - 9:22 pm

SJU

SJC

9h 23m

1 stop

$445Delta

Sun, Sep 20 - Thu, Oct 1

6:30 am - 9:10 pm

SJC

SJU

11h 40m

2 stops

5:30 am - 2:25 pm

SJU

SJC

11h 55m

1 stop

$451Southwest

Wed, Sep 23 - Mon, Oct 5

4:00 pm - 2:45 pm

SJC

SJU

19h 45m

2 stops

6:00 am - 10:01 pm

SJU

SJC

19h 01m

2 stops

$461American Airlines

Fri, Sep 25 - Wed, Sep 30

4:00 pm - 1:17 pm

SJC

PLS

42h 17m

2 stops

2:30 pm - 5:43 pm

PLS

SJC

30h 13m

2 stops

$627United Airlines

Mon, Dec 7 - Thu, Dec 10

12:51 pm - 1:33 pm

SJC

NAS

21h 42m

2 stops

2:35 pm - 11:46 am

NAS

SJC

24h 11m

2 stops

$669United Airlines

Tue, Sep 1 - Thu, Sep 3

9:00 am - 4:40 pm

SJC

UVF

27h 40m

2 stops

5:40 pm - 9:11 pm

UVF

SJC

31h 31m

2 stops

$989Air Canada

Tue, Dec 8 - Thu, Dec 10

9:00 am - 4:40 pm

SJC

UVF

27h 40m

2 stops

5:40 pm - 9:11 pm

UVF

SJC

31h 31m

2 stops

$999Air Canada

Tue, Dec 8 - Thu, Dec 10

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Delta flights from San Jose, California to Caribbean Islands

Our best Delta deals on San Jose, California to Caribbean Islands flight tickets

Delta

Sep 26

SJC5:45 pmSan Jose

15h 18m

2 stops

SJU12:03 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU7:00 amSan Juan Luis Munoz Marin Intl

13h 24m

2 stops

SJC5:24 pmSan Jose

$406

Delta

Sep 20

SJC6:19 pmSan Jose

14h 44m

2 stops

SJU12:03 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU2:59 pmSan Juan Luis Munoz Marin Intl

9h 23m

1 stop

SJC9:22 pmSan Jose

$445

Delta

Nov 8

SJC10:40 pmSan Jose

14h 55m

1 stop

MBJ4:35 pmMontego Bay Sangster Intl

Nov 12

MBJ2:20 pmMontego Bay Sangster Intl

11h 38m

1 stop

SJC10:58 pmSan Jose

$452

Southwest flights from San Jose, California to Caribbean Islands

Our best Southwest deals on San Jose, California to Caribbean Islands flight tickets

Southwest

Oct 27

SJC8:50 amSan Jose

11h 55m

2 stops

SJU11:45 pmSan Juan Luis Munoz Marin Intl

Nov 8

SJU6:05 amSan Juan Luis Munoz Marin Intl

12h 20m

2 stops

SJC2:25 pmSan Jose

$421

Southwest

Sep 23

SJC6:30 amSan Jose

11h 40m

2 stops

SJU9:10 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU5:30 amSan Juan Luis Munoz Marin Intl

11h 55m

1 stop

SJC2:25 pmSan Jose

$451

Southwest

Sep 23

SJC6:40 amSan Jose

11h 30m

2 stops

SJU9:10 pmSan Juan Luis Munoz Marin Intl

Oct 5

SJU10:10 amSan Juan Luis Munoz Marin Intl

13h 05m

2 stops

SJC8:15 pmSan Jose

$466

momondo Fare Finder

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

Cheapest round-trip

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sat 9/26

4:24 pm-12:03 pm

2 stops16h 39m

San Juan Luis Munoz Marin Intl

Tue 10/6

7:00 am-6:48 pm

2 stops14h 48m

$406

Quickest round-trip

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 8/19

6:00 am-9:55 pm

2 stops12h 55m

San Juan Luis Munoz Marin Intl

Fri 8/28

3:44 pm-10:32 pm

1 stop9h 48m

$418

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 10/27

8:50 am-11:45 pm

2 stops11h 55m

San Juan Luis Munoz Marin Intl

Sun 11/8

6:05 am-2:25 pm

2 stops12h 20m

$421

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Sun 9/20

6:19 pm-12:03 pm

2 stops14h 44m

San Juan Luis Munoz Marin Intl

Thu 10/1

2:59 pm-9:22 pm

1 stop9h 23m

$445

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 9/23

6:30 am-9:10 pm

2 stops11h 40m

San Juan Luis Munoz Marin Intl

Mon 10/5

5:30 am-2:25 pm

1 stop11h 55m

$451

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Fri 9/25

4:00 pm-2:45 pm

2 stops19h 45m

San Juan Luis Munoz Marin Intl

Wed 9/30

6:00 am-10:01 pm

2 stops19h 01m

$461

San JoseProvidenciales

SJC - PLS

SJCPLS

San Jose

Mon 12/7

4:00 pm-1:17 pm

2 stops42h 17m

Providenciales

Thu 12/10

2:30 pm-5:43 pm

2 stops30h 13m

$627

San JoseNassau

SJC - NAS

SJCNAS

San Jose

Tue 9/1

12:51 pm-1:33 pm

2 stops21h 42m

Nassau Intl

Thu 9/3

2:35 pm-11:46 am

2 stops24h 11m

$669

San JoseCastries

SJC - UVF

SJCUVF

San Jose

Tue 12/8

9:00 am-4:40 pm

2 stops27h 40m

Castries Hewanorra

Thu 12/10

5:40 pm-9:11 pm

2 stops31h 31m

$989

San JoseCastries

SJC - UVF

SJCUVF

San Jose

Tue 12/8

9:00 am-4:40 pm

2 stops27h 40m

Castries Hewanorra

Thu 12/10

5:40 pm-9:11 pm

2 stops31h 31m

$999

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from San Jose, California, with most prices found around $575. The month of January is another great option to travel to Caribbean Islands, with average flight prices from San Jose, California averaging around $597.

How far in advance should I book a flight from San Jose, California 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 $563 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 $298 on momondo.

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

You could potentially save up to 4% on your flight if you consider stops on a San Jose, California to Caribbean Islands flight.

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

Fastest flight time	10h 00m
Direct flights	None

The fastest flight from San Jose, California to Caribbean Islands takes 10h 00m

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

Frequently asked questions about flying from San Jose, California to Caribbean Islands

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?
As of July 2026, there are 5 operators available to choose from 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?
Based on momondo bookings for flights between San Jose, California and Caribbean Islands, the leading plane model is Boeing 737 MAX 8, making up 21.68% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 18.53%, Airbus A321neo with 8.83%, and Airbus A320-100/200 with 6.30%.

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
Delta	PriceFrom $138	Free Cancellation	Rating 7.8 8,481 reviews	Search Delta flights
JetBlue	PriceFrom $369	Free Cancellation	Rating 7.1 3,021 reviews	Search JetBlue flights
American Airlines	PriceFrom $394	Free Cancellation	Rating 7.1 11,838 reviews	Search American Airlines flights
Southwest	PriceFrom $402	Free Cancellation	Rating 8.0 4,236 reviews	Search Southwest flights
Alaska Airlines	PriceFrom $685	Free Cancellation	Rating 7.9 12,704 reviews	Search Alaska 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.