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 39% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 12 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

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

United Airlines, Delta, and Alaska Airlines are the most popular carriers operating from San Jose 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 March 2026, there are 7 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.

$194 Cheap Flights from San Jose to Caribbean Islands in 2026

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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.

6:10 am - 8:51 pm

SJC

SJU

11h 41m

2 stops

11:59 pm - 10:10 am

SJU

SJC

13h 11m

1 stop

$326American Airlines

Tue, Apr 28 - Wed, May 6

8:20 pm - 12:52 pm

SJC

SJU

13h 32m

2 stops

6:15 am - 7:07 pm

SJU

SJC

15h 52m

2 stops

$346Delta

Mon, Apr 13 - Fri, Apr 17

6:19 pm - 12:34 pm

SJC

SJU

15h 15m

2 stops

1:00 am - 1:28 pm

SJU

SJC

15h 28m

2 stops

$359United Airlines

Mon, May 4 - Tue, May 12

6:20 am - 11:13 pm

SJC

SJU

13h 53m

2 stops

1:14 pm - 11:00 pm

SJU

SJC

12h 46m

1 stop

$395Delta

Mon, May 4 - Wed, May 13

2:02 pm - 11:51 am

SJC

MBJ

19h 49m

2 stops

12:56 pm - 10:10 am

MBJ

SJC

23h 14m

2 stops

$397American Airlines

Tue, May 5 - Tue, May 12

9:25 pm - 10:35 am

SJC

SJU

10h 10m

2 stops

8:10 am - 6:15 pm

SJU

SJC

13h 05m

2 stops

$406Southwest

Tue, Apr 28 - Tue, May 5

6:00 am - 11:16 pm

SJC

SJU

14h 16m

1 stop

5:37 am - 1:46 pm

SJU

SJC

11h 09m

1 stop

$415Alaska Airlines

Tue, Jul 7 - Wed, Jul 8

2:34 pm - 4:25 am

SJC

SJU

10h 51m

1 stop

5:45 am - 1:35 pm

SJU

SJC

10h 50m

1 stop

$420Alaska Airlines

Wed, Jun 24 - Thu, Jul 2

2:46 pm - 3:10 pm

SJC

MBJ

22h 24m

2 stops

2:40 pm - 12:00 pm

MBJ

SJC

23h 20m

1 stop

$422United Airlines

Tue, May 5 - Tue, May 12

9:45 pm - 3:00 pm

SJC

PUJ

14h 15m

1 stop

1:40 pm - 7:30 am

PUJ

SJC

20h 50m

2 stops

$493Southwest

Sun, May 10 - Thu, May 14

American Airlines flights from San Jose, California to Caribbean Islands

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

American Airlines

Apr 28

SJC6:00 amSan Jose

14h 02m

1 stop

SJU11:02 pmSan Juan Luis Munoz Marin Intl

May 6

SJU11:59 pmSan Juan Luis Munoz Marin Intl

13h 11m

1 stop

SJC10:10 amSan Jose

$326

American Airlines

May 5

SJC2:02 pmSan Jose

19h 49m

2 stops

MBJ11:51 amMontego Bay Sangster Intl

May 12

MBJ12:56 pmMontego Bay Sangster Intl

23h 14m

2 stops

SJC10:10 amSan Jose

$397

American Airlines

May 2

SJC6:00 amSan Jose

14h 02m

1 stop

SJU11:02 pmSan Juan Luis Munoz Marin Intl

May 9

SJU11:59 pmSan Juan Luis Munoz Marin Intl

13h 11m

1 stop

SJC10:10 amSan Jose

$409

Southwest flights from San Jose, California to Caribbean Islands

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

Southwest

Apr 28

SJC9:25 pmSan Jose

10h 10m

2 stops

SJU10:35 amSan Juan Luis Munoz Marin Intl

May 5

SJU8:10 amSan Juan Luis Munoz Marin Intl

13h 05m

2 stops

SJC6:15 pmSan Jose

$406

Southwest

Apr 22

SJC8:20 amSan Jose

12h 20m

2 stops

SJU11:40 pmSan Juan Luis Munoz Marin Intl

Apr 30

SJU2:00 pmSan Juan Luis Munoz Marin Intl

11h 25m

2 stops

SJC10:25 pmSan Jose

$424

Southwest

Apr 27

SJC9:45 pmSan Jose

12h 25m

1 stop

SJU1:10 pmSan Juan Luis Munoz Marin Intl

May 3

SJU5:00 amSan Juan Luis Munoz Marin Intl

16h 05m

1 stop

SJC6:05 pmSan Jose

$425

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

Tue 4/28

6:10 am-8:51 pm

2 stops11h 41m

San Juan Luis Munoz Marin Intl

Wed 5/6

11:59 pm-10:10 am

1 stop13h 11m

$326

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Mon 4/13

8:20 pm-12:52 pm

2 stops13h 32m

San Juan Luis Munoz Marin Intl

Fri 4/17

6:15 am-7:07 pm

2 stops15h 52m

$346

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Mon 5/4

6:19 pm-12:34 pm

2 stops15h 15m

San Juan Luis Munoz Marin Intl

Tue 5/12

1:00 am-1:28 pm

2 stops15h 28m

$359

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Mon 5/4

6:20 am-11:13 pm

2 stops13h 53m

San Juan Luis Munoz Marin Intl

Wed 5/13

1:14 pm-11:00 pm

1 stop12h 46m

$395

San JoseMontego Bay

SJC - MBJ

SJCMBJ

San Jose

Tue 5/5

2:02 pm-11:51 am

2 stops19h 49m

Montego Bay Sangster Intl

Tue 5/12

12:56 pm-10:10 am

2 stops23h 14m

$397

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 4/28

9:25 pm-10:35 am

2 stops10h 10m

San Juan Luis Munoz Marin Intl

Tue 5/5

8:10 am-6:15 pm

2 stops13h 05m

$406

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Tue 7/7

6:00 am-11:16 pm

1 stop14h 16m

San Juan Luis Munoz Marin Intl

Wed 7/8

5:37 am-1:46 pm

1 stop11h 09m

$415

Quickest round-trip

San JoseSan Juan

SJC - SJU

SJCSJU

San Jose

Wed 6/24

2:34 pm-4:25 am

1 stop10h 51m

San Juan Luis Munoz Marin Intl

Thu 7/2

5:45 am-1:35 pm

1 stop10h 50m

$420

San JoseMontego Bay

SJC - MBJ

SJCMBJ

San Jose

Tue 5/5

2:46 pm-3:10 pm

2 stops22h 24m

Montego Bay Sangster Intl

Tue 5/12

2:40 pm-12:00 pm

1 stop23h 20m

$422

San JosePunta Cana

SJC - PUJ

SJCPUJ

San Jose

Sun 5/10

9:45 pm-3:00 pm

1 stop14h 15m

Punta Cana

Thu 5/14

1:40 pm-7:30 am

2 stops20h 50m

$493

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 January is, on average, the cheapest month to fly to Caribbean Islands from San Jose, California, with most prices found around $300. The month of September is another great option to travel to Caribbean Islands, with average flight prices from San Jose, California averaging around $304.

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 $488 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 $236 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

Fastest flight time	9h 45m
Direct flights	None

The fastest flight from San Jose, California to Caribbean Islands takes 9h 45m

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?
As of March 2026, there are 7 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 21.95% of the total bookings. Other popular models include Boeing 737-800 Passenger/BBJ2 (winglets) with 17.95%, Airbus A321neo with 6.74%, and Boeing 737-800 with 5.21%.

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 Airlines	PriceFrom $213	Free Cancellation	Rating 6.3 8,513 reviews	Search Spirit Airlines flights
Delta	PriceFrom $216	Free Cancellation	Rating 7.9 8,276 reviews	Search Delta flights
United Airlines	PriceFrom $298	Free Cancellation	Rating 7.4 9,409 reviews	Search United Airlines flights
Alaska Airlines	PriceFrom $313	Free Cancellation	Rating 8.0 12,018 reviews	Search Alaska Airlines flights
JetBlue	PriceFrom $369	Free Cancellation	Rating 7.2 2,900 reviews	Search JetBlue flights
Southwest	PriceFrom $409	Free Cancellation	Rating 8.0 4,317 reviews	Search Southwest flights
American Airlines	PriceFrom $414	Free Cancellation	Rating 7.1 11,414 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.