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Cheap flights from San José to Caribbean Islands from $105

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 José to Caribbean Islands departing on 2/25. 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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0 bags

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Find the cheapest flights from San José to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Avianca Logo
4:15 pm - 11:35 am
SJO
-
SJU
17h 20m
1 stop
Avianca Logo
4:45 pm - 9:40 pm
SJU
-
SJO
6h 55m
1 stop
$174Avianca
Mon, Mar 9 - Sun, Mar 15
Avianca Logo
1:45 am - 5:05 pm
SJO
-
SJU
13h 20m
1 stop
Avianca Logo
1:00 pm - 12:15 am
SJU
-
SJO
13h 15m
1 stop
$175Avianca
Mon, Mar 9 - Thu, Mar 19
United Airlines Logo
8:45 am - 9:26 pm
SJO
-
SJU
10h 41m
1 stop
United Airlines Logo
7:40 am - 8:39 pm
SJU
-
SJO
14h 59m
1 stop
$182United Airlines
Thu, Feb 19 - Mon, Feb 23
United Airlines Logo
7:55 am - 8:38 pm
SJO
-
SJU
10h 43m
1 stop
United Airlines Logo
1:00 am - 11:38 am
SJU
-
SJO
12h 38m
1 stop
$193United Airlines
Sun, Apr 26 - Tue, Apr 28
American Airlines Logo
2:22 pm - 9:13 am
SJO
-
SJU
16h 51m
1 stop
American Airlines Logo
10:03 am - 7:07 pm
SJU
-
SJO
11h 04m
1 stop
$202American Airlines
Thu, Apr 23 - Tue, Apr 28
Arajet Logo
7:48 pm - 12:45 am
SJO
-
SDQ
2h 57mnonstop
Arajet Logo
5:53 pm - 7:03 pm
SDQ
-
SJO
3h 10mnonstop
$257Arajet
Tue, Mar 10 - Sat, Mar 14
Arajet Logo
7:48 pm - 12:45 am
SJO
-
SDQ
2h 57mnonstop
Arajet Logo
5:53 pm - 7:03 pm
SDQ
-
SJO
3h 10mnonstop
$261Arajet
Sat, Mar 7 - Tue, Mar 17
Copa Airlines Logo
4:09 am - 11:29 am
SJO
-
NAS
5h 20m
1 stop
Copa Airlines Logo
12:30 pm - 4:38 pm
NAS
-
SJO
6h 08m
1 stop
$309Copa Airlines
Mon, Mar 9 - Thu, Mar 12
Copa Airlines Logo
5:51 pm - 10:29 am
SJO
-
NAS
15h 38m
1 stop
Copa Airlines Logo
12:30 pm - 7:01 pm
NAS
-
SJO
8h 31m
1 stop
$320Copa Airlines
Thu, Mar 5 - Mon, Mar 9
American Airlines Logo
6:30 am - 3:37 pm
SJO
-
MBJ
8h 07m
1 stop
American Airlines Logo
12:56 pm - 7:07 pm
MBJ
-
SJO
7h 11m
1 stop
$507American Airlines
Tue, Apr 21 - Wed, Apr 29

American Airlines flights from San José to Caribbean Islands

Our best American Airlines deals on San José to Caribbean Islands flight tickets
American Airlines
Apr 23
SJO2:22 pmSan José Juan Santamaria Intl
16h 51m
1 stop
SJU9:13 amSan Juan Luis Munoz Marin Intl
Apr 28
SJU10:03 amSan Juan Luis Munoz Marin Intl
11h 04m
1 stop
SJO7:07 pmSan José Juan Santamaria Intl
$202
American Airlines
Feb 16
SJO1:31 pmSan José Juan Santamaria Intl
19h 36m
1 stop
MBJ10:07 amMontego Bay Sangster Intl
Feb 18
MBJ11:07 amMontego Bay Sangster Intl
10h 26m
1 stop
SJO8:33 pmSan José Juan Santamaria Intl
$542
American Airlines
Feb 19
SJO1:31 pmSan José Juan Santamaria Intl
19h 36m
1 stop
MBJ10:07 amMontego Bay Sangster Intl
Feb 22
MBJ2:33 pmMontego Bay Sangster Intl
7h 00m
1 stop
SJO8:33 pmSan José Juan Santamaria Intl
$574

Avianca flights from San José to Caribbean Islands

Our best Avianca deals on San José to Caribbean Islands flight tickets
Avianca
Feb 25
SJO1:45 amSan José Juan Santamaria Intl
7h 50m
1 stop
SJU11:35 amSan Juan Luis Munoz Marin Intl
Mar 1
SJU6:30 pmSan Juan Luis Munoz Marin Intl
7h 45m
1 stop
SJO12:15 amSan José Juan Santamaria Intl
$174
Avianca
Mar 9
SJO1:45 amSan José Juan Santamaria Intl
13h 20m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
Mar 19
SJU1:00 pmSan Juan Luis Munoz Marin Intl
13h 15m
1 stop
SJO12:15 amSan José Juan Santamaria Intl
$175
Avianca
Mar 2
SJO1:45 amSan José Juan Santamaria Intl
13h 20m
1 stop
SJU5:05 pmSan Juan Luis Munoz Marin Intl
Mar 20
SJU6:30 pmSan Juan Luis Munoz Marin Intl
16h 20m
1 stop
SJO8:50 amSan José Juan Santamaria Intl
$185

momondo Fare Finder

 
Customize your flight search to find flights from San José 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 February 15, 2026.
Use the filters below to find and compare flights from San José to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Mon 3/9

4:15 pm-11:35 am

1 stop17h 20m

San Juan Luis Munoz Marin Intl

Sun 3/15

4:45 pm-9:40 pm

1 stop6h 55m

$174

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Mon 3/9

1:45 am-5:05 pm

1 stop13h 20m

San Juan Luis Munoz Marin Intl

Thu 3/19

1:00 pm-12:15 am

1 stop13h 15m

$175

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Thu 2/19

8:45 am-9:26 pm

1 stop10h 41m

San Juan Luis Munoz Marin Intl

Mon 2/23

7:40 am-8:39 pm

1 stop14h 59m

$182

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Sun 4/26

7:55 am-8:38 pm

1 stop10h 43m

San Juan Luis Munoz Marin Intl

Tue 4/28

1:00 am-11:38 am

1 stop12h 38m

$193

San JoséSan Juan

SJO - SJU

SJOSJU

San José Juan Santamaria Intl

Thu 4/23

2:22 pm-9:13 am

1 stop16h 51m

San Juan Luis Munoz Marin Intl

Tue 4/28

10:03 am-7:07 pm

1 stop11h 04m

$202

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Tue 3/10

7:48 pm-12:45 am

Nonstop2h 57m

Santo Domingo Las Americas

Sat 3/14

5:53 pm-7:03 pm

Nonstop3h 10m

$257

San JoséSanto Domingo

SJO - SDQ

SJOSDQ

San José Juan Santamaria Intl

Sat 3/7

7:48 pm-12:45 am

Nonstop2h 57m

Santo Domingo Las Americas

Tue 3/17

5:53 pm-7:03 pm

Nonstop3h 10m

$261

San JoséNassau

SJO - NAS

SJONAS

San José Juan Santamaria Intl

Mon 3/9

4:09 am-11:29 am

1 stop5h 20m

Nassau Intl

Thu 3/12

12:30 pm-4:38 pm

1 stop6h 08m

$309

San JoséNassau

SJO - NAS

SJONAS

San José Juan Santamaria Intl

Thu 3/5

5:51 pm-10:29 am

1 stop15h 38m

Nassau Intl

Mon 3/9

12:30 pm-7:01 pm

1 stop8h 31m

$320

San JoséMontego Bay

SJO - MBJ

SJOMBJ

San José Juan Santamaria Intl

Tue 4/21

6:30 am-3:37 pm

1 stop8h 07m

Montego Bay Sangster Intl

Wed 4/29

12:56 pm-7:07 pm

1 stop7h 11m

$507

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 José 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 May is, on average, the cheapest month to fly to Caribbean Islands from San José, with most prices found around $186. The month of June is another great option to travel to Caribbean Islands, with average flight prices from San José averaging around $191.

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

The cheapest day to depart from San José to Caribbean Islands is on a Thursday. Travelers who choose to depart for Caribbean Islands on a Thursday will often find tickets for as low as $208. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $210. 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 San José Juan Santamaria Intl to Caribbean Islands flight route?

Fly from San José Juan Santamaria Intl to Santo Domingo Las Americas for the best San José Juan Santamaria Intl - Caribbean Islands flight prices

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 José when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $236 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 José for as low as $190 on momondo.

What cabin class options are available on San José Juan Santamaria Intl to Caribbean Islands flights?

There is only 1 cabin class available to choose from on San José Juan Santamaria Intl to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on San José to Caribbean Islands flights?

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

Cheap San José to Caribbean Islands flight deals and tips

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

Fastest flight time

2h 57m

Direct flights

Wed, Thu and Sun

Airports in Caribbean Islands

99 airports
The fastest flight from San José to Caribbean Islands takes 2h 57m
Direct flights go from San José to Caribbean Islands on Wednesday, Thursday and Sunday. There are no airlines offering direct flights.
There are 99 airports in Caribbean Islands. From San José there are direct flights to Santo Domingo Las Americas (SDQ).
Search flight deals

  • When did momondo last update prices for flights from San José Juan Santamaria Intl Airport to Caribbean Islands?

    Prices for flights from San José Juan Santamaria Intl Airport to Caribbean Islands were last updated today.

  • How many operators does momondo search for flights from San José Juan Santamaria Intl Airport to Caribbean Islands?

  • How old do you have to be to fly from San José Juan Santamaria Intl Airport to Caribbean Islands?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from San José Juan Santamaria Intl 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 José to Caribbean Islands?

Best airlines flying from San José to Caribbean Islands

Compare and see reviews for airlines that fly from San José to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
ArajetPriceFrom $152Free CancellationRating
6.6
44 reviews
Search Arajet flights
Copa AirlinesPriceFrom $163Free CancellationRating
7.5
1,558 reviews
Search Copa Airlines flights
AviancaPriceFrom $165Free CancellationRating
6.6
2,496 reviews
Search Avianca flights
American AirlinesPriceFrom $510Free CancellationRating
7.2
11,296 reviews
Search American Airlines flights

Why use momondo?

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

Finding the right flight to Caribbean Islands from San José is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Caribbean Islands quick and easy, saving you time and money.

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

All flight searches from San José to Caribbean Islands on momondo can be filtered to show those which offer flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from San José.

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

Yes. momondo can track prices for San José to Caribbean Islands flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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