$132+ Cheap flights from San José (SJO) 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 6/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SJU
Jun 30 — Jul 71
Round-trip
1 adult, Economy
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Find cheap flights from San José to Caribbean Islands with Cheapflights
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Cheapest flights from San José to Caribbean IslandsExplore the most affordable flight options available from San José to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 31, 2026.
Explore the most affordable flight options available from San José to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 31, 2026.
This Mytrip deal was found by Cheapflights users on 5/26. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 8/86:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/26![Arajet logo]()
$292
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:14 am
SJO
- SDQ
1 stop16h 11m
Copa Airlines
Sat 7/48:53 am
SDQ
- SJO
1 stop9h 58m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$293
This Booking.com deal was found by Cheapflights users on 5/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/205:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 10/244:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$294
This Booking.com deal was found by Cheapflights users on 5/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Tue 7/76:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$299
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 9/264:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/27![Arajet logo]()
$300
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/276:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/27![Arajet logo]()
$301
This Gotogate deal was found by Cheapflights users on 5/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/287:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 8/86:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$304
This Booking.com deal was found by Cheapflights users on 5/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/206:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/29![Arajet logo]()
$305
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 7/299:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$307
This CheapOair deal was found by Cheapflights users on 5/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/276:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 7/19:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$312
This United Airlines deal was found by Cheapflights users on 5/27. 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.
Fri 9/47:55 am
SJO
- SJU
2 stops28h 49m
United Airlines
Fri 9/113:56 pm
SJU
- SJO
2 stops45h 42m
United Airlines
Deal found 5/27![United Airlines logo]()
$351
Best flights from San José to Caribbean IslandsDiscover carefully curated flight deals from San José to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 31, 2026.
Discover carefully curated flight deals from San José to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 31, 2026.
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:45 am
SJO
- SDQ
1 stop12h 11m
Copa Airlines
Sat 10/242:16 pm
SDQ
- SJO
1 stop20h 03m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$293
This Arajet deal was found by Cheapflights users on 5/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/135:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Tue 10/204:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$307
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/295:48 pm
SJO
- PUJ
1 stop8h 07m
Multiple Airlines
Sat 9/57:45 am
PUJ
- SJO
1 stop11h 18m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$487
This Copa Airlines deal was found by Cheapflights users on 5/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/294:08 am
SJO
- SDQ
1 stop7h 05m
Copa Airlines
Wed 8/512:43 pm
SDQ
- SJO
1 stop8h 16m
Copa Airlines
Deal found 5/29![Copa Airlines logo]()
$293
This Arajet deal was found by Cheapflights users on 5/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 7/299:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$307
This Copa Airlines deal was found by Cheapflights users on 5/26. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:14 am
SJO
- SDQ
1 stop16h 11m
Copa Airlines
Sat 7/46:42 pm
SDQ
- SJO
1 stop19h 39m
Copa Airlines
Deal found 5/26![Copa Airlines logo]()
$293
This Arajet deal was found by Cheapflights users on 5/27. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 7/46:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/27![Arajet logo]()
$307
This Copa Airlines deal was found by Cheapflights users on 5/27. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/54:08 am
SJO
- SDQ
1 stop5h 34m
Copa Airlines
Tue 8/186:07 am
SDQ
- SJO
1 stop14h 52m
Copa Airlines
Deal found 5/27![Copa Airlines logo]()
$293
This Arajet deal was found by Cheapflights users on 5/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 7/256:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$307
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Sun 8/232:56 pm
SJO
- GCM
1 stop21h 14m
American Airlines
Sun 9/2012:00 pm
GCM
- SJO
1 stop9h 07m
American Airlines
Deal found 5/29![American Airlines logo]()
$813
This Arajet deal was found by Cheapflights users on 5/29. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/195:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 9/264:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/29![Arajet logo]()
$313
This Arajet deal was found by Cheapflights users on 5/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Tue 7/286:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$313
This Copa Airlines deal was found by Cheapflights users on 5/31. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:57 pm
SJO
- SJU
1 stop16h 50m
Copa Airlines
Fri 6/196:17 pm
SJU
- SJO
1 stop16h 04m
Copa Airlines
Deal found 5/31![Copa Airlines logo]()
$359
This Arajet deal was found by Cheapflights users on 5/26. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/2911:23 am
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 8/59:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/26![Arajet logo]()
$313
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/238:12 am
SJO
- SJU
1 stop12h 17m
Copa Airlines
Wed 9/306:16 pm
SJU
- SJO
1 stop21h 35m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Thu 11/52:20 pm
SJO
- GCM
3 stops46h 25m
United Airlines
Tue 11/105:45 pm
GCM
- SJO
2 stops27h 08m
United Airlines
Deal found 5/28![United Airlines logo]()
$1,117
This Copa Airlines deal was found by Cheapflights users on 5/27. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/128:48 am
SJO
- SJU
1 stop5h 21m
Copa Airlines
Mon 11/166:14 pm
SJU
- SJO
1 stop16h 05m
Copa Airlines
Deal found 5/27![Copa Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 5/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:03 am
SJO
- SJU
1 stop10h 26m
Copa Airlines
Sun 9/65:33 am
SJU
- SJO
1 stop5h 31m
Copa Airlines
Deal found 5/29![Copa Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 5/27. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:37 am
SJO
- SJU
1 stop8h 32m
Copa Airlines
Tue 11/176:14 pm
SJU
- SJO
1 stop16h 53m
Copa Airlines
Deal found 5/27![Copa Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 5/26. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/298:11 am
SJO
- SJU
1 stop12h 17m
Copa Airlines
Mon 11/26:14 pm
SJU
- SJO
1 stop21h 39m
Copa Airlines
Deal found 5/26![Copa Airlines logo]()
$359
This FlightHub deal was found by Cheapflights users on 5/29. 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.
Sun 8/239:40 am
SJO
- GCM
2 stops24h 55m
Multiple Airlines
Sun 9/206:10 pm
GCM
- SJO
2 stops15h 20m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$813
This American Airlines deal was found by Cheapflights users on 5/30. 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 7/183:37 pm
SJO
- MBJ
1 stop20h 32m
American Airlines
Sat 7/255:14 pm
MBJ
- SJO
1 stop20h 57m
American Airlines
Deal found 5/30![American Airlines logo]()
$836
This Copa Airlines deal was found by Cheapflights users on 5/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/144:08 am
SJO
- SJU
1 stop10h 06m
Copa Airlines
Tue 8/186:17 pm
SJU
- SJO
1 stop18h 41m
Copa Airlines
Deal found 5/30![Copa Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 5/26. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:08 am
SJO
- SJU
1 stop10h 06m
Copa Airlines
Mon 8/106:17 pm
SJU
- SJO
1 stop18h 41m
Copa Airlines
Deal found 5/26![Copa Airlines logo]()
$359
This CheapOair deal was found by Cheapflights users on 5/26. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/179:25 am
SJO
- MBJ
2 stops25h 19m
Multiple Airlines
Thu 9/243:10 pm
MBJ
- SJO
2 stops33h 45m
Multiple Airlines
Deal found 5/26![Multiple Airlines logo]()
$880
This Copa Airlines deal was found by Cheapflights users on 5/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/38:12 am
SJO
- SJU
1 stop6h 02m
Copa Airlines
Sun 9/65:33 am
SJU
- SJO
1 stop5h 31m
Copa Airlines
Deal found 5/29![Copa Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/174:08 am
SJO
- SJU
1 stop6h 39m
Copa Airlines
Mon 7/206:17 pm
SJU
- SJO
1 stop20h 04m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Fri 11/611:28 pm
SJO
- GCM
2 stops40h 02m
United Airlines
Thu 11/125:45 pm
GCM
- SJO
2 stops44h 10m
United Airlines
Deal found 5/28![United Airlines logo]()
$1,168
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Thu 11/52:20 pm
SJO
- GCM
3 stops46h 25m
United Airlines
Sat 11/75:30 pm
GCM
- SJO
2 stops42h 55m
United Airlines
Deal found 5/28![United Airlines logo]()
$1,206
This Copa Airlines deal was found by Cheapflights users on 5/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/12:48 pm
SJO
- NAS
1 stop18h 44m
Copa Airlines
Tue 9/812:40 pm
NAS
- SJO
1 stop8h 19m
Copa Airlines
Deal found 5/29![Copa Airlines logo]()
$438
Last-minute flights from San José to Caribbean IslandsDiscover last-minute flight deals from San José to Caribbean Islands. Data last updated May 31, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Caribbean Islands. Data last updated May 31, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/28. 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.
Wed 6/312:30 am
SJO
- SJU
1 stop26h 59m
United Airlines
Sat 6/67:00 am
SJU
- SJO
1 stop14h 37m
United Airlines
Deal found 5/28![United Airlines logo]()
$351
This CheapOair deal was found by Cheapflights users on 5/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/276:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$311
This Arajet deal was found by Cheapflights users on 5/30. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/135:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/206:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$328
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/155:57 pm
SJO
- SJU
1 stop20h 17m
Copa Airlines
Fri 6/196:17 pm
SJU
- SJO
1 stop16h 04m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$359
This Booking.com deal was found by Cheapflights users on 5/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/206:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/29![Arajet logo]()
$305
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 6/276:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/27![Arajet logo]()
$301
This Arajet deal was found by Cheapflights users on 5/29. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 6/249:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/29![Arajet logo]()
$320
This Copa Airlines deal was found by Cheapflights users on 5/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:14 am
SJO
- SDQ
1 stop16h 11m
Copa Airlines
Sat 7/48:53 am
SDQ
- SJO
1 stop9h 58m
Copa Airlines
Deal found 5/28![Copa Airlines logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 7/19:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$312
This Booking.com deal was found by Cheapflights users on 5/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Tue 7/76:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$299
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 7/46:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/28![Arajet logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 5/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Wed 7/19:35 am
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 5/30![Arajet logo]()
$327
One-way flights from San José to Caribbean IslandsSearch for one-way flight options from San José to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 31, 2026.
Search for one-way flight options from San José to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/307:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Deal found 5/27![Arajet logo]()
$132
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- CUR
2 stops7h 42m
Arajet
Deal found 5/27![Arajet logo]()
$150
This Booking.com deal was found by Cheapflights users on 5/30. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/185:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Deal found 5/30![Arajet logo]()
$159
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:49 pm
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 5/27![Arajet logo]()
$160
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1111:23 am
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 5/28![Arajet logo]()
$171
This Booking.com deal was found by Cheapflights users on 5/28. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- SDQ
Nonstop3h 04m
Arajet
Deal found 5/28![Arajet logo]()
$172
This Gotogate deal was found by Cheapflights users on 5/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/177:49 pm
SJO
- CUR
2 stops23h 11m
Arajet
Deal found 5/28![Arajet logo]()
$177
This Arajet deal was found by Cheapflights users on 5/29. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/207:48 pm
SJO
- PUJ
1 stop6h 07m
Multiple Airlines
Deal found 5/29![Multiple Airlines logo]()
$181
This FlightHub deal was found by Cheapflights users on 5/29. 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.
Tue 7/287:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Deal found 5/29![Arajet logo]()
$183
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/77:48 pm
SJO
- SDQ
Nonstop3h 04m
Arajet
Deal found 5/28![Arajet logo]()
$188
This Booking.com deal was found by Cheapflights users on 5/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- AUA
1 stop6h 07m
Arajet
Deal found 5/27![Arajet logo]()
$190
This Arajet deal was found by Cheapflights users on 5/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1711:23 am
SJO
- PUJ
1 stop6h 32m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$191
Find flight deals from San José to Caribbean Islands
Keep the following information in mind while searching for San José to Caribbean Islands flight deals. Data was last updated May 31, 2026.
Round-trip from | $292 (Mytrip) |
|---|---|
One-way from | $132 (Kiwi.com) |
Popular in | December |
Cheapest in | June |
Average price | $284 |
Cheapflights 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, Cheapflights users made 2,558,603 searches. Data last updated May 31, 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
Cheapest round-trip
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Tue 10/20
8:45 am-10:56 pm
1 stop12h 11m
Santo Domingo Las Americas
Sat 10/24
2:16 pm-8:19 am
1 stop20h 03m
$293
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Wed 7/29
4:08 am-1:13 pm
1 stop7h 05m
Santo Domingo Las Americas
Wed 8/5
12:43 pm-6:59 pm
1 stop8h 16m
$293
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Sat 6/27
8:14 am-2:25 am
1 stop16h 11m
Santo Domingo Las Americas
Sat 7/4
6:42 pm-12:21 pm
1 stop19h 39m
$293
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Wed 8/5
4:08 am-11:42 am
1 stop5h 34m
Santo Domingo Las Americas
Tue 8/18
6:07 am-6:59 pm
1 stop14h 52m
$293
Quickest round-trip
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Tue 10/13
5:48 pm-10:52 pm
Nonstop3h 04m
Santo Domingo Las Americas
Tue 10/20
4:00 pm-5:03 pm
Nonstop3h 03m
$307
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Tue 7/21
7:48 pm-12:52 am
Nonstop3h 04m
Santo Domingo Las Americas
Wed 7/29
9:35 am-10:38 am
Nonstop3h 03m
$307
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Sat 6/27
7:48 pm-12:52 am
Nonstop3h 04m
Santo Domingo Las Americas
Sat 7/4
6:00 pm-7:03 pm
Nonstop3h 03m
$307
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Tue 7/21
7:48 pm-12:52 am
Nonstop3h 04m
Santo Domingo Las Americas
Sat 7/25
6:00 pm-7:03 pm
Nonstop3h 03m
$307
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Sat 9/19
5:48 pm-10:52 pm
Nonstop3h 04m
Santo Domingo Las Americas
Sat 9/26
4:00 pm-5:03 pm
Nonstop3h 03m
$313
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Tue 7/21
7:48 pm-12:52 am
Nonstop3h 04m
Santo Domingo Las Americas
Tue 7/28
6:00 pm-7:03 pm
Nonstop3h 03m
$313
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San José to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from San José with our price prediction graph.
SJO-SDQ
SJO-SJU
SJO-CUR
SJO-PUJ
SJO-AUA
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 José to Caribbean Islands
SJO-zzEPX
SJO-SDQ
SJO-SJU
SJO-CUR
SJO-PUJ
What is the cheapest month to book a flight from San José to Caribbean Islands?
Currently, June is the cheapest month in which you can book a flight from San José to Caribbean Islands (average of $324). Flying from San José to Caribbean Islands in July is currently the most expensive (average of $479). 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 SJO to EPX?
Find hourly flight availability from San José 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 May 31, 2026.
When flying from San José 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.
How far ahead should I book a flight from San José to Caribbean Islands?
The best time to book flights from San José to Caribbean Islands is 82 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 May 31, 2026.
See what other customers who have flown with Copa Airlines,American Airlines, andAvianca from San José to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.9
Boarding
7.8
Crew
8.1
Overall
7.5
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Boarding
7.8
Crew
8.1
Overall
7.5
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Boarding
7.8
Crew
8.1
Overall
7.5
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Food
6.9
Boarding
7.8
Crew
8.1
Overall
7.5
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
10.0
ExcellentAnonymous,Apr 2026
LIM - PTY
Related info for your journey
Find useful and relevant information for your journey from San José to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for San José to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San José to Caribbean Islands by cabin class
Find flights from San José to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San José and Caribbean Islands flights
Browse other San José and Caribbean Islands flight options. Last updated on May 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San José to Caribbean Islands flights
Consider these flights traveling from San José to Caribbean Islands.
Top 4 airlines flying from San José to Caribbean Islands
Discover the top 4 airlines that operate flights from San José 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 May 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$283 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$170 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$173 | Average$480 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$560 | Average$900 | FlexibilityNo cancel fee | On-time71% |