$110+ 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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJO — SJU
Mar 9 — Mar 161
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 February 7, 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 February 7, 2026.
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Tue 4/287:55 am
SJO
- SJU
1 stop10h 43m
United Airlines
Tue 5/51:00 am
SJU
- SJO
1 stop12h 38m
United Airlines
Deal found 2/4![United Airlines logo]()
$183
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/64:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Mon 3/164:45 pm
SJU
- SJO
1 stop6h 55m
Avianca
Deal found 2/5![Avianca logo]()
$185
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Sat 3/141:00 pm
SJU
- SJO
1 stop13h 15m
Avianca
Deal found 2/5![Avianca logo]()
$187
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/81:50 am
SJO
- SJU
1 stop7h 35m
Avianca
Mon 4/136:35 pm
SJU
- SJO
1 stop7h 20m
Avianca
Deal found 2/6![Avianca logo]()
$196
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/121:40 am
SJO
- SJU
1 stop13h 30m
Avianca
Thu 4/166:35 pm
SJU
- SJO
1 stop7h 20m
Avianca
Deal found 2/5![Avianca logo]()
$198
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/71:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Sun 3/156:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/6![Avianca logo]()
$209
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/221:50 am
SJO
- SJU
1 stop13h 20m
Avianca
Sun 4/266:35 pm
SJU
- SJO
1 stop16h 15m
Avianca
Deal found 2/6![Avianca logo]()
$220
This FlightHub deal was found by Cheapflights users on 2/6. 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.
Fri 2/204:20 pm
SJO
- SJU
1 stop21h 00m
Avianca
Wed 3/46:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/6![Avianca logo]()
$225
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Tue 3/106:30 pm
SJU
- SJO
1 stop16h 20m
Avianca
Deal found 2/3![Avianca logo]()
$233
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Sun 3/16:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/3![Avianca logo]()
$234
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:45 am
SJO
- SJU
1 stop7h 50m
Avianca
Sun 3/14:45 pm
SJU
- SJO
1 stop6h 55m
Avianca
Deal found 2/3![Avianca logo]()
$235
This FlightHub deal was found by Cheapflights users on 2/5. 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.
Thu 3/194:20 pm
SJO
- SJU
1 stop21h 00m
Avianca
Tue 3/241:00 pm
SJU
- SJO
1 stop13h 15m
Avianca
Deal found 2/5![Avianca logo]()
$236
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 February 7, 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 February 7, 2026.
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Sat 3/141:00 pm
SJU
- SJO
1 stop13h 15m
Avianca
Deal found 2/5![Avianca logo]()
$187
This FlightHub deal was found by Cheapflights users on 2/5. 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.
Mon 4/1311:38 am
SJO
- SJU
1 stop8h 21m
Spirit Airlines
Sun 4/199:49 pm
SJU
- SJO
1 stop15h 33m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$254
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 3/411:01 am
SJO
- SDQ
1 stop9h 39m
Copa Airlines
Wed 3/1111:56 am
SDQ
- SJO
1 stop11h 50m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$259
This Arajet deal was found by Cheapflights users on 2/4. 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 4/811:23 am
SJO
- SDQ
Nonstop3h 04m
Arajet
Sat 4/116:00 pm
SDQ
- SJO
Nonstop3h 03m
Arajet
Deal found 2/4![Arajet logo]()
$277
This Arajet deal was found by Cheapflights users on 2/4. 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 2/2511:23 am
SJO
- PUJ
1 stop6h 32m
Multiple Airlines
Tue 3/311:10 am
PUJ
- SJO
1 stop9h 53m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$365
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Thu 3/126:30 pm
SJU
- SJO
1 stop16h 20m
Avianca
Deal found 2/5![Avianca logo]()
$235
This Priceline deal was found by Cheapflights users on 2/6. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/161:05 pm
SJO
- STI
1 stop16h 55m
JetBlue
Wed 5/208:31 am
STI
- SJO
1 stop25h 22m
JetBlue
Deal found 2/6![JetBlue logo]()
$487
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Mon 2/96:00 am
SJO
- MBJ
1 stop31h 12m
American Airlines
Wed 2/111:58 pm
MBJ
- SJO
1 stop25h 17m
American Airlines
Deal found 2/5![American Airlines logo]()
$489
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:00 pm
SJO
- SJU
1 stop17h 25m
Avianca
Sun 4/196:35 pm
SJU
- SJO
1 stop7h 20m
Avianca
Deal found 2/6![Avianca logo]()
$236
This Copa Airlines deal was found by Cheapflights users on 2/3. 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 2/1910:08 am
SJO
- SJU
1 stop10h 24m
Copa Airlines
Wed 2/256:14 pm
SJU
- SJO
1 stop16h 07m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$263
This Copa Airlines deal was found by Cheapflights users on 2/2. 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 2/282:54 pm
SJO
- SJU
1 stop5h 38m
Copa Airlines
Mon 3/26:14 pm
SJU
- SJO
1 stop14h 51m
Copa Airlines
Deal found 2/2![Copa Airlines logo]()
$263
This Copa Airlines deal was found by Cheapflights users on 2/3. 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 3/108:48 am
SJO
- SJU
1 stop5h 21m
Copa Airlines
Thu 3/196:14 pm
SJU
- SJO
3 stops24h 32m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$268
This Copa Airlines deal was found by Cheapflights users on 2/3. 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 3/510:08 am
SJO
- SJU
1 stop10h 21m
Copa Airlines
Fri 3/135:37 am
SJU
- SJO
2 stops13h 09m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$268
This Trip.com deal was found by Cheapflights users on 2/4. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:23 am
SJO
- CUR
2 stops7h 42m
Multiple Airlines
Wed 4/226:15 pm
CUR
- SJO
1 stop7h 40m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$386
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 2/2610:08 am
SJO
- SJU
1 stop10h 24m
Copa Airlines
Thu 3/55:37 am
SJU
- SJO
2 stops13h 09m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$268
This Copa Airlines deal was found by Cheapflights users on 2/5. 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 3/105:50 am
SJO
- SJU
1 stop8h 19m
Copa Airlines
Sun 3/156:14 pm
SJU
- SJO
3 stops24h 32m
Copa Airlines
Deal found 2/5![Copa Airlines logo]()
$268
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/64:15 pm
SJO
- CUR
1 stop17h 10m
Avianca
Sat 3/146:15 pm
CUR
- SJO
1 stop8h 00m
Avianca
Deal found 2/6![Avianca logo]()
$371
This Arajet deal was found by Cheapflights users on 2/3. 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 4/811:23 am
SJO
- PUJ
1 stop6h 32m
Multiple Airlines
Tue 4/142:05 am
PUJ
- SJO
1 stop10h 33m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$424
This Copa Airlines deal was found by Cheapflights users on 2/5. 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 3/98:48 am
SJO
- SJU
1 stop5h 21m
Copa Airlines
Sun 3/156:14 pm
SJU
- SJO
3 stops24h 32m
Copa Airlines
Deal found 2/5![Copa Airlines logo]()
$268
This Avianca deal was found by Cheapflights users on 2/4. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:15 pm
SJO
- CUR
1 stop17h 10m
Avianca
Sun 3/16:15 pm
CUR
- SJO
1 stop16h 35m
Avianca
Deal found 2/4![Avianca logo]()
$371
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Tue 2/106:00 am
SJO
- MBJ
1 stop7h 12m
American Airlines
Thu 2/1211:07 am
MBJ
- SJO
1 stop10h 26m
American Airlines
Deal found 2/5![American Airlines logo]()
$506
This Copa Airlines deal was found by Cheapflights users on 2/3. 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 4/288:13 am
SJO
- SDQ
1 stop12h 38m
Copa Airlines
Wed 5/68:45 am
SDQ
- SJO
1 stop12h 16m
Copa Airlines
Deal found 2/3![Copa Airlines logo]()
$270
This CheapOair deal was found by Cheapflights users on 2/5. 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.
Wed 2/1812:35 pm
SJO
- MBJ
2 stops46h 27m
Spirit Airlines
Tue 2/241:00 pm
MBJ
- SJO
2 stops23h 40m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$549
This Avianca deal was found by Cheapflights users on 2/2. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/194:15 pm
SJO
- CUR
1 stop17h 10m
Avianca
Wed 2/2512:35 pm
CUR
- SJO
1 stop13h 40m
Avianca
Deal found 2/2![Avianca logo]()
$380
This American Airlines deal was found by Cheapflights users on 2/5. 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.
Tue 4/216:30 am
SJO
- MBJ
1 stop8h 07m
American Airlines
Wed 4/2912:56 pm
MBJ
- SJO
1 stop7h 11m
American Airlines
Deal found 2/5![American Airlines logo]()
$517
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 5/1310:05 am
SJO
- SDQ
1 stop14h 20m
Copa Airlines
Wed 5/272:14 pm
SDQ
- SJO
1 stop6h 12m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$270
This CheapOair deal was found by Cheapflights users on 2/5. 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.
Fri 3/1311:38 am
SJO
- MBJ
2 stops46h 27m
Spirit Airlines
Wed 3/1812:00 pm
MBJ
- SJO
2 stops23h 42m
Spirit Airlines
Deal found 2/5![Spirit Airlines logo]()
$558
This Avianca deal was found by Cheapflights users on 2/4. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/181:40 am
SJO
- CUR
1 stop6h 40m
Avianca
Sat 4/2511:35 am
CUR
- SJO
1 stop14h 20m
Avianca
Deal found 2/4![Avianca logo]()
$382
This American Airlines deal was found by Cheapflights users on 2/6. 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 4/266:30 am
SJO
- MBJ
1 stop8h 07m
American Airlines
Fri 5/112:56 pm
MBJ
- SJO
1 stop7h 11m
American Airlines
Deal found 2/6![American Airlines logo]()
$522
This Copa Airlines deal was found by Cheapflights users on 2/4. 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 6/1011:02 am
SJO
- SDQ
1 stop13h 23m
Copa Airlines
Wed 6/178:45 am
SDQ
- SJO
1 stop10h 06m
Copa Airlines
Deal found 2/4![Copa Airlines logo]()
$270
Last-minute flights from San José to Caribbean IslandsDiscover last-minute flight deals from San José to Caribbean Islands. Data last updated February 7, 2026 and is based on user searches.
Discover last-minute flight deals from San José to Caribbean Islands. Data last updated February 7, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 2/5. 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.
Sat 2/74:20 pm
SJO
- SJU
1 stop21h 00m
Avianca
Mon 2/164:45 pm
SJU
- SJO
1 stop6h 55m
Avianca
Deal found 2/5![Avianca logo]()
$249
This Avianca deal was found by Cheapflights users on 2/4. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/164:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Fri 2/206:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/4![Avianca logo]()
$251
This FlightHub deal was found by Cheapflights users on 2/5. 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.
Fri 2/204:20 pm
SJO
- SJU
1 stop21h 00m
Avianca
Fri 2/276:30 pm
SJU
- SJO
1 stop22h 50m
Avianca
Deal found 2/5![Avianca logo]()
$225
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/251:45 am
SJO
- SJU
1 stop7h 50m
Avianca
Sun 3/14:45 pm
SJU
- SJO
1 stop6h 55m
Avianca
Deal found 2/3![Avianca logo]()
$235
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/274:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Sun 3/16:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/3![Avianca logo]()
$234
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Fri 3/66:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/3![Avianca logo]()
$233
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/64:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Mon 3/164:45 pm
SJU
- SJO
1 stop6h 55m
Avianca
Deal found 2/5![Avianca logo]()
$185
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/71:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Sun 3/156:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/6![Avianca logo]()
$209
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Sat 3/141:00 pm
SJU
- SJO
1 stop13h 15m
Avianca
Deal found 2/5![Avianca logo]()
$187
This Avianca deal was found by Cheapflights users on 2/4. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/111:45 am
SJO
- SJU
1 stop7h 50m
Avianca
Sun 3/156:30 pm
SJU
- SJO
1 stop7h 45m
Avianca
Deal found 2/4![Avianca logo]()
$247
This FlightHub deal was found by Cheapflights users on 2/6. 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.
Thu 3/194:20 pm
SJO
- SJU
1 stop21h 00m
Avianca
Tue 3/246:30 pm
SJU
- SJO
1 stop16h 20m
Avianca
Deal found 2/6![Avianca logo]()
$236
This FlightHub deal was found by Cheapflights users on 2/3. 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.
Thu 3/1911:38 am
SJO
- SJU
1 stop8h 21m
Spirit Airlines
Tue 3/247:54 pm
SJU
- SJO
1 stop17h 20m
Spirit Airlines
Deal found 2/3![Spirit Airlines logo]()
$245
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 February 7, 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 February 7, 2026.
This United Airlines deal was found by Cheapflights users on 2/4. 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.
Sat 2/148:45 am
SJO
- SJU
1 stop19h 26m
United Airlines
Deal found 2/4![United Airlines logo]()
$110
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/24:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Deal found 2/6![Avianca logo]()
$114
This Avianca deal was found by Cheapflights users on 2/5. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/254:15 pm
SJO
- SJU
1 stop17h 20m
Avianca
Deal found 2/5![Avianca logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 2/7. 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.
Wed 3/411:23 am
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/7![Arajet logo]()
$119
This Avianca deal was found by Cheapflights users on 2/6. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/201:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Deal found 2/6![Avianca logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 2/6. 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.
Wed 2/1811:23 am
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/6![Arajet logo]()
$132
This Booking.com deal was found by Cheapflights users on 2/3. 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 3/107:48 pm
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/3![Arajet logo]()
$138
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/91:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Deal found 2/3![Avianca logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 2/6. 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 2/247:48 pm
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/6![Arajet logo]()
$144
This Mytrip deal was found by Cheapflights users on 2/6. 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.
Wed 3/1811:23 am
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/6![Arajet logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 2/7. 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 3/37:48 pm
SJO
- SDQ
Nonstop2h 57m
Arajet
Deal found 2/7![Arajet logo]()
$150
This Avianca deal was found by Cheapflights users on 2/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/221:45 am
SJO
- SJU
1 stop13h 20m
Avianca
Deal found 2/3![Avianca logo]()
$150
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 February 7, 2026.
Round-trip from | $178 (Avianca) |
|---|---|
One-way from | $110 (United Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $241 |
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 February 7, 2026.
Use the filters below to find and compare flights from San José to Caribbean Islands that are best for you.
Fly from
San José
Fly to
Caribbean Islands
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
Sat 3/14
1:00 pm-12:15 am
1 stop13h 15m
$187
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Thu 3/5
1:45 am-5:05 pm
1 stop13h 20m
San Juan Luis Munoz Marin Intl
Thu 3/12
6:30 pm-8:50 am
1 stop16h 20m
$235
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Mon 4/13
4:00 pm-11:25 am
1 stop17h 25m
San Juan Luis Munoz Marin Intl
Sun 4/19
6:35 pm-11:55 pm
1 stop7h 20m
$236
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Mon 4/13
11:38 am-9:59 pm
1 stop8h 21m
San Juan Luis Munoz Marin Intl
Sun 4/19
9:49 pm-11:22 am
1 stop15h 33m
$254
San JoséSanto Domingo
SJO - SDQ
SJOSDQ
San José Juan Santamaria Intl
Wed 3/4
11:01 am-10:40 pm
1 stop9h 39m
Santo Domingo Las Americas
Wed 3/11
11:56 am-9:46 pm
1 stop11h 50m
$259
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Thu 2/19
10:08 am-10:32 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Wed 2/25
6:14 pm-8:21 am
1 stop16h 07m
$263
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Sat 2/28
2:54 pm-10:32 pm
1 stop5h 38m
San Juan Luis Munoz Marin Intl
Mon 3/2
6:14 pm-7:05 am
1 stop14h 51m
$263
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Tue 3/10
8:48 am-4:09 pm
1 stop5h 21m
San Juan Luis Munoz Marin Intl
Thu 3/19
6:14 pm-4:46 pm
3 stops24h 32m
$268
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Thu 3/5
10:08 am-10:29 pm
1 stop10h 21m
San Juan Luis Munoz Marin Intl
Fri 3/13
5:37 am-4:46 pm
2 stops13h 09m
$268
San JoséSan Juan
SJO - SJU
SJOSJU
San José Juan Santamaria Intl
Thu 2/26
10:08 am-10:32 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Thu 3/5
5:37 am-4:46 pm
2 stops13h 09m
$268
Showing 1-10 of 60 results
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-SJU
SJO-SDQ
SJO-PUJ
SJO-STI
SJO-MBJ
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-SJU
SJO-SDQ
SJO-PUJ
SJO-STI
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 $115). Flying from San José to Caribbean Islands in December is currently the most expensive (average of $175). 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 February 7, 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.
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 February 7, 2026.
See what other customers who have flown with Copa Airlines, American Airlines, and Avianca 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.
Boarding
7.8
Food
6.8
Overall
7.5
Crew
8.1
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreJuan,Dec 2025
EZE - PTY
Boarding
7.8
Food
6.8
Overall
7.5
Crew
8.1
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreJuan,Dec 2025
EZE - PTY
Boarding
7.8
Food
6.8
Overall
7.5
Crew
8.1
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreJuan,Dec 2025
EZE - PTY
Boarding
7.8
Food
6.8
Overall
7.5
Crew
8.1
Comfort
7.4
Entertainment
6.8
Reviews
1 / 20
2.0
MediocreJuan,Dec 2025
EZE - 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.
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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 February 7, 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 5 airlines flying from San José to Caribbean Islands
Discover the top 5 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 February 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$152 | Average$265 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$163 | Average$434 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$165 | Average$376 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$175 | Average$285 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$510 | Average$590 | FlexibilityNo cancel fee | On-time71% |