$119+ Cheap flights from Cleveland (CLE) 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 8/11. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jul 15 — Jul 221
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Caribbean Islands with Cheapflights
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Cheapest flights from Cleveland to Caribbean IslandsExplore the most affordable flight options available from Cleveland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
Explore the most affordable flight options available from Cleveland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:00 pm
CLE
- SJU
1 stop6h 50m
Southwest
Thu 8/273:20 pm
SJU
- CLE
1 stop6h 35m
Southwest
Deal found 6/10![Southwest logo]()
$238
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 8/126:00 am
CLE
- SJU
1 stop16h 24m
American Airlines
Wed 8/195:10 pm
SJU
- CLE
1 stop6h 40m
American Airlines
Deal found 6/12![American Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/222:59 pm
CLE
- SJU
1 stop24h 59m
Frontier
Fri 8/286:41 pm
SJU
- CLE
1 stop28h 31m
Frontier
Deal found 6/10![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/13. 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.
Thu 8/64:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Thu 8/136:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/13![Frontier logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/222:59 pm
CLE
- SJU
1 stop24h 59m
Frontier
Sat 8/296:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/267:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Sat 8/296:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$268
This United Airlines deal was found by Cheapflights users on 6/11. 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 9/186:00 am
CLE
- SJU
1 stop6h 54m
United Airlines
Sat 9/191:00 am
SJU
- CLE
2 stops12h 09m
United Airlines
Deal found 6/11![United Airlines logo]()
$272
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Mon 8/107:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Thu 8/136:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/11![Frontier logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 8/257:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Sat 8/296:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/14![Frontier logo]()
$275
This United Airlines deal was found by Cheapflights users on 6/11. 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 8/218:23 am
CLE
- SJU
2 stops12h 15m
United Airlines
Fri 8/283:56 pm
SJU
- CLE
1 stop8h 02m
United Airlines
Deal found 6/11![United Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/267:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Thu 8/276:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/227:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Sun 8/306:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$285
Best flights from Cleveland to Caribbean IslandsDiscover carefully curated flight deals from Cleveland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
Discover carefully curated flight deals from Cleveland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 15, 2026.
This United Airlines deal was found by Cheapflights users on 6/10. 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 10/25:10 pm
CLE
- SJU
1 stop6h 40m
United Airlines
Tue 10/61:25 pm
SJU
- CLE
1 stop8h 34m
United Airlines
Deal found 6/10![United Airlines logo]()
$238
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/293:00 pm
CLE
- SJU
1 stop8h 56m
Delta
Fri 11/137:15 am
SJU
- CLE
1 stop10h 52m
Delta
Deal found 6/13![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/811:30 am
CLE
- SJU
1 stop13h 05m
Southwest
Mon 10/125:20 pm
SJU
- CLE
1 stop6h 50m
Southwest
Deal found 6/13![Southwest logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/124:32 pm
CLE
- NAS
2 stops17h 10m
American Airlines
Wed 9/162:34 pm
NAS
- CLE
1 stop9h 12m
American Airlines
Deal found 6/10![American Airlines logo]()
$376
This Air Canada deal was found by Cheapflights users on 6/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:10 pm
CLE
- BGI
1 stop19h 25m
Air Canada
Tue 11/104:10 pm
BGI
- CLE
1 stop26h 21m
Air Canada
Deal found 6/11![Air Canada logo]()
$464
This JetBlue deal was found by Cheapflights users on 6/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:25 am
CLE
- NAS
1 stop9h 39m
JetBlue
Wed 8/125:24 pm
NAS
- CLE
1 stop6h 35m
JetBlue
Deal found 6/13![JetBlue logo]()
$471
This Frontier deal was found by Cheapflights users on 6/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/64:05 pm
CLE
- SDQ
2 stops18h 58m
Frontier
Sun 8/912:55 pm
SDQ
- CLE
1 stop11h 46m
Frontier
Deal found 6/13![Frontier logo]()
$473
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 8/14:28 pm
CLE
- NAS
1 stop18h 32m
Multiple Airlines
Thu 8/65:30 pm
NAS
- CLE
1 stop6h 08m
Multiple Airlines
Deal found 6/14![Multiple Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 6/10. 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 9/57:00 am
CLE
- SJU
1 stop7h 44m
United Airlines
Sat 9/121:00 am
SJU
- CLE
2 stops10h 27m
United Airlines
Deal found 6/10![United Airlines logo]()
$292
This Copa Airlines deal was found by Cheapflights users on 6/13. 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 10/810:41 am
CLE
- PUJ
2 stops24h 07m
Copa Airlines
Tue 10/131:36 pm
PUJ
- CLE
2 stops20h 04m
Copa Airlines
Deal found 6/13![Copa Airlines logo]()
$645
This Southwest deal was found by Cheapflights users on 6/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/57:15 am
CLE
- SJU
2 stops10h 50m
Southwest
Sun 9/135:00 am
SJU
- CLE
2 stops9h 25m
Southwest
Deal found 6/10![Southwest logo]()
$374
This United Airlines deal was found by Cheapflights users on 6/14. 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 6/3010:53 am
CLE
- SJU
1 stop9h 41m
United Airlines
Fri 7/32:05 am
SJU
- CLE
1 stop9h 09m
United Airlines
Deal found 6/14![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:10 am
CLE
- MBJ
1 stop5h 59m
Delta
Fri 10/22:35 pm
MBJ
- CLE
1 stop9h 08m
Delta
Deal found 6/13![Delta logo]()
$382
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sun 11/86:00 am
CLE
- SJU
1 stop6h 17m
United Airlines
Tue 11/102:05 am
SJU
- CLE
2 stops12h 07m
United Airlines
Deal found 6/13![United Airlines logo]()
$346
This Southwest deal was found by Cheapflights users on 6/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:15 pm
CLE
- SJU
2 stops10h 30m
Southwest
Wed 11/412:35 pm
SJU
- CLE
2 stops10h 00m
Southwest
Deal found 6/14![Southwest logo]()
$381
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:10 am
CLE
- MBJ
1 stop8h 24m
Delta
Sat 10/312:50 pm
MBJ
- CLE
1 stop9h 12m
Delta
Deal found 6/13![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/59:14 pm
CLE
- STT
2 stops17h 48m
American Airlines
Mon 9/74:42 pm
STT
- CLE
2 stops19h 15m
American Airlines
Deal found 6/10![American Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 6/12. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:45 am
CLE
- SJU
2 stops9h 25m
Southwest
Wed 8/2610:30 am
SJU
- CLE
2 stops10h 30m
Southwest
Deal found 6/12![Southwest logo]()
$386
This JetBlue deal was found by Cheapflights users on 6/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/226:25 am
CLE
- NAS
1 stop9h 50m
JetBlue
Wed 7/295:54 pm
NAS
- CLE
1 stop7h 05m
JetBlue
Deal found 6/13![JetBlue logo]()
$471
This Air Canada deal was found by Cheapflights users on 6/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1010:00 am
CLE
- MBJ
1 stop26h 20m
Air Canada
Sun 9/1312:30 pm
MBJ
- CLE
1 stop24h 37m
Air Canada
Deal found 6/14![Air Canada logo]()
$472
This CheapOair deal was found by Cheapflights users on 6/14. 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 8/53:46 pm
CLE
- SDQ
2 stops19h 17m
Frontier
Sun 8/912:55 pm
SDQ
- CLE
1 stop11h 46m
Frontier
Deal found 6/14![Frontier logo]()
$514
This Southwest deal was found by Cheapflights users on 6/13. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:15 am
CLE
- SJU
2 stops10h 15m
Southwest
Tue 11/310:45 am
SJU
- CLE
2 stops8h 35m
Southwest
Deal found 6/13![Southwest logo]()
$395
This Air Canada deal was found by Cheapflights users on 6/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:00 pm
CLE
- BGI
1 stop20h 25m
Air Canada
Wed 10/74:20 pm
BGI
- CLE
1 stop21h 47m
Air Canada
Deal found 6/12![Air Canada logo]()
$478
This American Airlines deal was found by Cheapflights users on 6/10. 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 9/59:14 pm
CLE
- STT
2 stops18h 38m
American Airlines
Sat 9/124:53 pm
STT
- CLE
2 stops18h 21m
American Airlines
Deal found 6/10![American Airlines logo]()
$482
This JetBlue deal was found by Cheapflights users on 6/13. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:25 am
CLE
- NAS
1 stop9h 39m
JetBlue
Tue 7/146:27 pm
NAS
- CLE
1 stop5h 28m
JetBlue
Deal found 6/13![JetBlue logo]()
$486
This United Airlines deal was found by Cheapflights users on 6/11. 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.
Sun 8/26:24 am
CLE
- NAS
1 stop7h 23m
United Airlines
Fri 8/73:59 pm
NAS
- CLE
1 stop6h 30m
United Airlines
Deal found 6/11![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/58:09 am
CLE
- STT
1 stop6h 53m
Delta
Tue 9/83:02 pm
STT
- CLE
1 stop9h 34m
Delta
Deal found 6/13![Delta logo]()
$476
This American Airlines deal was found by Cheapflights users on 6/14. 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.
Thu 9/107:38 pm
CLE
- MBJ
2 stops16h 24m
American Airlines
Sun 9/1312:05 pm
MBJ
- CLE
1 stop10h 40m
American Airlines
Deal found 6/14![American Airlines logo]()
$488
This Frontier deal was found by Cheapflights users on 6/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:37 am
CLE
- PUJ
1 stop8h 09m
Frontier
Tue 7/711:50 am
PUJ
- CLE
Nonstop4h 30m
Frontier
Deal found 6/14![Frontier logo]()
$537
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:25 am
CLE
- NAS
1 stop9h 39m
JetBlue
Wed 7/151:30 pm
NAS
- CLE
1 stop11h 29m
JetBlue
Deal found 6/11![JetBlue logo]()
$491
Last-minute flights from Cleveland to Caribbean IslandsDiscover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated June 15, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated June 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Sun 6/214:36 pm
CLE
- SJU
1 stop7h 39m
Frontier
Thu 6/256:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/14![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/44:36 pm
CLE
- SJU
1 stop7h 39m
Frontier
Tue 7/76:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/14![Frontier logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 7/47:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Thu 7/96:00 am
SJU
- CLE
1 stop16h 57m
Frontier
Deal found 6/12![Frontier logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 6/14. 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 7/72:48 pm
CLE
- SJU
1 stop11h 27m
Frontier
Thu 7/96:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/14![Frontier logo]()
$323
This eDestinos deal was found by Cheapflights users on 6/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/136:00 am
CLE
- SJU
1 stop29h 16m
Frontier
Mon 7/205:22 pm
SJU
- CLE
1 stop7h 05m
Frontier
Deal found 6/13![Frontier logo]()
$333
This eDestinos deal was found by Cheapflights users on 6/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/156:30 am
CLE
- SJU
1 stop18h 11m
Frontier
Thu 7/236:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/15![Frontier logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Fri 7/174:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Tue 7/216:00 am
SJU
- CLE
1 stop16h 57m
Frontier
Deal found 6/12![Frontier logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Sun 7/196:40 am
CLE
- SJU
2 stops31h 15m
Frontier
Thu 7/307:30 am
SJU
- CLE
1 stop16h 08m
Frontier
Deal found 6/12![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 6/11. 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.
Sun 7/196:40 am
CLE
- SJU
2 stops31h 15m
Frontier
Thu 7/236:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/11![Frontier logo]()
$331
This Kiwi.com deal was found by Cheapflights users on 6/14. 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.
Mon 7/206:40 am
CLE
- SJU
2 stops31h 15m
Frontier
Thu 7/306:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/14![Frontier logo]()
$319
This Kiwi.com deal was found by Cheapflights users on 6/11. 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 7/217:45 am
CLE
- SJU
1 stop8h 20m
Frontier
Wed 7/296:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/11![Frontier logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Fri 7/244:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Thu 7/307:30 am
SJU
- CLE
1 stop16h 08m
Frontier
Deal found 6/12![Frontier logo]()
$324
One-way flights from Cleveland to Caribbean IslandsSearch for one-way flight options from Cleveland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
Search for one-way flight options from Cleveland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 15, 2026.
This Southwest deal was found by Cheapflights users on 6/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1111:40 am
CLE
- SJU
1 stop10h 20m
Southwest
Deal found 6/11![Southwest logo]()
$119
This American Airlines deal was found by Cheapflights users on 6/12. 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.
Wed 8/1212:16 pm
CLE
- SJU
1 stop10h 08m
American Airlines
Deal found 6/12![American Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/117:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Deal found 6/12![Frontier logo]()
$138
This Trip.com deal was found by Cheapflights users on 6/14. 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.
Fri 8/144:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Deal found 6/14![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 6/12. 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 8/47:45 am
CLE
- SJU
1 stop8h 20m
Frontier
Deal found 6/12![Frontier logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 6/12. 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.
Mon 8/34:05 pm
CLE
- SJU
1 stop24h 00m
Frontier
Deal found 6/12![Frontier logo]()
$146
This eDestinos deal was found by Cheapflights users on 6/12. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/72:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Deal found 6/12![Frontier logo]()
$150
This American Airlines deal was found by Cheapflights users on 6/10. 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 10/47:38 pm
CLE
- MBJ
2 stops16h 22m
American Airlines
Deal found 6/10![American Airlines logo]()
$158
This eDestinos deal was found by Cheapflights users on 6/11. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/112:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Deal found 6/11![Frontier logo]()
$162
This Delta deal was found by Cheapflights users on 6/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/48:10 am
CLE
- MBJ
1 stop8h 24m
Delta
Deal found 6/10![Delta logo]()
$162
This United Airlines deal was found by Cheapflights users on 6/10. 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 8/76:41 pm
CLE
- SJU
1 stop10h 48m
United Airlines
Deal found 6/10![United Airlines logo]()
$164
This eDestinos deal was found by Cheapflights users on 6/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/134:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Deal found 6/13![Frontier logo]()
$167
Find flight deals from Cleveland to Caribbean Islands
Keep the following information in mind while searching for Cleveland to Caribbean Islands flight deals. Data was last updated June 15, 2026.
Round-trip from | $238 (Southwest) |
|---|---|
One-way from | $119 (Southwest) |
Popular in | December |
Cheapest in | May |
Average price | $391 |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland 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 June 15, 2026.
Use the filters below to find and compare flights from Cleveland to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 10/2
5:10 pm-11:50 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Tue 10/6
1:25 pm-9:59 pm
1 stop8h 34m
$238
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 9/5
7:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-11:27 am
2 stops10h 27m
$292
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Thu 10/29
3:00 pm-11:56 pm
1 stop8h 56m
San Juan Luis Munoz Marin Intl
Fri 11/13
7:15 am-5:07 pm
1 stop10h 52m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Thu 10/8
11:30 am-12:35 am
1 stop13h 05m
San Juan Luis Munoz Marin Intl
Mon 10/12
5:20 pm-12:10 am
1 stop6h 50m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Tue 6/30
10:53 am-8:34 pm
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Fri 7/3
2:05 am-11:14 am
1 stop9h 09m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 11/8
6:00 am-1:17 pm
1 stop6h 17m
San Juan Luis Munoz Marin Intl
Tue 11/10
2:05 am-1:12 pm
2 stops12h 07m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 9/5
7:15 am-6:05 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Sun 9/13
5:00 am-2:25 pm
2 stops9h 25m
$374
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Sat 9/12
4:32 pm-9:42 am
2 stops17h 10m
Nassau Intl
Wed 9/16
2:34 pm-11:46 pm
1 stop9h 12m
$376
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 10/28
1:15 pm-11:45 pm
2 stops10h 30m
San Juan Luis Munoz Marin Intl
Wed 11/4
12:35 pm-9:35 pm
2 stops10h 00m
$381
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Sun 9/27
8:10 am-1:09 pm
1 stop5h 59m
Montego Bay Sangster Intl
Fri 10/2
2:35 pm-12:43 am
1 stop9h 08m
$382
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Cleveland to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Cleveland with our price prediction graph.
CLE-SJU
CLE-MBJ
CLE-NAS
CLE-BGI
CLE-SDQ
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 Cleveland to Caribbean Islands
CLE-zzEPX
CLE-SJU
CLE-MBJ
CLE-NAS
CLE-BGI
What is the cheapest month to book a flight from Cleveland to Caribbean Islands?
Currently, November is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $145). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $2,395). 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 CLE to EPX?
Find hourly flight availability from Cleveland 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 June 15, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 67% on flights from Cleveland to Caribbean Islands by exploring options for tickets in the afternoon.
How far ahead should I book a flight from Cleveland to Caribbean Islands?
The best time to book flights from Cleveland to Caribbean Islands is 15 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 June 15, 2026.
Read reviews from past customers who have flown Delta,United Airlines, andAmerican Airlines from Cleveland to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.9
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Cleveland 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 Cleveland 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 Cleveland to Caribbean Islands by cabin class
Find flights from Cleveland to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cleveland and Caribbean Islands flights
Browse other Cleveland and Caribbean Islands flight options. Last updated on June 15, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Cleveland to Caribbean Islands flights
Consider these flights traveling from Cleveland to Caribbean Islands.
Top 7 airlines flying from Cleveland to Caribbean Islands
Discover the top 7 airlines that operate flights from Cleveland 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 June 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$123 | Average$519 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$388 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$160 | Average$543 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$181 | Average$445 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$608 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$610 | FlexibilityNo cancel fee | On-time63% |