$96+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
May 22 — May 291
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 April 22, 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 April 22, 2026.
This Super.com deal was found by Cheapflights users on 4/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:55 pm
CLE
- SJU
1 stop11h 02m
Frontier
Wed 5/206:41 pm
SJU
- CLE
1 stop29h 54m
Frontier
Deal found 4/17![Frontier logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Tue 6/24:46 pm
SJU
- CLE
1 stop6h 58m
Frontier
Deal found 4/18![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Sun 5/319:00 am
SJU
- CLE
1 stop10h 29m
Frontier
Deal found 4/18![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/66:33 pm
CLE
- SJU
1 stop29h 24m
Frontier
Sun 5/106:00 am
SJU
- CLE
1 stop17h 12m
Frontier
Deal found 4/20![Frontier logo]()
$203
This CheapOair deal was found by Cheapflights users on 4/18. 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 5/237:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sun 5/316:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/18![Frontier logo]()
$204
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Tue 6/166:00 am
SJU
- CLE
1 stop16h 54m
Frontier
Deal found 4/20![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 4/20. 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.
Fri 6/59:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Sat 6/63:58 pm
SJU
- CLE
1 stop7h 51m
Frontier
Deal found 4/20![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 6/42:29 pm
CLE
- SJU
1 stop11h 39m
Frontier
Tue 6/96:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 4/21![Frontier logo]()
$210
This eDestinos deal was found by Cheapflights users on 4/17. 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 4/274:28 pm
CLE
- SJU
1 stop7h 15m
Frontier
Mon 5/411:07 am
SJU
- CLE
1 stop9h 48m
Frontier
Deal found 4/17![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 4/17. 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.
Mon 6/17:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sat 6/68:13 pm
SJU
- CLE
1 stop11h 35m
Frontier
Deal found 4/17![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Mon 6/16:41 pm
SJU
- CLE
1 stop28h 18m
Frontier
Deal found 4/18![Frontier logo]()
$213
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:40 am
CLE
- PUJ
1 stop7h 45m
Frontier
Mon 8/1011:42 am
PUJ
- CLE
1 stop11h 30m
Frontier
Deal found 4/19![Frontier logo]()
$251
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 April 22, 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 April 22, 2026.
This American Airlines deal was found by Cheapflights users on 4/19. 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 5/46:00 am
CLE
- STT
1 stop8h 49m
American Airlines
Fri 5/82:30 pm
STT
- CLE
1 stop9h 56m
American Airlines
Deal found 4/19![American Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 4/17. 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 6/2812:39 pm
CLE
- SJU
1 stop9h 48m
Delta
Sat 7/45:56 pm
SJU
- CLE
1 stop6h 51m
Delta
Deal found 4/17![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 4/22. 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 5/268:15 am
CLE
- AUA
1 stop8h 25m
United Airlines
Fri 5/291:50 pm
AUA
- CLE
1 stop8h 45m
United Airlines
Deal found 4/22![United Airlines logo]()
$375
This Southwest deal was found by Cheapflights users on 4/19. 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.
Mon 5/412:40 pm
CLE
- SJU
2 stops10h 45m
Southwest
Fri 5/85:05 am
SJU
- CLE
2 stops10h 00m
Southwest
Deal found 4/19![Southwest logo]()
$398
This Expedia deal was found by Cheapflights users on 4/22. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/117:00 pm
CLE
- BGI
1 stop20h 25m
Air Canada
Sun 9/204:20 pm
BGI
- CLE
1 stop21h 47m
Air Canada
Deal found 4/22![Air Canada logo]()
$408
This CheapOair deal was found by Cheapflights users on 4/18. 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 6/255:51 pm
CLE
- MBJ
1 stop19h 30m
Multiple Airlines
Mon 6/2912:30 pm
MBJ
- CLE
1 stop24h 35m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$422
This CheapOair deal was found by Cheapflights users on 4/19. 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.
Mon 6/11:00 pm
CLE
- MBJ
2 stops24h 11m
Frontier
Fri 6/51:16 pm
MBJ
- CLE
2 stops17h 44m
Frontier
Deal found 4/19![Frontier logo]()
$455
This JetBlue deal was found by Cheapflights users on 4/17. 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 5/116:00 am
CLE
- PUJ
1 stop7h 27m
JetBlue
Thu 5/1412:44 pm
PUJ
- CLE
1 stop10h 50m
JetBlue
Deal found 4/17![JetBlue logo]()
$521
This Delta deal was found by Cheapflights users on 4/18. 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 4/251:53 pm
CLE
- SJU
1 stop6h 31m
Delta
Wed 4/297:30 am
SJU
- CLE
1 stop11h 12m
Delta
Deal found 4/18![Delta logo]()
$316
This Copa Airlines deal was found by Cheapflights users on 4/18. 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 7/812:22 pm
CLE
- PUJ
2 stops22h 21m
Copa Airlines
Wed 7/1512:51 pm
PUJ
- CLE
2 stops21h 03m
Copa Airlines
Deal found 4/18![Copa Airlines logo]()
$641
This American Airlines deal was found by Cheapflights users on 4/21. 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 7/67:30 pm
CLE
- MBJ
1 stop19h 00m
American Airlines
Fri 7/102:23 pm
MBJ
- CLE
1 stop17h 49m
American Airlines
Deal found 4/21![American Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 4/18. 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.
Fri 8/146:00 am
CLE
- MBJ
1 stop10h 34m
Delta
Tue 8/184:59 pm
MBJ
- CLE
1 stop6h 37m
Delta
Deal found 4/18![Delta logo]()
$352
This United Airlines deal was found by Cheapflights users on 4/18. 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 5/88:30 am
CLE
- SJU
2 stops12h 54m
United Airlines
Tue 5/127:20 am
SJU
- CLE
2 stops13h 24m
United Airlines
Deal found 4/18![United Airlines logo]()
$406
This Orbitz deal was found by Cheapflights users on 4/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:00 pm
CLE
- BGI
1 stop20h 25m
Air Canada
Tue 10/64:20 pm
BGI
- CLE
1 stop21h 47m
Air Canada
Deal found 4/19![Air Canada logo]()
$408
This Southwest deal was found by Cheapflights users on 4/19. 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 5/95:40 am
CLE
- SJU
2 stops9h 10m
Southwest
Thu 5/145:35 am
SJU
- CLE
2 stops9h 30m
Southwest
Deal found 4/19![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 4/20. 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.
Tue 5/196:00 am
CLE
- AUA
1 stop8h 10m
Delta
Tue 5/263:25 pm
AUA
- CLE
1 stop9h 07m
Delta
Deal found 4/20![Delta logo]()
$375
This United Airlines deal was found by Cheapflights users on 4/17. 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.
Mon 4/272:21 pm
CLE
- SJU
2 stops9h 29m
United Airlines
Fri 5/17:20 am
SJU
- CLE
2 stops11h 06m
United Airlines
Deal found 4/17![United Airlines logo]()
$416
This CheapOair deal was found by Cheapflights users on 4/21. 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.
Sun 7/123:46 pm
CLE
- MBJ
1 stop21h 35m
Frontier
Sun 7/261:26 pm
MBJ
- CLE
2 stops17h 12m
Frontier
Deal found 4/21![Frontier logo]()
$472
This American Airlines deal was found by Cheapflights users on 4/20. 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 5/317:03 pm
CLE
- STT
1 stop17h 41m
American Airlines
Tue 6/24:48 pm
STT
- CLE
1 stop7h 01m
American Airlines
Deal found 4/20![American Airlines logo]()
$433
This Delta deal was found by Cheapflights users on 4/20. 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.
Mon 5/186:00 am
CLE
- AUA
1 stop8h 10m
Delta
Tue 5/263:25 pm
AUA
- CLE
1 stop9h 07m
Delta
Deal found 4/20![Delta logo]()
$375
This Air Canada deal was found by Cheapflights users on 4/20. 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 8/2910:00 am
CLE
- BGI
1 stop29h 25m
Air Canada
Tue 9/14:20 pm
BGI
- CLE
2 stops26h 03m
Air Canada
Deal found 4/20![Air Canada logo]()
$456
This Southwest deal was found by Cheapflights users on 4/18. 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.
Mon 5/1810:55 am
CLE
- NAS
1 stop7h 35m
Southwest
Mon 5/258:45 am
NAS
- CLE
1 stop7h 35m
Southwest
Deal found 4/18![Southwest logo]()
$467
This United Airlines deal was found by Cheapflights users on 4/20. 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 9/266:12 am
CLE
- STT
1 stop9h 31m
United Airlines
Sat 10/34:45 pm
STT
- CLE
1 stop7h 02m
United Airlines
Deal found 4/20![United Airlines logo]()
$425
This JetBlue deal was found by Cheapflights users on 4/20. 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 5/116:00 am
CLE
- SXM
1 stop9h 22m
JetBlue
Thu 5/142:32 pm
SXM
- CLE
1 stop9h 02m
JetBlue
Deal found 4/20![JetBlue logo]()
$539
This Orbitz deal was found by Cheapflights users on 4/19. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/177:00 pm
CLE
- BGI
1 stop20h 25m
Air Canada
Thu 10/224:20 pm
BGI
- CLE
1 stop21h 47m
Air Canada
Deal found 4/19![Air Canada logo]()
$458
This Southwest deal was found by Cheapflights users on 4/22. 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.
Fri 5/2210:55 am
CLE
- NAS
1 stop7h 35m
Southwest
Wed 5/278:45 am
NAS
- CLE
1 stop9h 55m
Southwest
Deal found 4/22![Southwest logo]()
$467
This Expedia deal was found by Cheapflights users on 4/20. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:25 am
CLE
- PLS
1 stop6h 25m
Multiple Airlines
Fri 6/192:45 pm
PLS
- CLE
2 stops23h 20m
Multiple Airlines
Deal found 4/20![Multiple Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 4/21. 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 5/711:01 am
CLE
- SJU
2 stops10h 23m
United Airlines
Thu 5/147:20 am
SJU
- CLE
2 stops15h 00m
United Airlines
Deal found 4/21![United Airlines logo]()
$456
This Expedia deal was found by Cheapflights users on 4/21. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1610:00 am
CLE
- BGI
1 stop29h 25m
Air Canada
Tue 7/214:20 pm
BGI
- CLE
1 stop28h 15m
Air Canada
Deal found 4/21![Air Canada logo]()
$468
This Delta deal was found by Cheapflights users on 4/22. 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.
Tue 7/77:05 am
CLE
- STT
1 stop7h 18m
Delta
Sun 7/121:21 pm
STT
- CLE
1 stop11h 36m
Delta
Deal found 4/22![Delta logo]()
$431
Last-minute flights from Cleveland to Caribbean IslandsDiscover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated April 22, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated April 22, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 4/17. 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 4/274:28 pm
CLE
- SJU
1 stop7h 15m
Frontier
Mon 5/411:07 am
SJU
- CLE
1 stop9h 48m
Frontier
Deal found 4/17![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/66:33 pm
CLE
- SJU
1 stop29h 24m
Frontier
Sun 5/106:00 am
SJU
- CLE
1 stop17h 12m
Frontier
Deal found 4/20![Frontier logo]()
$203
This Frontier deal was found by Cheapflights users on 4/20. 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.
Fri 5/82:14 pm
CLE
- SJU
1 stop8h 29m
Frontier
Mon 5/113:03 am
SJU
- CLE
1 stop10h 06m
Frontier
Deal found 4/20![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/17. 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 5/104:11 pm
CLE
- SJU
1 stop7h 46m
Frontier
Thu 5/147:00 am
SJU
- CLE
2 stops12h 32m
Frontier
Deal found 4/17![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/113:49 pm
CLE
- SJU
2 stops10h 19m
Frontier
Thu 5/147:00 am
SJU
- CLE
1 stop14h 25m
Frontier
Deal found 4/20![Frontier logo]()
$221
This Super.com deal was found by Cheapflights users on 4/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:57 pm
CLE
- SJU
1 stop15h 18m
Frontier
Tue 5/196:41 pm
SJU
- CLE
1 stop28h 19m
Frontier
Deal found 4/17![Frontier logo]()
$200
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Tue 6/166:00 am
SJU
- CLE
1 stop16h 54m
Frontier
Deal found 4/20![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Tue 6/24:46 pm
SJU
- CLE
1 stop6h 58m
Frontier
Deal found 4/18![Frontier logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Sun 5/319:00 am
SJU
- CLE
1 stop10h 29m
Frontier
Deal found 4/18![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/225:18 pm
CLE
- SJU
1 stop27h 22m
Frontier
Mon 6/16:41 pm
SJU
- CLE
1 stop28h 18m
Frontier
Deal found 4/18![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 4/18. 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 5/237:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sun 5/316:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/18![Frontier logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/282:29 pm
CLE
- SJU
1 stop11h 39m
Frontier
Thu 6/43:58 pm
SJU
- CLE
1 stop7h 13m
Frontier
Deal found 4/20![Frontier logo]()
$210
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 April 22, 2026.
Search for one-way flight options from Cleveland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 22, 2026.
This eDestinos deal was found by Cheapflights users on 4/20. 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 5/206:30 am
CLE
- SJU
1 stop16h 13m
Frontier
Deal found 4/20![Frontier logo]()
$96
This Super.com deal was found by Cheapflights users on 4/21. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/74:11 pm
CLE
- SJU
1 stop7h 46m
Frontier
Deal found 4/21![Frontier logo]()
$97
This Frontier deal was found by Cheapflights users on 4/21. 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.
Sat 5/99:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Deal found 4/21![Frontier logo]()
$98
This eDestinos deal was found by Cheapflights users on 4/19. 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 5/271:27 pm
CLE
- SJU
1 stop27h 45m
Frontier
Deal found 4/19![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 4/19. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:33 pm
CLE
- SJU
1 stop29h 24m
Frontier
Deal found 4/19![Frontier logo]()
$102
This Frontier deal was found by Cheapflights users on 4/20. 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.
Fri 5/86:30 am
CLE
- SJU
1 stop10h 44m
Frontier
Deal found 4/20![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 4/19. 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 5/36:15 am
CLE
- SJU
1 stop30h 08m
Frontier
Deal found 4/19![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 4/297:38 pm
CLE
- SJU
1 stop16h 45m
Frontier
Deal found 4/22![Frontier logo]()
$110
This Priceline deal was found by Cheapflights users on 4/20. 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.
Sat 5/308:55 am
CLE
- SJU
1 stop14h 27m
Frontier
Deal found 4/20![Frontier logo]()
$111
This eDestinos deal was found by Cheapflights users on 4/20. 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 5/239:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Deal found 4/20![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/159:57 pm
CLE
- PUJ
1 stop11h 21m
Frontier
Deal found 4/20![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 4/20. 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.
Sun 5/176:54 am
CLE
- PUJ
1 stop7h 30m
Frontier
Deal found 4/20![Frontier logo]()
$114
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 April 22, 2026.
Round-trip from | $200 (eDestinos) |
|---|---|
One-way from | $96 (eDestinos) |
Popular in | December |
Cheapest in | May |
Average price | $303 |
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 April 22, 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
ClevelandSaint Thomas Island
CLE - STT
CLESTT
Cleveland Hopkins Intl
Mon 5/4
6:00 am-2:49 pm
1 stop8h 49m
Saint Thomas Island Cyril E King
Fri 5/8
2:30 pm-12:26 am
1 stop9h 56m
$290
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 6/28
12:39 pm-10:27 pm
1 stop9h 48m
San Juan Luis Munoz Marin Intl
Sat 7/4
5:56 pm-12:47 am
1 stop6h 51m
$316
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 4/25
1:53 pm-8:24 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Wed 4/29
7:30 am-6:42 pm
1 stop11h 12m
$316
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Fri 8/14
6:00 am-3:34 pm
1 stop10h 34m
Montego Bay Sangster Intl
Tue 8/18
4:59 pm-12:36 am
1 stop6h 37m
$352
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Mon 7/6
7:30 pm-1:30 pm
1 stop19h 00m
Montego Bay Sangster Intl
Fri 7/10
2:23 pm-9:12 am
1 stop17h 49m
$359
ClevelandOranjestad
CLE - AUA
CLEAUA
Cleveland Hopkins Intl
Tue 5/26
8:15 am-4:40 pm
1 stop8h 25m
Oranjestad Reina Beatrix
Fri 5/29
1:50 pm-10:35 pm
1 stop8h 45m
$375
ClevelandOranjestad
CLE - AUA
CLEAUA
Cleveland Hopkins Intl
Tue 5/19
6:00 am-2:10 pm
1 stop8h 10m
Oranjestad Reina Beatrix
Tue 5/26
3:25 pm-12:32 am
1 stop9h 07m
$375
ClevelandOranjestad
CLE - AUA
CLEAUA
Cleveland Hopkins Intl
Mon 5/18
6:00 am-2:10 pm
1 stop8h 10m
Oranjestad Reina Beatrix
Tue 5/26
3:25 pm-12:32 am
1 stop9h 07m
$375
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 5/4
12:40 pm-11:25 pm
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Fri 5/8
5:05 am-3:05 pm
2 stops10h 00m
$398
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 5/8
8:30 am-9:24 pm
2 stops12h 54m
San Juan Luis Munoz Marin Intl
Tue 5/12
7:20 am-8:44 pm
2 stops13h 24m
$406
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-STT
CLE-SJU
CLE-AUA
CLE-BGI
CLE-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 Cleveland to Caribbean Islands
CLE-zzEPX
CLE-STT
CLE-SJU
CLE-AUA
CLE-BGI
What is the cheapest month to book a flight from Cleveland to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $119). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $1,617). 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 April 22, 2026.
Unlike at noon, when flights are generally more expensive, you can save up to 70% on flights from Cleveland to Caribbean Islands by exploring options for tickets in the afternoon.
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 April 22, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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 April 22, 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 6 airlines flying from Cleveland to Caribbean Islands
Discover the top 6 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 April 22, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$102 | Average$516 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$160 | Average$540 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$170 | Average$441 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$218 | Average$585 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$544 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$568 | FlexibilityNo cancel fee | On-time63% |