$131+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Aug 28 — Sep 41
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Caribbean Islands with Cheapflights
1. Tell us where you want to go
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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 July 29, 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 July 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:10 pm
CLE
- SJU
1 stop18h 07m
Frontier
Sat 9/2610:30 am
SJU
- CLE
1 stop28h 00m
Frontier
Deal found 7/28![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/169:10 pm
CLE
- SJU
1 stop16h 24m
Frontier
Sat 9/269:30 am
SJU
- CLE
2 stops35h 22m
Frontier
Deal found 7/26![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:33 pm
CLE
- SJU
1 stop30h 08m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/167:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Thu 8/205:15 pm
SJU
- CLE
2 stops42h 40m
Frontier
Deal found 7/24![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/62:04 pm
CLE
- SJU
1 stop10h 30m
Frontier
Wed 9/98:45 am
SJU
- CLE
1 stop11h 21m
Frontier
Deal found 7/24![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/225:07 pm
CLE
- SJU
1 stop7h 36m
Frontier
Sat 8/295:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/25![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/182:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/215:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/212:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/285:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Sat 9/56:35 am
SJU
- CLE
1 stop8h 25m
Frontier
Deal found 7/28![Frontier logo]()
$286
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/147:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Wed 9/232:35 pm
NAS
- CLE
1 stop7h 16m
United Airlines
Deal found 7/24![United Airlines logo]()
$358
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 July 29, 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 July 29, 2026.
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
CLE
- SJU
1 stop7h 44m
United Airlines
Sat 9/121:00 am
SJU
- CLE
2 stops12h 08m
United Airlines
Deal found 7/25![United Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am
CLE
- NAS
1 stop5h 55m
Delta
Wed 11/254:55 pm
NAS
- CLE
1 stop8h 03m
Delta
Deal found 7/27![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/85:55 am
CLE
- SJU
2 stops10h 05m
Southwest
Thu 11/124:00 pm
SJU
- CLE
2 stops8h 45m
Southwest
Deal found 7/28![Southwest logo]()
$374
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:00 am
CLE
- NAS
2 stops8h 12m
American Airlines
Mon 9/77:45 am
NAS
- CLE
1 stop16h 05m
American Airlines
Deal found 7/28![American Airlines logo]()
$420
This JetBlue deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am
CLE
- SXM
1 stop7h 00m
JetBlue
Thu 9/243:05 pm
SXM
- CLE
1 stop8h 27m
JetBlue
Deal found 7/28![JetBlue logo]()
$427
This Air Canada deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Sun 10/1810:00 am
CLE
- MBJ
1 stop26h 20m
Air Canada
Thu 10/2212:30 pm
MBJ
- CLE
1 stop24h 37m
Air Canada
Deal found 7/24![Air Canada logo]()
$452
This Expedia deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/137:50 am
CLE
- MBJ
1 stop9h 28m
Multiple Airlines
Thu 8/201:32 pm
MBJ
- CLE
1 stop7h 59m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$505
This Copa Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:52 am
CLE
- AUA
2 stops27h 51m
Copa Airlines
Sun 9/137:10 am
AUA
- CLE
2 stops26h 31m
Copa Airlines
Deal found 7/24![Copa Airlines logo]()
$672
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:00 am
CLE
- NAS
1 stop7h 54m
Delta
Tue 10/201:10 pm
NAS
- CLE
1 stop9h 52m
Delta
Deal found 7/27![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/256:40 am
CLE
- SJU
2 stops10h 15m
Southwest
Mon 9/286:30 am
SJU
- CLE
2 stops10h 15m
Southwest
Deal found 7/25![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:53 am
CLE
- NAS
1 stop5h 55m
United Airlines
Sat 11/74:00 pm
NAS
- CLE
1 stop7h 59m
United Airlines
Deal found 7/27![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:15 am
CLE
- NAS
1 stop11h 24m
American Airlines
Tue 9/87:45 am
NAS
- CLE
2 stops8h 19m
American Airlines
Deal found 7/28![American Airlines logo]()
$420
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/46:00 pm
CLE
- SXM
1 stop17h 15m
Delta
Wed 1/131:40 pm
SXM
- CLE
1 stop11h 55m
Delta
Deal found 7/26![Delta logo]()
$384
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:40 am
CLE
- SJU
2 stops10h 15m
Southwest
Fri 9/1810:00 am
SJU
- CLE
2 stops8h 40m
Southwest
Deal found 7/28![Southwest logo]()
$387
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:53 am
CLE
- NAS
1 stop5h 55m
United Airlines
Sun 11/12:55 pm
NAS
- CLE
1 stop5h 52m
United Airlines
Deal found 7/26![United Airlines logo]()
$394
This JetBlue deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:00 am
CLE
- SXM
1 stop7h 00m
JetBlue
Fri 9/253:05 pm
SXM
- CLE
1 stop8h 27m
JetBlue
Deal found 7/28![JetBlue logo]()
$454
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 9/66:35 am
CLE
- SJU
2 stops8h 55m
Southwest
Wed 9/98:20 am
SJU
- CLE
2 stops10h 10m
Southwest
Deal found 7/24![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/276:00 am
CLE
- NAS
1 stop9h 30m
Delta
Wed 12/21:00 pm
NAS
- CLE
1 stop10h 00m
Delta
Deal found 7/25![Delta logo]()
$392
This American Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:28 pm
CLE
- SDQ
1 stop14h 41m
American Airlines
Tue 11/107:00 am
SDQ
- CLE
1 stop11h 35m
American Airlines
Deal found 7/27![American Airlines logo]()
$441
This Air Canada deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:00 pm
CLE
- PUJ
2 stops21h 05m
Air Canada
Thu 10/293:30 pm
PUJ
- CLE
1 stop26h 47m
Air Canada
Deal found 7/28![Air Canada logo]()
$507
This Cheapflightsfares deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:00 am
CLE
- SDQ
1 stop7h 49m
JetBlue
Mon 9/143:59 pm
SDQ
- CLE
1 stop7h 33m
JetBlue
Deal found 7/24![JetBlue logo]()
$461
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:40 am
CLE
- SJU
2 stops10h 15m
Southwest
Sat 9/510:25 am
SJU
- CLE
2 stops10h 00m
Southwest
Deal found 7/28![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:00 am
CLE
- STT
1 stop6h 56m
United Airlines
Tue 11/33:00 pm
STT
- CLE
1 stop7h 44m
United Airlines
Deal found 7/28![United Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 11/276:00 am
CLE
- NAS
1 stop9h 30m
Delta
Thu 12/31:00 pm
NAS
- CLE
2 stops10h 53m
Delta
Deal found 7/25![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 12/86:00 am
CLE
- SDQ
1 stop7h 00m
American Airlines
Tue 12/156:00 am
SDQ
- CLE
2 stops10h 16m
American Airlines
Deal found 7/25![American Airlines logo]()
$441
This JetBlue deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Sun 9/277:00 am
CLE
- SDQ
1 stop7h 49m
JetBlue
Thu 10/13:59 pm
SDQ
- CLE
1 stop7h 33m
JetBlue
Deal found 7/24![JetBlue logo]()
$464
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:50 pm
CLE
- SJU
2 stops8h 30m
Southwest
Sun 11/15:35 am
SJU
- CLE
2 stops8h 20m
Southwest
Deal found 7/28![Southwest logo]()
$392
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/77:12 pm
CLE
- SXM
1 stop17h 38m
United Airlines
Tue 12/152:52 pm
SXM
- CLE
1 stop22h 06m
United Airlines
Deal found 7/26![United Airlines logo]()
$436
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:10 am
CLE
- NAS
1 stop5h 43m
Delta
Mon 9/211:06 pm
NAS
- CLE
1 stop9h 56m
Delta
Deal found 7/27![Delta logo]()
$398
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/106:00 am
CLE
- SXM
1 stop9h 31m
American Airlines
Mon 11/165:33 pm
SXM
- CLE
2 stops19h 41m
American Airlines
Deal found 7/29![American Airlines logo]()
$449
Last-minute flights from Cleveland to Caribbean IslandsDiscover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated July 29, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean Islands. Data last updated July 29, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:33 pm
CLE
- SJU
1 stop30h 08m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/167:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Thu 8/205:15 pm
SJU
- CLE
2 stops42h 40m
Frontier
Deal found 7/24![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Mon 8/248:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$287
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/171:54 pm
CLE
- SJU
1 stop10h 47m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$291
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/182:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/215:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/212:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/285:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 8/225:07 pm
CLE
- SJU
1 stop7h 36m
Frontier
Sat 8/295:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/25![Frontier logo]()
$282
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:26 am
CLE
- NAS
1 stop6h 25m
Delta
Tue 9/13:22 pm
NAS
- CLE
1 stop9h 07m
Delta
Deal found 7/26![Delta logo]()
$372
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Sat 9/56:35 am
SJU
- CLE
1 stop8h 25m
Frontier
Deal found 7/28![Frontier logo]()
$286
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 July 29, 2026.
Search for one-way flight options from Cleveland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated July 29, 2026.
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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.
Wed 9/96:00 am
CLE
- NAS
1 stop5h 51m
Delta
Deal found 7/24![Delta logo]()
$131
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Deal found 7/24![United Airlines logo]()
$132
This Expedia deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/142:45 pm
CLE
- NAS
2 stops26h 45m
Air Canada
Deal found 7/27![Air Canada logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/285:15 pm
CLE
- SJU
2 stops31h 41m
Frontier
Deal found 7/27![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:00 am
CLE
- SJU
1 stop17h 58m
Frontier
Deal found 7/26![Frontier logo]()
$152
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/317:05 am
CLE
- SXM
1 stop6h 48m
Delta
Deal found 7/28![Delta logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:15 pm
CLE
- SJU
2 stops22h 56m
Frontier
Deal found 7/28![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/268:10 am
CLE
- SJU
1 stop29h 24m
Frontier
Deal found 7/25![Frontier logo]()
$154
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” 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 8/256:45 am
CLE
- SJU
2 stops18h 11m
Frontier
Deal found 7/24![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/243:40 pm
CLE
- SJU
2 stops32h 18m
Frontier
Deal found 7/25![Frontier logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:07 am
CLE
- SJU
1 stop13h 50m
Frontier
Deal found 7/26![Frontier logo]()
$158
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” 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 9/177:00 am
CLE
- SJU
2 stops19h 13m
Frontier
Deal found 7/25![Frontier logo]()
$160
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 July 29, 2026.
Round-trip from | $273 (Kiwi.com) |
|---|---|
One-way from | $131 (Delta) |
Popular in | December |
Cheapest in | May |
Average price | $402 |
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 July 29, 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
Wed 9/9
7:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-1:08 pm
2 stops12h 08m
$369
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Tue 11/17
6:00 am-11:55 am
1 stop5h 55m
Nassau Intl
Wed 11/25
4:55 pm-12:58 am
1 stop8h 03m
$372
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Tue 10/13
6:00 am-1:54 pm
1 stop7h 54m
Nassau Intl
Tue 10/20
1:10 pm-11:02 pm
1 stop9h 52m
$372
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 11/8
5:55 am-5:00 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Thu 11/12
4:00 pm-11:45 pm
2 stops8h 45m
$374
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 9/25
6:40 am-4:55 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:30 am-4:45 pm
2 stops10h 15m
$382
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Mon 1/4
6:00 pm-12:15 pm
1 stop17h 15m
Simpson Bay Princess Juliana
Wed 1/13
1:40 pm-12:35 am
1 stop11h 55m
$384
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 9/14
6:40 am-4:55 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Fri 9/18
10:00 am-6:40 pm
2 stops8h 40m
$387
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 9/6
6:35 am-3:30 pm
2 stops8h 55m
San Juan Luis Munoz Marin Intl
Wed 9/9
8:20 am-6:30 pm
2 stops10h 10m
$387
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Fri 11/27
6:00 am-3:30 pm
1 stop9h 30m
Nassau Intl
Wed 12/2
1:00 pm-11:00 pm
1 stop10h 00m
$392
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 8/31
6:40 am-4:55 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Sat 9/5
10:25 am-8:25 pm
2 stops10h 00m
$392
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-NAS
CLE-SJU
CLE-AUA
CLE-PUJ
CLE-SXM
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-NAS
CLE-SJU
CLE-AUA
CLE-PUJ
What is the cheapest month to book a flight from Cleveland to Caribbean Islands?
Currently, October is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $551). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $703). 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 July 29, 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 33 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 July 29, 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.
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Overall
7.8
Boarding
8.1
Food
7.2
Entertainment
7.8
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 July 29, 2026.
Popular flight searches
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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 July 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$542 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$389 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$184 | Average$578 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$473 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$611 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$228 | Average$540 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$259 | Average$614 | FlexibilityNo cancel fee | On-time63% |