$94+ Cheap flights from Cleveland (CLE) to Caribbean
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 5/23. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
May 28 — Jun 41
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Caribbean with Cheapflights
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Cheapest flights from Cleveland to CaribbeanExplore the most affordable flight options available from Cleveland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
Explore the most affordable flight options available from Cleveland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/176:20 am
CLE
- SJU
1 stop17h 37m
Frontier
Sun 5/246:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/23![Frontier logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Thu 5/144:11 pm
CLE
- SJU
1 stop7h 46m
Frontier
Sun 5/173:33 pm
SJU
- CLE
1 stop7h 39m
Frontier
Deal found 4/26![Frontier logo]()
$202
This eDestinos deal was found by Cheapflights users on 4/24. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/33:48 pm
CLE
- SJU
1 stop25h 38m
Frontier
Wed 6/106:00 am
SJU
- CLE
1 stop16h 54m
Frontier
Deal found 4/24![Frontier logo]()
$203
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier 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 5/193:33 pm
SJU
- CLE
1 stop7h 38m
Frontier
Deal found 4/27![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:45 am
CLE
- SJU
1 stop9h 31m
Frontier
Wed 7/296:31 pm
SJU
- CLE
1 stop13h 25m
Frontier
Deal found 4/27![Frontier logo]()
$206
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
CLE
- SJU
1 stop6h 45m
Frontier
Sun 5/173:33 pm
SJU
- CLE
1 stop7h 39m
Frontier
Deal found 4/26![Frontier logo]()
$207
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/277:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sun 5/314:46 pm
SJU
- CLE
1 stop7h 52m
Frontier
Deal found 4/27![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/245:18 pm
CLE
- SJU
1 stop24h 08m
Frontier
Sun 5/316:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/26![Frontier logo]()
$211
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:30 am
CLE
- SJU
1 stop6h 45m
Frontier
Fri 6/53:12 pm
SJU
- CLE
1 stop9h 23m
Frontier
Deal found 4/27![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 6/22:29 pm
CLE
- SJU
1 stop11h 42m
Frontier
Mon 6/86:30 pm
SJU
- CLE
1 stop13h 27m
Frontier
Deal found 4/24![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/24. 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.
Sat 6/69:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Thu 6/116:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 4/24![Frontier logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/285:18 pm
CLE
- SJU
1 stop24h 08m
Frontier
Sun 5/319:00 am
SJU
- CLE
1 stop10h 29m
Frontier
Deal found 4/27![Frontier logo]()
$219
Best flights from Cleveland to CaribbeanDiscover carefully curated flight deals from Cleveland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
Discover carefully curated flight deals from Cleveland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 28, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/277:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sun 5/316:41 pm
SJU
- CLE
2 stops23h 46m
Frontier
Deal found 4/27![Frontier logo]()
$263
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Sat 5/97:00 am
CLE
- STT
1 stop10h 00m
United Airlines
Wed 5/132:10 pm
STT
- CLE
1 stop8h 34m
United Airlines
Deal found 4/24![United Airlines logo]()
$290
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/27:05 am
CLE
- SJU
1 stop9h 18m
Delta
Wed 5/65:34 pm
SJU
- CLE
1 stop7h 00m
Delta
Deal found 4/23![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 6/305:44 am
CLE
- MBJ
2 stops9h 16m
American Airlines
Tue 7/72:23 pm
MBJ
- CLE
1 stop17h 49m
American Airlines
Deal found 4/23![American Airlines logo]()
$357
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.
Sun 5/103:42 pm
CLE
- AUA
1 stop22h 54m
Multiple Airlines
Mon 6/13:41 pm
AUA
- CLE
1 stop23h 01m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$361
This Expedia deal was found by Cheapflights users on 4/25. 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.
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 4/25![Air Canada logo]()
$388
This Southwest deal was found by Cheapflights users on 4/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3012:55 pm
CLE
- SJU
2 stops10h 30m
Southwest
Wed 5/611:25 am
SJU
- CLE
2 stops10h 10m
Southwest
Deal found 4/26![Southwest logo]()
$509
This JetBlue deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/186:00 am
CLE
- SDQ
1 stop13h 22m
JetBlue
Fri 5/224:14 pm
SDQ
- CLE
1 stop7h 45m
JetBlue
Deal found 4/23![JetBlue logo]()
$614
This Copa Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/1210:37 am
CLE
- PUJ
2 stops15h 34m
Copa Airlines
Fri 6/1912:07 pm
PUJ
- CLE
2 stops21h 38m
Copa Airlines
Deal found 4/27![Copa Airlines logo]()
$679
This Frontier deal was found by Cheapflights users on 4/25. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:24 pm
CLE
- SDQ
2 stops18h 15m
Frontier
Sat 5/302:44 pm
SDQ
- CLE
2 stops17h 04m
Frontier
Deal found 4/25![Frontier logo]()
$371
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:26 am
CLE
- MBJ
1 stop8h 04m
United Airlines
Sat 8/84:33 pm
MBJ
- CLE
1 stop17h 41m
United Airlines
Deal found 4/27![United Airlines logo]()
$373
This Delta deal was found by Cheapflights users on 4/25. 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.
Tue 6/165:35 am
CLE
- SXM
1 stop8h 18m
Delta
Wed 6/243:18 pm
SXM
- CLE
1 stop9h 29m
Delta
Deal found 4/25![Delta logo]()
$385
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/167:29 pm
CLE
- SXM
2 stops17h 11m
American Airlines
Wed 6/242:22 pm
SXM
- CLE
1 stop9h 37m
American Airlines
Deal found 4/22![American Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 6/48:46 pm
CLE
- MBJ
1 stop16h 25m
Multiple Airlines
Tue 6/91:36 pm
MBJ
- CLE
2 stops30h 19m
Multiple Airlines
Deal found 4/23![Multiple Airlines logo]()
$406
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sun 5/316:00 am
CLE
- AUA
1 stop9h 30m
United Airlines
Fri 6/54:30 pm
AUA
- CLE
1 stop7h 14m
United Airlines
Deal found 4/25![United Airlines logo]()
$375
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/277:39 pm
CLE
- SXM
2 stops20h 03m
American Airlines
Thu 7/22:51 pm
SXM
- CLE
1 stop7h 31m
American Airlines
Deal found 4/22![American Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 4/26. 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.
Sat 8/296:00 am
CLE
- STT
1 stop9h 00m
Delta
Sat 9/53:02 pm
STT
- CLE
1 stop6h 52m
Delta
Deal found 4/26![Delta logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 6/115:51 pm
CLE
- MBJ
1 stop19h 30m
Frontier
Thu 6/181:26 pm
MBJ
- CLE
1 stop21h 26m
Frontier
Deal found 4/27![Frontier logo]()
$413
This Air Canada deal was found by Cheapflights users on 4/27. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/172:45 pm
CLE
- BGI
2 stops24h 40m
Air Canada
Thu 10/224:20 pm
BGI
- CLE
2 stops50h 03m
Air Canada
Deal found 4/27![Air Canada logo]()
$455
This United Airlines deal was found by Cheapflights users on 4/26. 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 6/106:00 am
CLE
- SXM
1 stop6h 33m
United Airlines
Wed 6/173:50 pm
SXM
- CLE
1 stop7h 54m
United Airlines
Deal found 4/26![United Airlines logo]()
$385
This Delta deal was found by Cheapflights users on 4/26. 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.
Thu 5/217:42 pm
CLE
- AUA
1 stop16h 18m
Delta
Thu 5/283:25 pm
AUA
- CLE
1 stop17h 52m
Delta
Deal found 4/26![Delta logo]()
$405
This American Airlines deal was found by Cheapflights users on 4/27. 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.
Thu 7/96:01 am
CLE
- AUA
1 stop10h 58m
American Airlines
Wed 7/155:59 pm
AUA
- CLE
2 stops17h 13m
American Airlines
Deal found 4/27![American Airlines logo]()
$410
This CheapOair deal was found by Cheapflights users on 4/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/286:45 am
CLE
- MBJ
1 stop6h 42m
Frontier
Wed 8/121:32 pm
MBJ
- CLE
2 stops32h 25m
Frontier
Deal found 4/27![Frontier logo]()
$417
This United Airlines deal was found by Cheapflights users on 4/26. 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 6/16:00 am
CLE
- SXM
1 stop6h 33m
United Airlines
Fri 6/53:50 pm
SXM
- CLE
1 stop7h 54m
United Airlines
Deal found 4/26![United Airlines logo]()
$385
This Southwest deal was found by Cheapflights users on 4/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:15 pm
CLE
- SJU
2 stops8h 00m
Southwest
Thu 6/115:00 am
SJU
- CLE
2 stops10h 20m
Southwest
Deal found 4/26![Southwest logo]()
$532
This Delta deal was found by Cheapflights users on 4/24. 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.
Fri 8/146:00 am
CLE
- MBJ
1 stop10h 34m
Delta
Tue 8/182:29 pm
MBJ
- CLE
1 stop9h 07m
Delta
Deal found 4/24![Delta logo]()
$413
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 7/17:07 am
CLE
- AUA
2 stops9h 52m
American Airlines
Sun 7/55:59 pm
AUA
- CLE
2 stops17h 13m
American Airlines
Deal found 4/25![American Airlines logo]()
$420
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:05 pm
CLE
- SDQ
2 stops21h 01m
Frontier
Thu 6/1811:55 am
SDQ
- CLE
1 stop8h 28m
Frontier
Deal found 4/27![Frontier logo]()
$436
This Southwest deal was found by Cheapflights users on 4/24. 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.
Mon 5/1812:40 pm
CLE
- SJU
2 stops10h 45m
Southwest
Fri 5/226:50 am
SJU
- CLE
2 stops9h 45m
Southwest
Deal found 4/24![Southwest logo]()
$532
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Tue 6/96:00 am
CLE
- MBJ
1 stop10h 10m
United Airlines
Fri 6/124:12 pm
MBJ
- CLE
1 stop6h 32m
United Airlines
Deal found 4/24![United Airlines logo]()
$405
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated April 28, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated April 28, 2026 and is based on user searches.
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:30 am
CLE
- SJU
1 stop6h 45m
Frontier
Fri 6/53:12 pm
SJU
- CLE
1 stop9h 23m
Frontier
Deal found 4/27![Frontier logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/129:57 pm
CLE
- SJU
1 stop15h 18m
Frontier
Tue 5/263:03 am
SJU
- CLE
1 stop10h 06m
Frontier
Deal found 4/26![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
Thu 5/144:11 pm
CLE
- SJU
1 stop7h 46m
Frontier
Sun 5/173:33 pm
SJU
- CLE
1 stop7h 39m
Frontier
Deal found 4/26![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier 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 5/193:33 pm
SJU
- CLE
1 stop7h 38m
Frontier
Deal found 4/27![Frontier logo]()
$204
This Frontier deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/169:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Sun 5/246:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/23![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/176:20 am
CLE
- SJU
1 stop17h 37m
Frontier
Sun 5/246:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/23![Frontier logo]()
$198
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:30 am
CLE
- SJU
1 stop6h 45m
Frontier
Sun 5/173:33 pm
SJU
- CLE
1 stop7h 39m
Frontier
Deal found 4/26![Frontier logo]()
$207
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:45 am
CLE
- SJU
1 stop9h 31m
Frontier
Wed 7/296:31 pm
SJU
- CLE
1 stop13h 25m
Frontier
Deal found 4/27![Frontier logo]()
$206
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 5/245:18 pm
CLE
- SJU
1 stop24h 08m
Frontier
Sun 5/316:00 am
SJU
- CLE
1 stop8h 42m
Frontier
Deal found 4/26![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Wed 5/277:45 am
CLE
- SJU
1 stop8h 10m
Frontier
Sun 5/314:46 pm
SJU
- CLE
1 stop7h 52m
Frontier
Deal found 4/27![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/285:18 pm
CLE
- SJU
1 stop24h 08m
Frontier
Sun 5/319:00 am
SJU
- CLE
1 stop10h 29m
Frontier
Deal found 4/27![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/27. 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.
Thu 5/285:18 pm
CLE
- SJU
1 stop24h 08m
Frontier
Thu 6/46:09 pm
SJU
- CLE
1 stop13h 39m
Frontier
Deal found 4/27![Frontier logo]()
$220
One-way flights from Cleveland to CaribbeanSearch for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 28, 2026.
This eDestinos deal was found by Cheapflights users on 4/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/231:27 pm
CLE
- SJU
1 stop27h 45m
Frontier
Deal found 4/26![Frontier logo]()
$94
This eDestinos deal was found by Cheapflights users on 4/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/302:29 pm
CLE
- SJU
1 stop8h 53m
Frontier
Deal found 4/25![Frontier logo]()
$96
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier 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
Deal found 4/27![Frontier logo]()
$98
This eDestinos deal was found by Cheapflights users on 4/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/209:57 pm
CLE
- SJU
1 stop25h 25m
Frontier
Deal found 4/26![Frontier logo]()
$101
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:18 pm
CLE
- SJU
1 stop28h 34m
Frontier
Deal found 4/22![Frontier logo]()
$103
This Super.com deal was found by Cheapflights users on 4/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:01 pm
CLE
- SJU
1 stop7h 58m
Frontier
Deal found 4/26![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 4/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/159:57 pm
CLE
- SJU
1 stop10h 07m
Frontier
Deal found 4/27![Frontier logo]()
$106
This eDestinos deal was found by Cheapflights users on 4/25. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Deal found 4/25![Frontier logo]()
$107
This WAYA deal was found by Cheapflights users on 4/26. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:23 am
CLE
- SJU
1 stop7h 36m
Frontier
Deal found 4/26![Frontier logo]()
$110
This Orbitz deal was found by Cheapflights users on 4/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:43 am
CLE
- SJU
1 stop17h 25m
Frontier
Deal found 4/27![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 4/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/245:18 pm
CLE
- PUJ
1 stop17h 17m
Frontier
Deal found 4/26![Frontier logo]()
$113
This Expedia deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Sat 5/163:49 pm
CLE
- PUJ
1 stop22h 35m
Frontier
Deal found 4/23![Frontier logo]()
$131
Find flight deals from Cleveland to Caribbean
Keep the following information in mind while searching for Cleveland to Caribbean flight deals. Data was last updated April 28, 2026.
Round-trip from | $198 (Kiwi.com) |
|---|---|
One-way from | $94 (eDestinos) |
Popular in | December |
Cheapest in | May |
Average price | $303 |
Good round-trip deal | $559 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Cleveland to Caribbean 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 28, 2026.
Use the filters below to find and compare flights from Cleveland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 5/27
7:45 am-3:55 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Sun 5/31
6:41 pm-6:27 pm
2 stops23h 46m
$263
ClevelandSaint Thomas Island
CLE - STT
CLESTT
Cleveland Hopkins Intl
Sat 5/9
7:00 am-5:00 pm
1 stop10h 00m
Saint Thomas Island Cyril E King
Wed 5/13
2:10 pm-10:44 pm
1 stop8h 34m
$290
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 5/2
7:05 am-4:23 pm
1 stop9h 18m
San Juan Luis Munoz Marin Intl
Wed 5/6
5:34 pm-12:34 am
1 stop7h 00m
$316
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Tue 6/30
5:44 am-2:00 pm
2 stops9h 16m
Montego Bay Sangster Intl
Tue 7/7
2:23 pm-9:12 am
1 stop17h 49m
$357
ClevelandOranjestad
CLE - AUA
CLEAUA
Cleveland Hopkins Intl
Sun 5/10
3:42 pm-2:36 pm
1 stop22h 54m
Oranjestad Reina Beatrix
Mon 6/1
3:41 pm-2:42 pm
1 stop23h 01m
$361
ClevelandSanto Domingo
CLE - SDQ
CLESDQ
Cleveland Hopkins Intl
Sat 5/23
7:24 pm-1:39 pm
2 stops18h 15m
Santo Domingo Las Americas
Sat 5/30
2:44 pm-7:48 am
2 stops17h 04m
$371
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Fri 7/31
6:26 am-1:30 pm
1 stop8h 04m
Montego Bay Sangster Intl
Sat 8/8
4:33 pm-11:14 am
1 stop17h 41m
$373
ClevelandOranjestad
CLE - AUA
CLEAUA
Cleveland Hopkins Intl
Sun 5/31
6:00 am-3:30 pm
1 stop9h 30m
Oranjestad Reina Beatrix
Fri 6/5
4:30 pm-11:44 pm
1 stop7h 14m
$375
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Tue 6/16
5:35 am-1:53 pm
1 stop8h 18m
Simpson Bay Princess Juliana
Wed 6/24
3:18 pm-12:47 am
1 stop9h 29m
$385
Quickest round-trip
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Wed 6/10
6:00 am-12:33 pm
1 stop6h 33m
Simpson Bay Princess Juliana
Wed 6/17
3:50 pm-11:44 pm
1 stop7h 54m
$385
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Cleveland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Cleveland with our price prediction graph.
CLE-SJU
CLE-PUJ
CLE-SXM
CLE-MBJ
CLE-NAS
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
CLE-0CB
CLE-SJU
CLE-PUJ
CLE-SXM
CLE-MBJ
How far ahead should I book a flight from Cleveland to Caribbean?
Booking 39 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Cleveland to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $113). Flying from Cleveland to Caribbean in October is currently the most expensive (average of $764). 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 CB?
Find hourly flight availability from Cleveland to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 28, 2026.
It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 69% on the flight price compared to flying at noon, which is usually more expensive.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated April 28, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Cleveland to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Food
7.0
Entertainment
7.5
Boarding
8.1
Overall
8.0
Comfort
8.0
Crew
8.6
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. 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Cleveland to Caribbean by cabin class
Find flights from Cleveland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Cleveland and Caribbean flights
Browse other Cleveland and Caribbean flight options. Last updated on April 28, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Cleveland to Caribbean flights
Consider these flights traveling from Cleveland to Caribbean.
Top 6 airlines flying from Cleveland to Caribbean
Discover the top 6 airlines that operate flights from Cleveland to Caribbean. 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 28, 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$171 | Average$439 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$586 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$544 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$571 | FlexibilityNo cancel fee | On-time63% |