$119+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jul 10 — Jul 171
Round-trip
1 adult, Economy
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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 June 10, 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 June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/139:23 am
CLE
- SJU
1 stop14h 36m
American Airlines
Fri 8/216:00 am
SJU
- CLE
1 stop17h 50m
American Airlines
Deal found 6/10![American Airlines logo]()
$238
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/269:43 am
CLE
- SJU
1 stop13h 32m
American Airlines
Tue 9/13:28 pm
SJU
- CLE
1 stop8h 16m
American Airlines
Deal found 6/10![American Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:59 pm
CLE
- SJU
1 stop24h 59m
Frontier
Tue 9/16:41 pm
SJU
- CLE
1 stop28h 31m
Frontier
Deal found 6/5![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/111:54 pm
CLE
- SJU
1 stop10h 47m
Frontier
Wed 8/266:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/5![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/234:34 pm
CLE
- SJU
1 stop7h 49m
Frontier
Wed 8/266:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/5![Frontier logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/194:34 pm
CLE
- SJU
1 stop7h 49m
Frontier
Wed 8/266:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/7![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Sun 8/306:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/5![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/12:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Thu 8/66:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/7![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:59 pm
CLE
- SJU
1 stop24h 59m
Frontier
Sun 8/306:00 am
SJU
- CLE
1 stop8h 38m
Frontier
Deal found 6/10![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:33 pm
CLE
- SJU
1 stop30h 08m
Frontier
Tue 8/116:00 am
SJU
- CLE
1 stop16h 57m
Frontier
Deal found 6/5![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Fri 8/285:01 pm
SJU
- CLE
1 stop7h 43m
Frontier
Deal found 6/5![Frontier logo]()
$285
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 10/65:00 am
CLE
- MBJ
1 stop9h 05m
American Airlines
Fri 10/1610:50 am
MBJ
- CLE
1 stop12h 15m
American Airlines
Deal found 6/8![American Airlines logo]()
$352
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 June 10, 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 June 10, 2026.
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:00 am
CLE
- SJU
1 stop6h 40m
United Airlines
Thu 11/122:05 am
SJU
- CLE
1 stop9h 53m
United Airlines
Deal found 6/7![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/412:35 pm
CLE
- SJU
1 stop9h 54m
Delta
Mon 9/77:30 am
SJU
- CLE
1 stop9h 03m
Delta
Deal found 6/10![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/411:00 am
CLE
- SJU
1 stop11h 50m
Southwest
Mon 9/75:30 am
SJU
- CLE
1 stop6h 45m
Southwest
Deal found 6/9![Southwest logo]()
$346
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/107:38 pm
CLE
- MBJ
2 stops18h 15m
American Airlines
Sun 9/135:16 pm
MBJ
- CLE
2 stops18h 13m
American Airlines
Deal found 6/5![American Airlines logo]()
$392
This Air Canada deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 stops26h 03m
Air Canada
Deal found 6/5![Air Canada logo]()
$455
This JetBlue deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:25 am
CLE
- NAS
1 stop9h 39m
JetBlue
Wed 8/125:24 pm
NAS
- CLE
1 stop6h 35m
JetBlue
Deal found 6/5![JetBlue logo]()
$471
This Orbitz deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/26:40 am
CLE
- PUJ
1 stop7h 41m
Frontier
Thu 8/611:50 am
PUJ
- CLE
Nonstop4h 30m
Frontier
Deal found 6/5![Frontier logo]()
$538
This FlightHub deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/157:00 pm
CLE
- UVF
1 stop19h 10m
Multiple Airlines
Mon 6/221:50 pm
UVF
- CLE
1 stop10h 09m
Multiple Airlines
Deal found 6/6![Multiple Airlines logo]()
$620
This Copa Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/275:20 am
CLE
- CUR
2 stops30h 58m
Copa Airlines
Sat 10/33:38 pm
CUR
- CLE
2 stops17h 57m
Copa Airlines
Deal found 6/5![Copa Airlines logo]()
$675
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:00 am
CLE
- SJU
2 stops11h 38m
United Airlines
Mon 10/53:56 pm
SJU
- CLE
1 stop8h 03m
United Airlines
Deal found 6/6![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 9/411:00 am
CLE
- SJU
1 stop11h 29m
Delta
Tue 9/85:45 pm
SJU
- CLE
1 stop6h 51m
Delta
Deal found 6/8![Delta logo]()
$346
This Southwest deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:15 am
CLE
- SJU
2 stops10h 15m
Southwest
Fri 11/1311:20 am
SJU
- CLE
2 stops9h 55m
Southwest
Deal found 6/8![Southwest logo]()
$355
This Southwest deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/1511:30 am
CLE
- SJU
1 stop13h 05m
Southwest
Thu 10/225:20 pm
SJU
- CLE
1 stop6h 50m
Southwest
Deal found 6/5![Southwest logo]()
$365
This United Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:00 am
CLE
- SJU
1 stop6h 40m
United Airlines
Wed 12/92:05 am
SJU
- CLE
2 stops10h 36m
United Airlines
Deal found 6/5![United Airlines logo]()
$367
This Delta deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:26 am
CLE
- MBJ
1 stop7h 18m
Delta
Wed 9/301:25 pm
MBJ
- CLE
1 stop10h 18m
Delta
Deal found 6/10![Delta logo]()
$372
This American Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/264:32 pm
CLE
- STT
2 stops20h 19m
American Airlines
Fri 10/21:41 pm
STT
- CLE
2 stops21h 33m
American Airlines
Deal found 6/5![American Airlines logo]()
$412
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/317:00 am
CLE
- SJU
1 stop6h 40m
United Airlines
Sat 11/78:30 am
SJU
- CLE
2 stops10h 50m
United Airlines
Deal found 6/9![United Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/138:13 pm
CLE
- STT
2 stops16h 27m
American Airlines
Tue 10/205:40 pm
STT
- CLE
2 stops17h 38m
American Airlines
Deal found 6/6![American Airlines logo]()
$412
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:40 pm
CLE
- MBJ
1 stop16h 45m
Delta
Sat 11/75:59 pm
MBJ
- CLE
1 stop15h 14m
Delta
Deal found 6/7![Delta logo]()
$382
This JetBlue deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:25 am
CLE
- NAS
1 stop9h 38m
JetBlue
Tue 9/15:24 pm
NAS
- CLE
1 stop6h 35m
JetBlue
Deal found 6/6![JetBlue logo]()
$471
This Air Canada deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 10/32:45 pm
CLE
- BGI
2 stops24h 40m
Air Canada
Wed 10/74:20 pm
BGI
- CLE
2 stops26h 03m
Air Canada
Deal found 6/9![Air Canada logo]()
$485
This Delta deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:25 am
CLE
- MBJ
1 stop6h 09m
Delta
Sat 11/75:59 pm
MBJ
- CLE
1 stop15h 14m
Delta
Deal found 6/7![Delta logo]()
$382
This American Airlines deal was found by Cheapflights users on 6/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/59:14 pm
CLE
- STT
2 stops17h 48m
American Airlines
Mon 9/74:42 pm
STT
- CLE
2 stops19h 15m
American Airlines
Deal found 6/10![American Airlines logo]()
$429
This JetBlue deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/146:25 am
CLE
- NAS
1 stop9h 39m
JetBlue
Wed 7/151:30 pm
NAS
- CLE
1 stop11h 29m
JetBlue
Deal found 6/9![JetBlue logo]()
$491
This Frontier deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/86:40 am
CLE
- PUJ
1 stop7h 41m
Frontier
Mon 7/1311:46 am
PUJ
- CLE
1 stop11h 52m
Frontier
Deal found 6/5![Frontier logo]()
$550
This Air Canada deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 6/137:00 pm
CLE
- PUJ
2 stops21h 30m
Air Canada
Mon 6/155:25 pm
PUJ
- CLE
1 stop24h 58m
Air Canada
Deal found 6/9![Air Canada logo]()
$528
This Delta deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/285:26 am
CLE
- STT
1 stop8h 08m
Delta
Mon 8/312:49 pm
STT
- CLE
1 stop9h 40m
Delta
Deal found 6/9![Delta logo]()
$408
This CheapOair deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/126:40 am
CLE
- MBJ
1 stop6h 44m
Frontier
Sun 7/261:39 pm
MBJ
- CLE
1 stop21h 10m
Frontier
Deal found 6/9![Frontier logo]()
$562
This United Airlines deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am
CLE
- STT
1 stop6h 58m
United Airlines
Sat 10/34:45 pm
STT
- CLE
1 stop7h 14m
United Airlines
Deal found 6/7![United Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:31 pm
CLE
- STT
2 stops20h 20m
American Airlines
Wed 10/71:50 pm
STT
- CLE
2 stops9h 51m
American Airlines
Deal found 6/6![American Airlines logo]()
$482
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated June 10, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated June 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/204:36 pm
CLE
- SJU
1 stop7h 39m
Frontier
Thu 6/256:00 am
SJU
- CLE
1 stop16h 54m
Frontier
Deal found 6/5![Frontier logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/297:45 am
CLE
- SJU
1 stop8h 13m
Frontier
Thu 7/97:30 am
SJU
- CLE
1 stop16h 08m
Frontier
Deal found 6/7![Frontier logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/302:05 pm
CLE
- SJU
1 stop10h 32m
Frontier
Thu 7/96:00 am
SJU
- CLE
1 stop16h 57m
Frontier
Deal found 6/7![Frontier logo]()
$316
This United Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/36:26 am
CLE
- MBJ
1 stop8h 04m
United Airlines
Thu 7/94:12 pm
MBJ
- CLE
1 stop6h 32m
United Airlines
Deal found 6/9![United Airlines logo]()
$382
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:20 pm
CLE
- SJU
1 stop30h 21m
Frontier
Thu 7/237:30 am
SJU
- CLE
1 stop16h 08m
Frontier
Deal found 6/6![Frontier logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com 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
Thu 7/306:00 am
SJU
- CLE
1 stop8h 36m
Frontier
Deal found 6/5![Frontier logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Fri 8/215:01 pm
SJU
- CLE
1 stop7h 43m
Frontier
Deal found 6/7![Frontier logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/212:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Sat 8/225:01 pm
SJU
- CLE
1 stop7h 43m
Frontier
Deal found 6/7![Frontier logo]()
$304
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 7/226:01 am
CLE
- SJU
1 stop15h 58m
American Airlines
Wed 8/127:00 am
SJU
- CLE
1 stop16h 30m
American Airlines
Deal found 6/9![American Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:20 pm
CLE
- SJU
1 stop30h 21m
Frontier
Thu 8/67:10 am
SJU
- CLE
1 stop16h 28m
Frontier
Deal found 6/6![Frontier logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:30 am
CLE
- SJU
1 stop18h 11m
Frontier
Sat 8/86:00 am
SJU
- CLE
1 stop16h 57m
Frontier
Deal found 6/5![Frontier logo]()
$292
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:30 am
CLE
- SJU
1 stop18h 11m
Frontier
Sun 8/97:10 am
SJU
- CLE
1 stop16h 28m
Frontier
Deal found 6/5![Frontier logo]()
$313
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 June 10, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 10, 2026.
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 8/46:29 am
CLE
- SJU
1 stop16h 28m
American Airlines
Deal found 6/9![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 10/2012:19 pm
CLE
- SJU
1 stop11h 31m
American Airlines
Deal found 6/8![American Airlines logo]()
$121
This American Airlines deal was found by Cheapflights users on 6/9. Clicking the “Pick Dates” 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 9/212:16 pm
CLE
- SJU
1 stop10h 08m
American Airlines
Deal found 6/9![American Airlines logo]()
$124
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/282:04 pm
CLE
- SJU
1 stop10h 37m
Frontier
Deal found 6/7![Frontier logo]()
$143
This United Airlines deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/76:00 am
CLE
- STT
1 stop6h 20m
United Airlines
Deal found 6/8![United Airlines logo]()
$143
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/294:34 pm
CLE
- SJU
1 stop7h 49m
Frontier
Deal found 6/7![Frontier logo]()
$144
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:30 am
CLE
- SJU
1 stop17h 53m
Frontier
Deal found 6/7![Frontier logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 6/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:20 pm
CLE
- SJU
1 stop30h 21m
Frontier
Deal found 6/7![Frontier logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/284:05 pm
CLE
- SJU
1 stop23h 53m
Frontier
Deal found 6/5![Frontier logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:20 pm
CLE
- SJU
1 stop30h 21m
Frontier
Deal found 6/5![Frontier logo]()
$157
This Kiwi.com deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:30 am
CLE
- SJU
1 stop18h 07m
Frontier
Deal found 6/6![Frontier logo]()
$158
This Expedia deal was found by Cheapflights users on 6/8. Clicking the “Pick Dates” 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 11/206:10 pm
CLE
- BGI
1 stop19h 25m
Air Canada
Deal found 6/8![Air Canada logo]()
$160
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 June 10, 2026.
Round-trip from | $238 (American Airlines) |
|---|---|
One-way from | $119 (American Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $394 |
Good round-trip deal | $585 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 June 10, 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
Thu 10/29
7:00 am-1:40 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Thu 11/12
2:05 am-10:58 am
1 stop9h 53m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 9/4
12:35 pm-10:29 pm
1 stop9h 54m
San Juan Luis Munoz Marin Intl
Mon 9/7
7:30 am-4:33 pm
1 stop9h 03m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 9/4
11:00 am-10:50 pm
1 stop11h 50m
San Juan Luis Munoz Marin Intl
Mon 9/7
5:30 am-12:15 pm
1 stop6h 45m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 9/30
9:00 am-8:38 pm
2 stops11h 38m
San Juan Luis Munoz Marin Intl
Mon 10/5
3:56 pm-11:59 pm
1 stop8h 03m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 9/4
11:00 am-10:29 pm
1 stop11h 29m
San Juan Luis Munoz Marin Intl
Tue 9/8
5:45 pm-12:36 am
1 stop6h 51m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Thu 10/29
6:15 am-4:30 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Fri 11/13
11:20 am-8:15 pm
2 stops9h 55m
$355
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Thu 10/15
11:30 am-12:35 am
1 stop13h 05m
San Juan Luis Munoz Marin Intl
Thu 10/22
5:20 pm-12:10 am
1 stop6h 50m
$365
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 12/5
7:00 am-2:40 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Wed 12/9
2:05 am-11:41 am
2 stops10h 36m
$367
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 10/31
7:00 am-1:40 pm
1 stop6h 40m
San Juan Luis Munoz Marin Intl
Sat 11/7
8:30 am-6:20 pm
2 stops10h 50m
$368
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Tue 9/1
5:26 am-11:44 am
1 stop7h 18m
Montego Bay Sangster Intl
Wed 9/30
1:25 pm-12:43 am
1 stop10h 18m
$372
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-MBJ
CLE-BGI
CLE-NAS
CLE-PUJ
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-MBJ
CLE-BGI
CLE-NAS
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 $138). Flying from Cleveland to Caribbean in October is currently the most expensive (average of $1,030). 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 June 10, 2026.
It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 67% on the flight price compared to flying at noon, which is usually more expensive.
How far ahead should I book a flight from Cleveland to Caribbean?
Booking 16 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.
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 June 10, 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.
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Boarding
8.1
Entertainment
7.5
Comfort
8.0
Food
7.0
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 10, 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 7 airlines flying from Cleveland to Caribbean
Discover the top 7 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 June 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$114 | Average$523 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$388 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$160 | Average$534 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$181 | Average$452 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$547 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$225 | Average$605 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$609 | FlexibilityNo cancel fee | On-time63% |