$129+ 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 9/14. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Sep 17 — Sep 241
Round-trip
1 adult, Economy
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Find cheap flights from Cleveland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 August 18, 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 August 18, 2026.
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop7h 32m
Tue 10/202:18 pm -
2 stops9h 21m
Deal found 8/13![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
2 stops25h 05m
Tue 9/158:45 am -
1 stop11h 17m
Deal found 8/13![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1010:07 am -
1 stop6h 59m
Sun 10/184:34 pm -
2 stops52h 18m
Deal found 8/14![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:05 pm -
1 stop24h 06m
Sat 8/227:30 am -
1 stop16h 56m
Deal found 8/14![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:38 pm -
1 stop23h 33m
Tue 9/16:35 am -
1 stop16h 54m
Deal found 8/14![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:07 pm -
1 stop7h 36m
Mon 8/246:35 am -
1 stop8h 25m
Deal found 8/17![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:38 pm -
1 stop23h 33m
Fri 8/286:35 am -
1 stop8h 25m
Deal found 8/13![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:10 pm -
1 stop18h 07m
Mon 9/283:08 am -
2 stops41h 44m
Deal found 8/17![Frontier logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:07 pm -
1 stop7h 36m
Sat 8/226:35 am -
1 stop8h 25m
Deal found 8/16![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:05 pm -
1 stop24h 06m
Fri 8/216:35 am -
1 stop16h 54m
Deal found 8/14![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:08 pm -
1 stop18h 19m
Tue 10/66:05 pm -
2 stops42h 04m
Deal found 8/14![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 8/164:05 pm -
1 stop24h 06m
Sat 8/226:35 am -
1 stop8h 25m
Deal found 8/16![Frontier logo]()
$272
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 August 18, 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 August 18, 2026.
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 11/912:35 pm -
2 stops9h 20m
Thu 11/124:00 pm -
2 stops8h 45m
Deal found 8/16![Southwest logo]()
$374
This Orbitz deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/36:55 pm -
1 stop19h 50m
Sat 12/123:45 pm -
2 stops27h 34m
Deal found 8/14![Air Canada logo]()
$391
This Delta deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/47:15 am -
1 stop10h 51m
Tue 11/103:55 pm -
1 stop10h 03m
Deal found 8/17![Delta logo]()
$406
This United Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:10 am -
1 stop7h 37m
Fri 10/232:35 pm -
1 stop7h 24m
Deal found 8/15![United Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/46:00 am -
2 stops12h 53m
Tue 11/107:00 am -
2 stops12h 07m
Deal found 8/17![American Airlines logo]()
$416
This Travelocity deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/66:55 pm -
2 stops18h 50m
Wed 11/112:09 pm -
1 stop10h 50m
Deal found 8/15![Multiple Airlines logo]()
$454
This Copa Airlines deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/68:30 am -
2 stops29h 07m
Sun 12/137:22 pm -
2 stops26h 21m
Deal found 8/14![Copa Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/211:50 pm -
2 stops9h 20m
Mon 9/286:30 am -
2 stops10h 15m
Deal found 8/16![Southwest logo]()
$387
This Air Canada deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:55 pm -
1 stop19h 50m
Wed 11/114:45 pm -
1 stop26h 32m
Deal found 8/13![Air Canada logo]()
$395
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 am -
1 stop7h 32m
Sat 11/146:45 am -
2 stops15h 18m
Deal found 8/13![Delta logo]()
$418
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/206:24 am -
1 stop7h 24m
Wed 11/2512:55 pm -
1 stop8h 49m
Deal found 8/17![United Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/161:15 pm -
2 stops8h 50m
Tue 9/228:20 am -
2 stops10h 10m
Deal found 8/14![Southwest logo]()
$394
This FlightHub deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/286:55 pm -
1 stop19h 50m
Sat 12/123:45 pm -
2 stops27h 34m
Deal found 8/15![Air Canada logo]()
$399
This FlightHub deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/76:55 pm -
1 stop19h 50m
Wed 11/112:09 pm -
1 stop10h 50m
Deal found 8/15![Multiple Airlines logo]()
$456
This Delta deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/296:00 am -
1 stop7h 53m
Tue 10/61:10 pm -
1 stop9h 52m
Deal found 8/14![Delta logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/164:07 pm -
1 stop6h 39m
Thu 10/156:00 am -
1 stop14h 06m
Deal found 8/17![United Airlines logo]()
$430
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/2211:40 am -
2 stops9h 30m
Sat 9/266:25 am -
2 stops10h 20m
Deal found 8/14![Southwest logo]()
$397
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/76:00 am -
1 stop9h 50m
Tue 1/125:59 pm -
1 stop17h 18m
Deal found 8/17![American Airlines logo]()
$481
This Orbitz deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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.
Fri 12/46:55 pm -
2 stops41h 55m
Tue 12/82:25 pm -
2 stops27h 54m
Deal found 8/16![Air Canada logo]()
$400
This Delta deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/206:15 am -
1 stop7h 15m
Wed 1/271:20 pm -
2 stops10h 26m
Deal found 8/13![Delta logo]()
$426
This Travelocity deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:55 pm -
1 stop17h 30m
Mon 11/232:15 pm -
1 stop8h 33m
Deal found 8/17![Multiple Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:10 am -
2 stops10h 30m
Sat 9/1910:25 am -
2 stops10h 00m
Deal found 8/17![Southwest logo]()
$400
This American Airlines deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/305:12 am -
2 stops9h 58m
Fri 11/64:10 pm -
2 stops18h 22m
Deal found 8/17![American Airlines logo]()
$486
This Justfly.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:55 pm -
1 stop17h 30m
Mon 11/91:20 pm -
1 stop28h 57m
Deal found 8/14![Air Canada logo]()
$403
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 am -
1 stop7h 10m
Fri 10/96:00 am -
1 stop15h 59m
Deal found 8/13![United Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/302:35 pm -
1 stop7h 09m
Wed 1/62:40 pm -
2 stops9h 06m
Deal found 8/12![Delta logo]()
$426
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/106:19 am -
1 stop12h 15m
Mon 9/1410:21 am -
2 stops13h 21m
Deal found 8/13![American Airlines logo]()
$497
This Expedia deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:55 pm -
1 stop17h 30m
Tue 12/11:20 pm -
1 stop28h 59m
Deal found 8/13![Air Canada logo]()
$413
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/1310:55 am -
2 stops9h 35m
Mon 10/196:30 am -
2 stops10h 40m
Deal found 8/13![Southwest logo]()
$420
This Delta deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/57:16 am -
1 stop10h 13m
Mon 10/122:57 pm -
1 stop10h 00m
Deal found 8/16![Delta logo]()
$436
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated August 18, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated August 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/174:05 pm -
1 stop24h 06m
Mon 8/318:57 pm -
1 stop10h 59m
Deal found 8/14![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:38 pm -
1 stop23h 33m
Tue 9/16:35 am -
1 stop16h 54m
Deal found 8/14![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/184:38 pm -
1 stop23h 33m
Sun 8/237:30 am -
1 stop16h 56m
Deal found 8/14![Frontier logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/205:07 pm -
1 stop7h 36m
Sat 8/226:35 am -
1 stop8h 25m
Deal found 8/16![Frontier logo]()
$267
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:07 pm -
1 stop7h 36m
Mon 8/246:35 am -
1 stop8h 25m
Deal found 8/17![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/244:38 pm -
1 stop23h 33m
Fri 8/286:35 am -
1 stop8h 25m
Deal found 8/13![Frontier logo]()
$265
This Kiwi.com deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
2 stops25h 05m
Tue 9/158:45 am -
1 stop11h 17m
Deal found 8/13![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am -
2 stops19h 13m
Sat 9/1910:30 am -
1 stop28h 00m
Deal found 8/17![Frontier logo]()
$272
This United Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:00 am -
1 stop6h 33m
Thu 9/172:35 pm -
1 stop7h 16m
Deal found 8/13![United Airlines logo]()
$412
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 9/146:57 pm -
1 stop7h 16m
Wed 9/164:39 pm -
2 stops19h 25m
Deal found 8/16![Frontier logo]()
$273
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/229:10 pm -
1 stop18h 07m
Mon 9/283:08 am -
2 stops41h 44m
Deal found 8/17![Frontier logo]()
$266
This American Airlines deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop7h 32m
Tue 10/202:18 pm -
2 stops9h 21m
Deal found 8/13![American Airlines logo]()
$259
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 August 18, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:45 pm -
2 stops25h 00m
Deal found 8/17![Frontier logo]()
$129
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/153:45 pm -
2 stops23h 32m
Deal found 8/17![Frontier logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:45 pm -
2 stops25h 18m
Deal found 8/17![Frontier logo]()
$134
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:51 am -
1 stop29h 40m
Deal found 8/17![Frontier logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 8/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/197:45 am -
1 stop9h 18m
Deal found 8/17![Frontier logo]()
$138
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/163:45 pm -
2 stops32h 13m
Deal found 8/14![Frontier logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/103:45 pm -
2 stops32h 13m
Deal found 8/14![Frontier logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 -
2 stops16h 58m
Deal found 8/16![Frontier logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” 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 10/133:46 pm -
1 stop24h 20m
Deal found 8/16![Frontier logo]()
$144
This Orbitz deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/182:45 pm -
2 stops26h 45m
Deal found 8/15![Air Canada logo]()
$146
This United Airlines deal was found by Cheapflights users on 8/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/186:10 am -
1 stop7h 37m
Deal found 8/15![United Airlines logo]()
$152
This Travelocity deal was found by Cheapflights users on 8/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/26:55 pm -
1 stop17h 30m
Deal found 8/16![Air Canada logo]()
$165
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 August 18, 2026.
Round-trip from | $259 (American Airlines) |
|---|---|
One-way from | $129 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $361 |
Good round-trip deal | $599 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 August 18, 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 Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Mon 11/9
12:35 pm-10:55 pm
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Thu 11/12
4:00 pm-11:45 pm
2 stops8h 45m
$374
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Mon 9/21
1:50 pm-11:10 pm
2 stops9h 20m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:30 am-4:45 pm
2 stops10h 15m
$387
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Thu 12/3
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Sat 12/12
3:45 pm-6:19 pm
2 stops27h 34m
$391
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Wed 9/16
1:15 pm-10:05 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Tue 9/22
8:20 am-6:30 pm
2 stops10h 10m
$394
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/7
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Wed 11/11
4:45 pm-6:17 pm
1 stop26h 32m
$395
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Tue 9/22
11:40 am-9:10 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Sat 9/26
6:25 am-4:45 pm
2 stops10h 20m
$397
ClevelandSimpson Bay
CLE Cleveland Hopkins Intl - SXM Simpson Bay Princess Juliana
CLESXM
Cleveland Hopkins Intl
Sat 11/28
6:55 pm-3:45 pm
1 stop19h 50m
Simpson Bay Princess Juliana
Sat 12/12
3:45 pm-6:19 pm
2 stops27h 34m
$399
ClevelandProvidenciales
CLE Cleveland Hopkins Intl - PLS Providenciales
CLEPLS
Cleveland Hopkins Intl
Fri 12/4
6:55 pm-12:50 pm
2 stops41h 55m
Providenciales
Tue 12/8
2:25 pm-6:19 pm
2 stops27h 54m
$400
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sat 9/12
6:10 am-4:40 pm
2 stops10h 30m
San Juan Luis Munoz Marin Intl
Sat 9/19
10:25 am-8:25 pm
2 stops10h 00m
$400
ClevelandProvidenciales
CLE Cleveland Hopkins Intl - PLS Providenciales
CLEPLS
Cleveland Hopkins Intl
Mon 11/2
6:55 pm-12:25 pm
1 stop17h 30m
Providenciales
Mon 11/9
1:20 pm-6:17 pm
1 stop28h 57m
$403
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-NAS
CLE-PLS
CLE-SXM
CLE-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Cleveland to Caribbean
CLE-0CB
CLE-SJU
CLE-NAS
CLE-PLS
CLE-SXM
What is the cheapest month to book a flight from Cleveland to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $459). Flying from Cleveland to Caribbean in June is currently the most expensive (average of $579). 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 August 18, 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 40 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 August 18, 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
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Boarding
8.1
Comfort
8.0
Entertainment
7.5
Crew
8.6
Food
7.0
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
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 August 18, 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 August 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$151 | Average$389 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$168 | Average$536 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$184 | Average$568 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$187 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$596 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$229 | Average$545 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$623 | FlexibilityNo cancel fee | On-time63% |