$122+ Cheap flights from Cleveland (CLE) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Oct 8 — Oct 151
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Cleveland to Caribbean
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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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sun 10/47:38 pm -
1 stop15h 42m
Sat 10/106:00 am -
1 stop12h 51m
Deal found 9/5![American Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/31:35 pm -
1 stop7h 13m
Thu 10/85:11 pm -
1 stop18h 58m
Deal found 9/4![Frontier logo]()
$255
This Priceline deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:10 pm -
1 stop16h 24m
Tue 10/61:47 pm -
1 stop7h 05m
Deal found 9/4![Frontier logo]()
$256
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:59 pm -
1 stop19h 44m
Sat 9/266:42 pm -
1 stop14h 25m
Deal found 9/3![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/63:45 pm -
2 stops24h 37m
Mon 10/123:55 pm -
1 stop8h 24m
Deal found 9/7![Frontier logo]()
$258
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 11/116:05 pm -
1 stop17h 29m
Tue 11/179:45 am -
1 stop8h 40m
Deal found 9/5![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/259:59 pm -
1 stop11h 36m
Tue 9/298:45 am -
1 stop11h 17m
Deal found 9/4![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/267:00 am -
1 stop9h 06m
Sun 9/277:00 am -
1 stop7h 30m
Deal found 9/4![Frontier logo]()
$261
This Priceline deal was found by Cheapflights users on 9/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:20 am -
1 stop19h 32m
Wed 9/3010:42 am -
1 stop22h 25m
Deal found 9/7![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/267:00 am -
1 stop9h 06m
Wed 9/302:57 am -
2 stops9h 07m
Deal found 9/4![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/31:35 pm -
1 stop7h 13m
Wed 10/76:30 am -
1 stop14h 22m
Deal found 9/4![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/223:45 pm -
1 stop23h 37m
Tue 10/61:47 pm -
1 stop7h 05m
Deal found 9/4![Frontier logo]()
$265
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 September 8, 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 September 8, 2026.
This Priceline deal was found by Cheapflights users on 9/8. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/259:59 pm -
1 stop22h 49m
Sun 10/42:57 am -
1 stop21h 33m
Deal found 9/8![Frontier logo]()
$262
This Air Canada deal was found by Cheapflights users on 9/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/237:00 pm -
1 stop22h 00m
Fri 10/303:45 pm -
1 stop26h 32m
Deal found 9/8![Air Canada logo]()
$349
This Southwest deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/101:55 pm -
2 stops9h 50m
Fri 11/134:00 pm -
2 stops8h 45m
Deal found 9/4![Southwest logo]()
$374
This Delta deal was found by Cheapflights users on 9/7. 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 11/77:15 am -
1 stop10h 51m
Thu 11/127:02 am -
1 stop10h 27m
Deal found 9/7![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 10/196:00 am -
1 stop6h 40m
Fri 10/233:35 pm -
1 stop8h 24m
Deal found 9/6![United Airlines logo]()
$408
This JetBlue deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:00 am -
1 stop6h 25m
Thu 10/292:54 pm -
1 stop8h 01m
Deal found 9/3![JetBlue logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:38 pm -
1 stop15h 01m
Thu 10/291:39 pm -
2 stops10h 20m
Deal found 9/3![American Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 11/113:46 pm -
2 stops20h 25m
Tue 11/179:25 am -
1 stop24h 41m
Deal found 9/7![Multiple Airlines logo]()
$458
This Copa Airlines deal was found by Cheapflights users on 9/5. 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 10/115:20 am -
2 stops30h 58m
Sun 10/183:38 pm -
2 stops17h 57m
Deal found 9/5![Copa Airlines logo]()
$701
This Delta deal was found by Cheapflights users on 9/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/281:00 pm -
2 stops23h 55m
Thu 11/53:10 pm -
1 stop8h 52m
Deal found 9/5![Delta logo]()
$410
This Expedia deal was found by Cheapflights users on 9/6. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/186:55 pm -
2 stops42h 20m
Sun 11/222:05 pm -
2 stops28h 12m
Deal found 9/6![Air Canada logo]()
$410
This FlightHub deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Sun 10/47:00 am -
1 stop8h 27m
Thu 10/83:48 pm -
1 stop19h 21m
Deal found 9/3![Frontier logo]()
$412
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am -
1 stop7h 10m
Sat 10/315:00 am -
1 stop15h 47m
Deal found 9/3![United Airlines logo]()
$422
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/206:00 am -
1 stop5h 05m
Tue 10/2712:05 pm -
1 stop11h 35m
Deal found 9/3![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:10 am -
2 stops17h 04m
Thu 11/263:57 pm -
1 stop8h 58m
Deal found 9/6![Delta logo]()
$413
This Justfly.com deal was found by Cheapflights users on 9/8. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/266:55 pm -
1 stop19h 50m
Sat 12/53:45 pm -
2 stops27h 34m
Deal found 9/8![Air Canada logo]()
$415
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/187:00 am -
1 stop8h 33m
Sun 10/253:48 pm -
1 stop28h 04m
Deal found 9/3![Frontier logo]()
$420
This Southwest deal was found by Cheapflights users on 9/7. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/181:55 pm -
2 stops9h 50m
Mon 11/2312:40 pm -
2 stops9h 20m
Deal found 9/7![Southwest logo]()
$473
This United Airlines deal was found by Cheapflights users on 9/5. 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.
Tue 9/297:00 am -
1 stop7h 10m
Tue 10/61:10 pm -
1 stop8h 49m
Deal found 9/5![United Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:00 am -
1 stop7h 07m
Sat 10/2412:07 pm -
1 stop11h 52m
Deal found 9/7![American Airlines logo]()
$432
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/235:09 pm -
1 stop8h 05m
Tue 12/18:53 pm -
2 stops18h 14m
Deal found 9/6![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 stop6h 33m
Fri 10/92:35 pm -
1 stop7h 24m
Deal found 9/4![United Airlines logo]()
$432
This American Airlines deal was found by Cheapflights users on 9/8. 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.
Sat 11/79:19 pm -
2 stops18h 12m
Wed 11/112:26 pm -
1 stop10h 21m
Deal found 9/8![American Airlines logo]()
$432
This JetBlue deal was found by Cheapflights users on 9/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:00 am -
1 stop6h 48m
Fri 10/3011:45 am -
1 stop10h 10m
Deal found 9/7![JetBlue logo]()
$534
This Southwest deal was found by Cheapflights users on 9/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:45 am -
2 stops11h 10m
Mon 11/1610:45 am -
2 stops8h 40m
Deal found 9/6![Southwest logo]()
$491
This Delta deal was found by Cheapflights users on 9/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:00 am -
1 stop7h 32m
Wed 10/282:57 pm -
1 stop10h 00m
Deal found 9/6![Delta logo]()
$414
This Travelocity deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Sun 11/226:55 pm -
1 stop25h 45m
Thu 11/2610:16 am -
Nonstop4h 48m
Deal found 9/3![Multiple Airlines logo]()
$562
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/197:00 am -
1 stop6h 33m
Mon 10/262:55 pm -
1 stop6h 49m
Deal found 9/3![United Airlines logo]()
$432
This Southwest deal was found by Cheapflights users on 9/5. 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.
Tue 12/11:55 pm -
2 stops9h 50m
Mon 12/710:45 am -
2 stops8h 40m
Deal found 9/5![Southwest logo]()
$500
This Delta deal was found by Cheapflights users on 9/7. 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.
Mon 10/197:15 am -
1 stop10h 51m
Tue 10/277:35 pm -
1 stop15h 16m
Deal found 9/7![Delta logo]()
$414
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated September 8, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/209:59 pm -
1 stop19h 44m
Sat 9/266:42 pm -
1 stop14h 25m
Deal found 9/3![Frontier logo]()
$257
This Priceline deal was found by Cheapflights users on 9/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/216:20 am -
1 stop19h 32m
Wed 9/3010:42 am -
1 stop22h 25m
Deal found 9/7![Frontier logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/223:45 pm -
1 stop23h 37m
Tue 10/61:47 pm -
1 stop7h 05m
Deal found 9/4![Frontier logo]()
$265
This Priceline deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/239:10 pm -
1 stop16h 24m
Tue 10/61:47 pm -
1 stop7h 05m
Deal found 9/4![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/259:59 pm -
1 stop11h 36m
Tue 9/298:45 am -
1 stop11h 17m
Deal found 9/4![Frontier logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/267:00 am -
1 stop9h 06m
Sun 9/277:00 am -
1 stop7h 30m
Deal found 9/4![Frontier logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/267:00 am -
1 stop9h 06m
Wed 9/302:57 am -
2 stops9h 07m
Deal found 9/4![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/31:35 pm -
1 stop7h 13m
Thu 10/85:11 pm -
1 stop18h 58m
Deal found 9/4![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/31:35 pm -
1 stop7h 13m
Wed 10/76:30 am -
1 stop14h 22m
Deal found 9/4![Frontier logo]()
$264
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Sun 10/47:38 pm -
1 stop15h 42m
Sat 10/106:00 am -
1 stop12h 51m
Deal found 9/5![American Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/63:45 pm -
2 stops24h 37m
Mon 10/123:55 pm -
1 stop8h 24m
Deal found 9/7![Frontier logo]()
$258
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 10/75:12 am -
1 stop8h 51m
Tue 10/136:30 am -
2 stops10h 15m
Deal found 9/5![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 September 8, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/306:00 am -
1 stop19h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$122
This Kiwi.com deal was found by Cheapflights users on 9/7. 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 10/63:45 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$123
This Kiwi.com deal was found by Cheapflights users on 9/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:46 pm -
1 stop23h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$123
This Mytrip deal was found by Cheapflights users on 9/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:00 am -
1 stop8h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Sun 9/277:00 am -
2 stops30h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$126
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/18:30 am -
1 stop14h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$127
This Kiwi.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/19:59 pm -
1 stop27h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$128
This eDestinos deal was found by Cheapflights users on 9/7. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/37:00 am -
1 stop9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![Frontier logo]()
$129
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Sat 10/36:42 pm -
2 stops14h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Wed 9/306:00 am -
1 stop7h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$132
This Booking.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:59 pm -
1 stop11h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$133
This American Airlines deal was found by Cheapflights users on 9/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/156:00 am -
1 stop5h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$162
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 September 8, 2026.
Round-trip from | $254 (American Airlines) |
|---|---|
One-way from | $122 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $381 |
Good round-trip deal | $775 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 7,457,451 searches. Data last updated September 8, 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
Tue 11/10
7:00 am-4:17 pm
2 stops32h 17m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$122
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sun 12/6
3:38 pm-11:52 pm
1 stop7h 14m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$123
ClevelandMontego Bay
CLE Cleveland Hopkins Intl - MBJ Montego Bay Sangster Intl
CLEMBJ
Cleveland Hopkins Intl
Sat 11/7
3:46 pm-3:29 pm
1 stop23h 43m
Montego Bay Sangster Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$123
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Tue 12/1
10:51 am-9:36 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$127
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sat 11/14
5:06 am-3:03 pm
2 stops8h 57m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$127
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sun 11/1
8:30 am-12:16 am
1 stop14h 46m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$127
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sat 10/3
7:00 am-4:06 pm
1 stop9h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Thu 10/22
7:00 am-10:19 am
2 stops27h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$130
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Mon 10/5
3:45 pm-1:52 am
2 stops10h 07m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$131
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Wed 9/30
3:45 pm-12:01 am
2 stops32h 16m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$136
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-PUJ
CLE-PLS
CLE-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Cleveland to Caribbean
CLE-0CB
CLE-SJU
CLE-NAS
CLE-PUJ
CLE-PLS
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 $451). 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 September 8, 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 September 8, 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
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
Boarding
8.1
Comfort
8.0
Overall
8.0
Food
7.0
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
4.0
OkaySteven,Sep 2026
OGG - HNL
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 September 8, 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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$571 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$187 | Average$502 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$627 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$237 | Average$544 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$275 | Average$624 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$325 | Average$600 | FlexibilityNo cancel fee | On-time62% |