$99+ 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 11/14. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Nov 22 — Nov 291
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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 October 23, 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 October 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/289:18 pm -
1 stop15h 28m
Wed 11/257:31 am -
1 stop17h 54m
Deal found 10/21![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:18 pm -
1 stop17h 01m
Fri 11/137:00 am -
1 stop13h 02m
Deal found 10/23![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:21 pm -
2 stops20h 15m
Sun 11/156:00 am -
1 stop30h 00m
Deal found 10/22![Frontier logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:18 pm -
1 stop15h 07m
Sat 11/74:52 pm -
1 stop19h 08m
Deal found 10/21![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:51 am -
1 stop14h 04m
Thu 10/296:00 am -
1 stop29h 00m
Deal found 10/21![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/116:35 am -
2 stops19h 11m
Fri 11/133:55 pm -
1 stop22h 39m
Deal found 10/21![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:21 pm -
2 stops20h 15m
Thu 11/193:42 am -
1 stop7h 14m
Deal found 10/22![Frontier logo]()
$235
This CheapOair deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 11/79:59 pm -
1 stop11h 16m
Thu 11/127:00 am -
1 stop8h 16m
Deal found 10/21![Frontier logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:18 pm -
1 stop17h 59m
Tue 11/38:45 am -
1 stop12h 18m
Deal found 10/20![Frontier logo]()
$238
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:28 am -
1 stop29h 18m
Tue 11/1011:20 am -
1 stop22h 46m
Deal found 10/23![Frontier logo]()
$239
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:18 pm -
1 stop25h 36m
Sat 11/217:31 am -
1 stop17h 54m
Deal found 10/22![Frontier logo]()
$241
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/147:00 am -
1 stop8h 40m
Thu 12/171:15 pm -
1 stop10h 24m
Deal found 10/20![JetBlue logo]()
$326
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 October 23, 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 October 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:18 pm -
1 stop24h 59m
Sun 11/17:00 am -
1 stop8h 16m
Deal found 10/22![Frontier logo]()
$272
This JetBlue deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/147:00 am -
1 stop8h 40m
Thu 12/171:15 pm -
1 stop10h 24m
Deal found 10/18![JetBlue logo]()
$326
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/912:40 pm -
2 stops9h 45m
Wed 12/166:40 am -
1 stop6h 20m
Deal found 10/20![Southwest logo]()
$384
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:05 am -
1 stop11h 25m
Tue 11/243:57 pm -
1 stop10h 00m
Deal found 10/18![Delta logo]()
$416
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/87:00 am -
1 stop8h 50m
Thu 1/143:00 pm -
1 stop8h 28m
Deal found 10/20![United Airlines logo]()
$422
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:18 am -
1 stop12h 07m
Fri 11/68:00 am -
1 stop11h 02m
Deal found 10/22![Multiple Airlines logo]()
$430
This Air Canada deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/297:00 pm -
1 stop19h 45m
Thu 12/33:30 pm -
2 stops27h 49m
Deal found 10/22![Air Canada logo]()
$474
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/175:15 am -
1 stop11h 31m
Wed 12/2311:17 am -
1 stop12h 42m
Deal found 10/18![American Airlines logo]()
$492
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:00 am -
1 stop9h 40m
Thu 12/31:05 pm -
1 stop10h 39m
Deal found 10/22![JetBlue logo]()
$345
This Copa Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:45 pm -
2 stops39h 33m
Sun 11/151:15 pm -
2 stops21h 23m
Deal found 10/21![Copa Airlines logo]()
$743
This JetBlue deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/26:00 am -
1 stop8h 25m
Tue 2/91:05 pm -
1 stop10h 54m
Deal found 10/21![JetBlue logo]()
$381
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 2/16:00 am -
1 stop9h 50m
Sun 2/75:50 pm -
1 stop7h 09m
Deal found 10/20![United Airlines logo]()
$422
This Southwest deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:55 pm -
2 stops9h 55m
Mon 12/712:30 pm -
2 stops9h 45m
Deal found 10/22![Southwest logo]()
$450
This Delta deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 2/26:05 am -
1 stop9h 40m
Tue 2/94:35 pm -
1 stop7h 41m
Deal found 10/18![Delta logo]()
$454
This United Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 12/126:00 am -
1 stop9h 50m
Wed 12/165:35 pm -
1 stop7h 24m
Deal found 10/18![United Airlines logo]()
$426
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/29:14 pm -
1 stop19h 19m
Sat 1/912:54 pm -
1 stop10h 04m
Deal found 10/22![Frontier logo]()
$469
This JetBlue deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/213:30 pm -
1 stop10h 27m
Thu 11/263:04 pm -
1 stop9h 45m
Deal found 10/18![JetBlue logo]()
$394
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/176:00 am -
1 stop5h 14m
Wed 11/2511:49 am -
1 stop11h 46m
Deal found 10/18![American Airlines logo]()
$492
This Southwest deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/115:35 am -
1 stop6h 45m
Fri 1/152:05 pm -
2 stops9h 35m
Deal found 10/20![Southwest logo]()
$460
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 3/87:15 am -
1 stop11h 45m
Tue 3/236:35 am -
2 stops16h 11m
Deal found 10/20![Delta logo]()
$467
This American Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/298:09 pm -
2 stops17h 16m
Sat 12/54:36 pm -
2 stops17h 59m
Deal found 10/22![American Airlines logo]()
$492
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/86:00 am -
1 stop8h 25m
Wed 1/132:10 pm -
1 stop9h 49m
Deal found 10/22![JetBlue logo]()
$424
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/1611:51 am -
1 stop10h 55m
Thu 11/196:00 am -
1 stop16h 44m
Deal found 10/21![United Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/1511:27 am -
2 stops25h 28m
Thu 12/176:00 pm -
2 stops16h 34m
Deal found 10/23![Delta logo]()
$474
This Mytrip deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/255:33 pm -
3 stops28h 39m
Tue 12/13:35 pm -
2 stops10h 20m
Deal found 10/22![Multiple Airlines logo]()
$594
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 1/215:40 am -
1 stop9h 46m
Mon 1/251:34 pm -
1 stop11h 25m
Deal found 10/18![American Airlines logo]()
$495
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/610:23 am -
1 stop6h 05m
Sat 2/137:30 pm -
1 stop15h 16m
Deal found 10/22![United Airlines logo]()
$476
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/26:00 am -
1 stop9h 40m
Thu 1/142:10 pm -
1 stop9h 49m
Deal found 10/22![JetBlue logo]()
$433
This Delta deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/116:08 pm -
2 stops17h 57m
Wed 1/133:45 pm -
1 stop8h 31m
Deal found 10/21![Delta logo]()
$481
This American Airlines deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 1/104:16 pm -
2 stops19h 18m
Fri 1/155:29 pm -
2 stops18h 22m
Deal found 10/18![American Airlines logo]()
$499
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated October 23, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated October 23, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:51 am -
1 stop14h 04m
Thu 10/296:00 am -
1 stop29h 00m
Deal found 10/21![Frontier logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:18 pm -
1 stop17h 59m
Tue 11/38:45 am -
1 stop12h 18m
Deal found 10/20![Frontier logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/289:18 pm -
1 stop15h 28m
Wed 11/257:31 am -
1 stop17h 54m
Deal found 10/21![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/297:28 am -
1 stop29h 18m
Tue 11/1011:20 am -
1 stop22h 46m
Deal found 10/23![Frontier logo]()
$239
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:18 pm -
1 stop15h 07m
Sat 11/74:52 pm -
1 stop19h 08m
Deal found 10/21![Frontier logo]()
$232
This CheapOair deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Sat 11/79:59 pm -
1 stop11h 16m
Thu 11/127:00 am -
1 stop8h 16m
Deal found 10/21![Frontier logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/109:18 pm -
1 stop17h 01m
Fri 11/137:00 am -
1 stop13h 02m
Deal found 10/23![Frontier logo]()
$228
This Kiwi.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/116:35 am -
2 stops19h 11m
Fri 11/133:55 pm -
1 stop22h 39m
Deal found 10/21![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/123:21 pm -
2 stops20h 15m
Sun 11/156:00 am -
1 stop30h 00m
Deal found 10/22![Frontier logo]()
$231
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/138:18 pm -
1 stop25h 36m
Sat 11/217:31 am -
1 stop17h 54m
Deal found 10/22![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/153:21 pm -
2 stops20h 15m
Thu 11/193:42 am -
1 stop7h 14m
Deal found 10/22![Frontier logo]()
$235
This JetBlue deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 11/178:00 am -
1 stop7h 18m
Tue 11/243:04 pm -
1 stop9h 45m
Deal found 10/18![JetBlue logo]()
$340
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 October 23, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 23, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/143:21 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:18 pm -
1 stop15h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$101
This Booking.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Mon 11/163:21 pm -
1 stop8h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:18 pm -
1 stop24h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/1312:51 pm -
1 stop11h 16m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/135:47 pm -
1 stop23h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$109
This Cheapflightsfares deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:11 am -
1 stop24h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/19:10 am -
1 stop10h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$112
This Kiwi.com deal was found by Cheapflights users on 10/18. Clicking the “Pick Dates” 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 1/52:06 pm -
1 stop21h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/18![Frontier logo]()
$114
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:33 pm -
1 stop26h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$116
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Mon 11/166:55 pm -
1 stop16h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$150
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/186:05 pm -
1 stop15h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$159
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 October 23, 2026.
Round-trip from | $227 (Kiwi.com) |
|---|---|
One-way from | $99 (Cheapflightsfares) |
Popular in | December |
Cheapest in | May |
Average price | $355 |
Good round-trip deal | $487 or less |
Good one-way deal | $293 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 October 23, 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 12/14
9:10 am-8:37 pm
1 stop10h 27m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$120
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Thu 10/29
9:18 pm-12:46 pm
1 stop15h 28m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Mon 11/23
5:33 pm-1:59 pm
1 stop19h 26m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sun 1/17
5:30 am-8:48 pm
2 stops14h 18m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$151
ClevelandSan Juan
CLE Cleveland Hopkins Intl - SJU San Juan Luis Munoz Marin Intl
CLESJU
Cleveland Hopkins Intl
Sun 11/22
6:15 am-9:49 pm
1 stop14h 34m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$156
ClevelandSanto Domingo
CLE Cleveland Hopkins Intl - SDQ Santo Domingo Las Americas
CLESDQ
Cleveland Hopkins Intl
Mon 2/1
6:45 pm-11:51 am
1 stop16h 06m
Santo Domingo Las Americas
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$160
ClevelandSanto Domingo
CLE Cleveland Hopkins Intl - SDQ Santo Domingo Las Americas
CLESDQ
Cleveland Hopkins Intl
Sun 11/15
8:00 am-4:18 pm
1 stop7h 18m
Santo Domingo Las Americas
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$165
ClevelandOranjestad
CLE Cleveland Hopkins Intl - AUA Oranjestad Reina Beatrix
CLEAUA
Cleveland Hopkins Intl
Wed 12/2
6:55 pm-4:30 pm
1 stop20h 35m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$177
ClevelandSanto Domingo
CLE Cleveland Hopkins Intl - SDQ Santo Domingo Las Americas
CLESDQ
Cleveland Hopkins Intl
Sun 1/31
7:15 am-7:20 pm
1 stop11h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$183
ClevelandSanto Domingo
CLE Cleveland Hopkins Intl - SDQ Santo Domingo Las Americas
CLESDQ
Cleveland Hopkins Intl
Mon 11/16
3:11 pm-2:14 am
2 stops10h 03m
Santo Domingo Las Americas
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$183
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-SDQ
CLE-AUA
CLE-NAS
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-SDQ
CLE-AUA
CLE-NAS
What is the cheapest month to book a flight from Cleveland to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $448). Flying from Cleveland to Caribbean in June is currently the most expensive (average of $578). 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 October 23, 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 often are flights from Cleveland to Caribbean delayed?
About 28% of weekly flights between Cleveland and Caribbean have experienced delays in the past year, with the average delay time being 110 minutes.
What is the most punctual flight time for Cleveland to Caribbean flights?
Historically, flights departing in the evening are less likely to be delayed, whereas flights leaving at night tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Tuesday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Cleveland to Caribbean flights?
Over the last year, Frontier have had the lowest number of delays on this route, with just 28% of flights being delayed.
How far ahead should I book a flight from Cleveland to Caribbean?
Booking 13 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 October 23, 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.
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
Comfort
8.0
Food
7.0
Entertainment
7.4
Boarding
8.1
Crew
8.6
Overall
7.9
Reviews
1 / 20
8.0
ExcellentPatricia,Oct 2026
DAL - TPA
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 October 23, 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 October 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$168 | Average$587 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$187 | Average$472 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$600 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$238 | Average$552 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$252 | Average$577 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$284 | Average$637 | FlexibilityNo cancel fee | On-time63% |