$131+ 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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Aug 26 — Sep 21
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 July 27, 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 July 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:45 am
CLE
- SJU
2 stops18h 11m
Frontier
Thu 8/275:15 pm
SJU
- CLE
1 stop19h 29m
Frontier
Deal found 7/23![Frontier logo]()
$275
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/212:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/285:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/22![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:33 pm
CLE
- SJU
1 stop30h 08m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Thu 8/205:15 pm
SJU
- CLE
2 stops42h 40m
Frontier
Deal found 7/24![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:10 am
CLE
- SJU
1 stop8h 01m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/23![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:07 pm
CLE
- SJU
1 stop7h 36m
Frontier
Sat 8/295:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/23![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/215:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:17 pm
CLE
- SJU
1 stop7h 24m
Frontier
Mon 10/129:49 pm
SJU
- CLE
1 stop11h 13m
Frontier
Deal found 7/23![Frontier logo]()
$286
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/147:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Wed 9/232:35 pm
NAS
- CLE
1 stop7h 16m
United Airlines
Deal found 7/24![United Airlines logo]()
$358
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Mon 8/317:30 pm
CLE
- NAS
1 stop15h 58m
United Airlines
Thu 9/312:35 pm
NAS
- CLE
1 stop9h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$362
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 July 27, 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 July 27, 2026.
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Mon 8/317:30 pm
CLE
- NAS
1 stop15h 58m
United Airlines
Thu 9/312:35 pm
NAS
- CLE
1 stop9h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am
CLE
- SJU
1 stop10h 49m
Delta
Fri 10/95:43 pm
SJU
- CLE
1 stop7h 05m
Delta
Deal found 7/22![Delta logo]()
$364
This Southwest deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 am
CLE
- SJU
2 stops10h 15m
Southwest
Mon 9/286:30 am
SJU
- CLE
2 stops10h 15m
Southwest
Deal found 7/25![Southwest logo]()
$382
This JetBlue deal was found by Cheapflights users on 7/22. 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.
Thu 9/107:00 am
CLE
- SDQ
1 stop7h 49m
JetBlue
Wed 9/163:59 pm
SDQ
- CLE
1 stop7h 33m
JetBlue
Deal found 7/22![JetBlue logo]()
$405
This Air Canada deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:00 pm
CLE
- SXM
1 stop22h 00m
Air Canada
Sun 10/253:45 pm
SXM
- CLE
1 stop26h 32m
Air Canada
Deal found 7/24![Air Canada logo]()
$424
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 8/216:15 am
CLE
- STT
1 stop6h 38m
American Airlines
Fri 8/284:42 pm
STT
- CLE
2 stops19h 18m
American Airlines
Deal found 7/22![American Airlines logo]()
$432
This Expedia deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:50 am
CLE
- MBJ
1 stop9h 28m
Multiple Airlines
Thu 8/201:32 pm
MBJ
- CLE
1 stop7h 59m
Multiple Airlines
Deal found 7/25![Multiple Airlines logo]()
$505
This Copa Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/910:52 am
CLE
- AUA
2 stops27h 51m
Copa Airlines
Sun 9/137:10 am
AUA
- CLE
2 stops26h 31m
Copa Airlines
Deal found 7/24![Copa Airlines logo]()
$672
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:30 am
CLE
- SJU
1 stop6h 46m
Delta
Sat 9/262:30 pm
SJU
- CLE
1 stop6h 28m
Delta
Deal found 7/22![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
CLE
- SJU
1 stop7h 44m
United Airlines
Sat 9/121:00 am
SJU
- CLE
2 stops12h 08m
United Airlines
Deal found 7/25![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:35 am
CLE
- SJU
2 stops8h 55m
Southwest
Wed 9/98:20 am
SJU
- CLE
2 stops10h 10m
Southwest
Deal found 7/24![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1011:22 am
CLE
- SJU
1 stop10h 37m
Delta
Sat 10/177:00 am
SJU
- CLE
1 stop9h 40m
Delta
Deal found 7/23![Delta logo]()
$364
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:07 pm
CLE
- SJU
1 stop7h 43m
United Airlines
Fri 10/161:00 am
SJU
- CLE
2 stops12h 06m
United Airlines
Deal found 7/27![United Airlines logo]()
$374
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:00 am
CLE
- SDQ
1 stop7h 49m
JetBlue
Sat 9/192:29 pm
SDQ
- CLE
1 stop9h 03m
JetBlue
Deal found 7/23![JetBlue logo]()
$414
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/131:45 pm
CLE
- SJU
2 stops10h 10m
Southwest
Sun 9/205:00 am
SJU
- CLE
2 stops9h 25m
Southwest
Deal found 7/27![Southwest logo]()
$395
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 9/106:32 am
CLE
- SDQ
2 stops12h 02m
American Airlines
Wed 9/164:20 pm
SDQ
- CLE
1 stop7h 26m
American Airlines
Deal found 7/22![American Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 7/23. 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.
Wed 10/76:00 am
CLE
- NAS
1 stop5h 51m
Delta
Tue 10/1312:55 pm
NAS
- CLE
1 stop10h 07m
Delta
Deal found 7/23![Delta logo]()
$364
This JetBlue deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/127:00 am
CLE
- SDQ
1 stop6h 19m
JetBlue
Wed 9/163:59 pm
SDQ
- CLE
1 stop7h 33m
JetBlue
Deal found 7/23![JetBlue logo]()
$414
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Thu 9/37:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Sun 9/612:35 pm
NAS
- CLE
1 stop7h 31m
United Airlines
Deal found 7/22![United Airlines logo]()
$388
This Southwest deal was found by Cheapflights users on 7/22. 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.
Wed 10/216:15 am
CLE
- SJU
2 stops11h 30m
Southwest
Sun 10/256:00 am
SJU
- CLE
2 stops15h 20m
Southwest
Deal found 7/22![Southwest logo]()
$398
This Delta deal was found by Cheapflights users on 7/23. 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 10/67:05 am
CLE
- NAS
1 stop4h 46m
Delta
Tue 10/1312:55 pm
NAS
- CLE
1 stop10h 07m
Delta
Deal found 7/23![Delta logo]()
$364
This Air Canada deal was found by Cheapflights users on 7/22. 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.
Thu 11/196:55 pm
CLE
- MBJ
2 stops18h 30m
Air Canada
Mon 11/236:20 pm
MBJ
- CLE
1 stop23h 57m
Air Canada
Deal found 7/22![Air Canada logo]()
$485
This American Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/107:38 pm
CLE
- STT
1 stop17h 01m
American Airlines
Sat 10/173:46 pm
STT
- CLE
2 stops19h 42m
American Airlines
Deal found 7/24![American Airlines logo]()
$452
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Wed 9/27:30 pm
CLE
- NAS
1 stop15h 58m
United Airlines
Sat 9/512:35 pm
NAS
- CLE
1 stop7h 31m
United Airlines
Deal found 7/22![United Airlines logo]()
$388
This JetBlue deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:00 am
CLE
- SXM
1 stop7h 00m
JetBlue
Fri 9/253:05 pm
SXM
- CLE
1 stop8h 27m
JetBlue
Deal found 7/27![JetBlue logo]()
$427
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:00 am
CLE
- SJU
2 stops10h 25m
Southwest
Sun 9/275:00 am
SJU
- CLE
2 stops9h 25m
Southwest
Deal found 7/27![Southwest logo]()
$399
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/46:00 pm
CLE
- SXM
1 stop17h 15m
Delta
Fri 1/154:05 pm
SXM
- CLE
1 stop18h 35m
Delta
Deal found 7/26![Delta logo]()
$384
This American Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 8/286:00 am
CLE
- STT
2 stops9h 52m
American Airlines
Wed 9/21:49 pm
STT
- CLE
2 stops20h 59m
American Airlines
Deal found 7/22![American Airlines logo]()
$468
This Booking.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:55 pm
CLE
- SXM
2 stops42h 45m
Air Canada
Sun 11/14:45 pm
SXM
- CLE
1 stop26h 32m
Air Canada
Deal found 7/24![Air Canada logo]()
$516
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 8/287:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Fri 9/412:35 pm
NAS
- CLE
1 stop9h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$388
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated July 27, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated July 27, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:33 pm
CLE
- SJU
1 stop30h 08m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$278
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Sat 8/225:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/26![Frontier logo]()
$277
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/167:45 am
CLE
- SJU
1 stop8h 26m
Frontier
Thu 8/205:15 pm
SJU
- CLE
2 stops42h 40m
Frontier
Deal found 7/24![Frontier logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/164:28 pm
CLE
- SJU
1 stop8h 00m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/26![Frontier logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/182:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/215:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/24![Frontier logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/192:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Wed 9/26:35 am
SJU
- CLE
1 stop16h 54m
Frontier
Deal found 7/23![Frontier logo]()
$286
This Kiwi.com deal was found by Cheapflights users on 7/22. 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.
Fri 8/212:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Fri 8/285:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/22![Frontier logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:10 am
CLE
- SJU
1 stop8h 01m
Frontier
Tue 8/258:57 pm
SJU
- CLE
1 stop10h 59m
Frontier
Deal found 7/23![Frontier logo]()
$280
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/225:07 pm
CLE
- SJU
1 stop7h 36m
Frontier
Sat 8/295:37 pm
SJU
- CLE
2 stops28h 54m
Frontier
Deal found 7/23![Frontier logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/246:45 am
CLE
- SJU
2 stops18h 11m
Frontier
Thu 8/275:15 pm
SJU
- CLE
1 stop19h 29m
Frontier
Deal found 7/23![Frontier logo]()
$275
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/255:26 am
CLE
- NAS
1 stop6h 25m
Delta
Tue 9/13:22 pm
NAS
- CLE
1 stop9h 07m
Delta
Deal found 7/26![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Mon 8/317:30 pm
CLE
- NAS
1 stop15h 58m
United Airlines
Thu 9/312:35 pm
NAS
- CLE
1 stop9h 16m
United Airlines
Deal found 7/22![United Airlines logo]()
$362
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 July 27, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 27, 2026.
This Delta deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:00 am
CLE
- NAS
1 stop5h 51m
Delta
Deal found 7/24![Delta logo]()
$131
This United Airlines deal was found by Cheapflights users on 7/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:00 am
CLE
- NAS
1 stop6h 33m
United Airlines
Deal found 7/24![United Airlines logo]()
$132
This Travelocity deal was found by Cheapflights users on 7/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/510:00 am
CLE
- NAS
2 stops27h 35m
Air Canada
Deal found 7/23![Air Canada logo]()
$150
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:45 pm
CLE
- SJU
2 stops25h 05m
Frontier
Deal found 7/26![Frontier logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:07 pm
CLE
- SJU
1 stop14h 46m
Frontier
Deal found 7/26![Frontier logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/252:04 pm
CLE
- SJU
1 stop10h 52m
Frontier
Deal found 7/23![Frontier logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:10 am
CLE
- SJU
1 stop15h 28m
Frontier
Deal found 7/23![Frontier logo]()
$154
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/126:00 am
CLE
- NAS
1 stop7h 53m
Delta
Deal found 7/23![Delta logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 7/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/35:15 pm
CLE
- SJU
2 stops31h 41m
Frontier
Deal found 7/25![Frontier logo]()
$156
This American Airlines deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/124:38 pm
CLE
- NAS
2 stops17h 04m
American Airlines
Deal found 7/23![American Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/249:10 pm
CLE
- SJU
1 stop16h 24m
Frontier
Deal found 7/26![Frontier logo]()
$157
This Delta deal was found by Cheapflights users on 7/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:09 am
CLE
- NAS
1 stop10h 30m
Delta
Deal found 7/23![Delta logo]()
$157
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 July 27, 2026.
Round-trip from | $275 (Kiwi.com) |
|---|---|
One-way from | $131 (Delta) |
Popular in | December |
Cheapest in | May |
Average price | $402 |
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 July 27, 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
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Mon 8/31
7:30 pm-11:28 am
1 stop15h 58m
Nassau Intl
Thu 9/3
12:35 pm-9:51 pm
1 stop9h 16m
$362
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 10/4
6:00 am-4:49 pm
1 stop10h 49m
San Juan Luis Munoz Marin Intl
Fri 10/9
5:43 pm-12:48 am
1 stop7h 05m
$364
Quickest round-trip
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 9/19
6:30 am-1:16 pm
1 stop6h 46m
San Juan Luis Munoz Marin Intl
Sat 9/26
2:30 pm-8:58 pm
1 stop6h 28m
$364
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 10/10
11:22 am-9:59 pm
1 stop10h 37m
San Juan Luis Munoz Marin Intl
Sat 10/17
7:00 am-4:40 pm
1 stop9h 40m
$364
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Wed 10/7
6:00 am-11:51 am
1 stop5h 51m
Nassau Intl
Tue 10/13
12:55 pm-11:02 pm
1 stop10h 07m
$364
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Tue 10/6
7:05 am-11:51 am
1 stop4h 46m
Nassau Intl
Tue 10/13
12:55 pm-11:02 pm
1 stop10h 07m
$364
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 9/9
7:00 am-2:44 pm
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-1:08 pm
2 stops12h 08m
$369
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 10/10
4:07 pm-11:50 pm
1 stop7h 43m
San Juan Luis Munoz Marin Intl
Fri 10/16
1:00 am-1:06 pm
2 stops12h 06m
$374
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 9/25
6:40 am-4:55 pm
2 stops10h 15m
San Juan Luis Munoz Marin Intl
Mon 9/28
6:30 am-4:45 pm
2 stops10h 15m
$382
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Mon 1/4
6:00 pm-12:15 pm
1 stop17h 15m
Simpson Bay Princess Juliana
Fri 1/15
4:05 pm-9:40 am
1 stop18h 35m
$384
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-NAS
CLE-SJU
CLE-AUA
CLE-PUJ
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-NAS
CLE-SJU
CLE-AUA
CLE-PUJ
What is the cheapest month to book a flight from Cleveland to Caribbean?
Currently, October is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $434). Flying from Cleveland to Caribbean in June is currently the most expensive (average of $580). 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 July 27, 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 July 27, 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
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Comfort
8.0
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Crew
8.6
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
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 July 27, 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 July 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$542 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$151 | Average$389 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$184 | Average$578 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$186 | Average$473 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$225 | Average$589 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$228 | Average$540 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$259 | Average$614 | FlexibilityNo cancel fee | On-time63% |