$95+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Apr 9 — Apr 161
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 March 10, 2026.
Explore the most affordable flight options available from Cleveland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 10, 2026.
This eDestinos deal was found by Cheapflights users on 3/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:06 pm
CLE
- SJU
1 stop6h 46m
Frontier
Wed 4/2911:30 am
SJU
- CLE
1 stop22h 33m
Frontier
Deal found 3/5![Frontier logo]()
$208
This Priceline deal was found by Cheapflights users on 3/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
CLE
- SJU
1 stop28h 01m
Frontier
Tue 5/511:07 am
SJU
- CLE
1 stop12h 33m
Frontier
Deal found 3/5![Frontier logo]()
$210
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:37 pm
CLE
- SJU
1 stop8h 14m
Frontier
Mon 4/203:08 am
SJU
- CLE
1 stop20h 32m
Frontier
Deal found 3/6![Frontier logo]()
$211
This Orbitz deal was found by Cheapflights users on 3/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:31 pm
CLE
- SJU
1 stop9h 30m
Frontier
Mon 4/203:08 am
SJU
- CLE
1 stop15h 20m
Frontier
Deal found 3/8![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:31 pm
CLE
- SJU
1 stop9h 30m
Frontier
Fri 4/246:00 am
SJU
- CLE
1 stop17h 55m
Frontier
Deal found 3/7![Frontier logo]()
$215
This Priceline deal was found by Cheapflights users on 3/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/27:07 pm
CLE
- SJU
1 stop28h 22m
Frontier
Sat 5/98:41 am
SJU
- CLE
1 stop25h 22m
Frontier
Deal found 3/5![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:10 pm
CLE
- SJU
1 stop28h 51m
Frontier
Tue 5/123:08 am
SJU
- CLE
1 stop28h 32m
Frontier
Deal found 3/6![Frontier logo]()
$218
This Super.com deal was found by Cheapflights users on 3/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:31 pm
CLE
- SJU
1 stop6h 17m
Frontier
Sat 5/23:21 am
SJU
- CLE
1 stop21h 10m
Frontier
Deal found 3/7![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/81:07 pm
CLE
- SJU
1 stop11h 33m
Frontier
Sat 5/163:08 am
SJU
- CLE
1 stop22h 02m
Frontier
Deal found 3/7![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/34:29 pm
CLE
- SJU
1 stop6h 57m
Frontier
Wed 6/109:15 am
SJU
- CLE
1 stop23h 25m
Frontier
Deal found 3/5![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Sun 4/1211:00 am
CLE
- SJU
1 stop9h 34m
United Airlines
Thu 4/237:20 am
SJU
- CLE
1 stop6h 50m
United Airlines
Deal found 3/6![United Airlines logo]()
$222
This CheapOair deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:20 pm
CLE
- SJU
1 stop10h 41m
Frontier
Sun 5/107:15 am
SJU
- CLE
1 stop17h 41m
Frontier
Deal found 3/10![Frontier logo]()
$223
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 March 10, 2026.
Discover carefully curated flight deals from Cleveland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated March 10, 2026.
This Southwest deal was found by Cheapflights users on 3/5. 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 7/710:40 am
CLE
- SJU
1 stop12h 05m
Southwest
Tue 7/145:00 am
SJU
- CLE
1 stop7h 00m
Southwest
Deal found 3/5![Southwest logo]()
$276
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1911:00 am
CLE
- SJU
2 stops10h 24m
United Airlines
Fri 4/247:40 am
SJU
- CLE
1 stop7h 38m
United Airlines
Deal found 3/8![United Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/227:05 am
CLE
- STT
1 stop7h 43m
Delta
Fri 5/13:59 pm
STT
- CLE
1 stop7h 40m
Delta
Deal found 3/8![Delta logo]()
$290
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1811:51 am
CLE
- SDQ
2 stops17h 38m
Multiple Airlines
Tue 4/216:10 am
SDQ
- CLE
1 stop18h 33m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$384
This Air Canada deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:10 pm
CLE
- NAS
2 stops42h 15m
Air Canada
Tue 4/289:10 pm
NAS
- CLE
1 stop20h 20m
Air Canada
Deal found 3/9![Air Canada logo]()
$413
This American Airlines deal was found by Cheapflights users on 3/6. 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.
Sun 5/247:09 pm
CLE
- STT
1 stop17h 35m
American Airlines
Sat 5/301:34 pm
STT
- CLE
1 stop10h 15m
American Airlines
Deal found 3/6![American Airlines logo]()
$425
This JetBlue deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:00 am
CLE
- NAS
1 stop7h 29m
JetBlue
Mon 6/82:49 pm
NAS
- CLE
1 stop9h 10m
JetBlue
Deal found 3/5![JetBlue logo]()
$442
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
CLE
- STT
1 stop6h 20m
United Airlines
Mon 4/204:45 pm
STT
- CLE
1 stop7h 14m
United Airlines
Deal found 3/8![United Airlines logo]()
$290
This Copa Airlines deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:00 am
CLE
- AUA
2 stops15h 58m
Copa Airlines
Wed 9/91:20 pm
AUA
- CLE
2 stops19h 15m
Copa Airlines
Deal found 3/5![Copa Airlines logo]()
$581
This Southwest deal was found by Cheapflights users on 3/6. 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.
Fri 5/112:40 pm
CLE
- SJU
1 stop11h 00m
Southwest
Sat 5/96:25 am
SJU
- CLE
2 stops9h 45m
Southwest
Deal found 3/6![Southwest logo]()
$296
This Frontier deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/57:05 pm
CLE
- PUJ
2 stops15h 17m
Frontier
Thu 6/113:32 pm
PUJ
- CLE
2 stops17h 08m
Frontier
Deal found 3/5![Frontier logo]()
$618
This Delta deal was found by Cheapflights users on 3/7. 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.
Thu 3/196:00 am
CLE
- STT
1 stop8h 45m
Delta
Wed 3/2512:49 pm
STT
- CLE
1 stop11h 40m
Delta
Deal found 3/7![Delta logo]()
$315
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:15 pm
CLE
- SJU
2 stops11h 35m
United Airlines
Wed 4/221:00 am
SJU
- CLE
2 stops12h 19m
United Airlines
Deal found 3/8![United Airlines logo]()
$312
This Southwest deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/161:05 pm
CLE
- SJU
1 stop8h 25m
Southwest
Tue 7/219:50 am
SJU
- CLE
2 stops9h 50m
Southwest
Deal found 3/5![Southwest logo]()
$346
This United Airlines deal was found by Cheapflights users on 3/6. 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 5/116:00 am
CLE
- MBJ
1 stop10h 10m
United Airlines
Sat 5/164:12 pm
MBJ
- CLE
1 stop6h 47m
United Airlines
Deal found 3/6![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/97:05 am
CLE
- MBJ
1 stop9h 29m
Delta
Tue 5/122:21 pm
MBJ
- CLE
1 stop6h 22m
Delta
Deal found 3/9![Delta logo]()
$372
This FlightHub deal was found by Cheapflights users on 3/7. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:33 pm
CLE
- SXM
1 stop25h 56m
Multiple Airlines
Thu 6/43:05 pm
SXM
- CLE
1 stop22h 56m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/13:35 pm
CLE
- SJU
1 stop8h 05m
Southwest
Thu 8/65:00 am
SJU
- CLE
2 stops10h 10m
Southwest
Deal found 3/9![Southwest logo]()
$346
This JetBlue deal was found by Cheapflights users on 3/7. 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.
Sat 4/256:00 am
CLE
- NAS
1 stop6h 42m
JetBlue
Tue 4/281:47 pm
NAS
- CLE
1 stop10h 03m
JetBlue
Deal found 3/7![JetBlue logo]()
$442
This American Airlines deal was found by Cheapflights users on 3/6. 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 5/96:00 am
CLE
- SXM
2 stops9h 32m
American Airlines
Sat 5/1612:41 pm
SXM
- CLE
1 stop11h 18m
American Airlines
Deal found 3/6![American Airlines logo]()
$448
This Delta deal was found by Cheapflights users on 3/5. 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.
Tue 4/145:50 am
CLE
- AUA
1 stop8h 20m
Delta
Tue 4/211:55 pm
AUA
- CLE
1 stop9h 44m
Delta
Deal found 3/5![Delta logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:31 pm
CLE
- SDQ
1 stop7h 07m
Multiple Airlines
Sun 3/292:52 am
SDQ
- CLE
2 stops33h 14m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/25:35 am
CLE
- MBJ
1 stop8h 15m
United Airlines
Wed 5/64:12 pm
MBJ
- CLE
1 stop16h 28m
United Airlines
Deal found 3/9![United Airlines logo]()
$352
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/145:45 pm
CLE
- SJU
1 stop6h 55m
Southwest
Mon 6/225:00 am
SJU
- CLE
2 stops10h 20m
Southwest
Deal found 3/8![Southwest logo]()
$376
This JetBlue deal was found by Cheapflights users on 3/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:00 am
CLE
- PLS
1 stop8h 10m
JetBlue
Thu 4/163:20 pm
PLS
- CLE
1 stop8h 30m
JetBlue
Deal found 3/8![JetBlue logo]()
$463
This American Airlines deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:41 pm
CLE
- SXM
2 stops19h 01m
American Airlines
Mon 6/221:40 pm
SXM
- CLE
1 stop9h 59m
American Airlines
Deal found 3/10![American Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:15 pm
CLE
- SJU
2 stops11h 35m
United Airlines
Wed 4/151:00 am
SJU
- CLE
1 stop9h 14m
United Airlines
Deal found 3/8![United Airlines logo]()
$359
This Delta deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/174:54 pm
CLE
- SJU
1 stop6h 18m
Delta
Tue 4/2112:55 pm
SJU
- CLE
1 stop11h 39m
Delta
Deal found 3/8![Delta logo]()
$401
This Travelocity deal was found by Cheapflights users on 3/7. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/66:00 am
CLE
- PLS
1 stop7h 27m
Multiple Airlines
Sat 6/132:10 pm
PLS
- CLE
1 stop23h 51m
Multiple Airlines
Deal found 3/7![Multiple Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 3/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/94:15 pm
CLE
- SJU
2 stops8h 00m
Southwest
Fri 6/125:15 pm
SJU
- CLE
1 stop7h 00m
Southwest
Deal found 3/8![Southwest logo]()
$396
Last-minute flights from Cleveland to CaribbeanDiscover last-minute flight deals from Cleveland to Caribbean. Data last updated March 10, 2026 and is based on user searches.
Discover last-minute flight deals from Cleveland to Caribbean. Data last updated March 10, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 3/5. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:06 pm
CLE
- SJU
1 stop6h 46m
Frontier
Wed 4/2911:30 am
SJU
- CLE
1 stop22h 33m
Frontier
Deal found 3/5![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 3/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/85:30 am
CLE
- SJU
1 stop14h 20m
Multiple Airlines
Tue 4/283:08 am
SJU
- CLE
1 stop20h 51m
Multiple Airlines
Deal found 3/5![Multiple Airlines logo]()
$226
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:37 pm
CLE
- SJU
1 stop8h 14m
Frontier
Mon 4/203:08 am
SJU
- CLE
1 stop20h 32m
Frontier
Deal found 3/6![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 3/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:37 pm
CLE
- SJU
1 stop8h 14m
Frontier
Sat 5/305:56 pm
SJU
- CLE
1 stop28h 06m
Frontier
Deal found 3/6![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 3/6. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/114:37 pm
CLE
- SJU
1 stop8h 14m
Frontier
Sun 4/196:30 am
SJU
- CLE
1 stop17h 29m
Frontier
Deal found 3/6![Frontier logo]()
$224
This United Airlines deal was found by Cheapflights users on 3/6. 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.
Sun 4/126:10 am
CLE
- SJU
1 stop9h 32m
United Airlines
Thu 4/237:20 am
SJU
- CLE
1 stop6h 50m
United Airlines
Deal found 3/6![United Airlines logo]()
$222
This Trip.com deal was found by Cheapflights users on 3/5. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:46 pm
CLE
- SJU
1 stop9h 15m
Frontier
Sun 4/196:30 am
SJU
- CLE
1 stop17h 29m
Frontier
Deal found 3/5![Frontier logo]()
$221
This Orbitz deal was found by Cheapflights users on 3/8. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:31 pm
CLE
- SJU
1 stop9h 30m
Frontier
Mon 4/203:08 am
SJU
- CLE
1 stop15h 20m
Frontier
Deal found 3/8![Frontier logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/8. 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.
Tue 4/212:46 pm
CLE
- STT
1 stop19h 08m
Multiple Airlines
Wed 4/2910:49 am
STT
- CLE
1 stop13h 10m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$288
This Super.com deal was found by Cheapflights users on 3/7. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:31 pm
CLE
- SJU
1 stop6h 17m
Frontier
Sat 5/23:21 am
SJU
- CLE
1 stop21h 10m
Frontier
Deal found 3/7![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 4/259:05 pm
CLE
- STT
1 stop12h 49m
Multiple Airlines
Wed 4/2910:49 am
STT
- CLE
1 stop13h 10m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$289
This Priceline deal was found by Cheapflights users on 3/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/3010:00 pm
CLE
- SJU
1 stop28h 01m
Frontier
Tue 5/511:07 am
SJU
- CLE
1 stop12h 33m
Frontier
Deal found 3/5![Frontier logo]()
$210
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 March 10, 2026.
Search for one-way flight options from Cleveland to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 10, 2026.
This Super.com deal was found by Cheapflights users on 3/5. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/248:09 pm
CLE
- SJU
1 stop15h 01m
Frontier
Deal found 3/5![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 3/6. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:31 pm
CLE
- SJU
1 stop9h 30m
Frontier
Deal found 3/6![Frontier logo]()
$96
This Trip.com deal was found by Cheapflights users on 3/6. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/234:55 pm
CLE
- SJU
1 stop8h 26m
Frontier
Deal found 3/6![Frontier logo]()
$100
This Expedia deal was found by Cheapflights users on 3/6. 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.
Tue 3/317:16 pm
CLE
- SJU
1 stop6h 47m
Frontier
Deal found 3/6![Frontier logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:29 pm
CLE
- SJU
1 stop29h 00m
Frontier
Deal found 3/9![Frontier logo]()
$104
This eDestinos deal was found by Cheapflights users on 3/6. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/188:44 pm
CLE
- SJU
1 stop16h 07m
Frontier
Deal found 3/6![Frontier logo]()
$106
This eDestinos deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:28 pm
CLE
- SJU
1 stop7h 31m
Frontier
Deal found 3/10![Frontier logo]()
$107
This eDestinos deal was found by Cheapflights users on 3/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/307:08 pm
CLE
- SJU
1 stop15h 19m
Frontier
Deal found 3/8![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 5/316:15 am
CLE
- SJU
1 stop18h 32m
Frontier
Deal found 3/6![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 3/6. 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 4/2510:44 am
CLE
- SJU
1 stop11h 21m
American Airlines
Deal found 3/6![American Airlines logo]()
$111
This Cheapflightsfares deal was found by Cheapflights users on 3/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/226:31 pm
CLE
- SDQ
1 stop7h 07m
Spirit Airlines
Deal found 3/5![Spirit Airlines logo]()
$119
This Air Canada deal was found by Cheapflights users on 3/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:10 pm
CLE
- NAS
1 stop18h 45m
Air Canada
Deal found 3/10![Air Canada logo]()
$135
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 March 10, 2026.
Round-trip from | $208 (eDestinos) |
|---|---|
One-way from | $95 (Super.com) |
Popular in | December |
Cheapest in | May |
Average price | $352 |
Good round-trip deal | $499 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 March 10, 2026.
Use the filters below to find and compare flights from Cleveland to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Tue 7/7
10:40 am-10:45 pm
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Tue 7/14
5:00 am-12:00 pm
1 stop7h 00m
$276
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 4/19
11:00 am-9:24 pm
2 stops10h 24m
San Juan Luis Munoz Marin Intl
Fri 4/24
7:40 am-3:18 pm
1 stop7h 38m
$277
ClevelandSaint Thomas Island
CLE - STT
CLESTT
Cleveland Hopkins Intl
Wed 4/22
7:05 am-2:48 pm
1 stop7h 43m
Saint Thomas Island Cyril E King
Fri 5/1
3:59 pm-11:39 pm
1 stop7h 40m
$290
Quickest round-trip
ClevelandSaint Thomas Island
CLE - STT
CLESTT
Cleveland Hopkins Intl
Wed 4/15
6:00 am-12:20 pm
1 stop6h 20m
Saint Thomas Island Cyril E King
Mon 4/20
4:45 pm-11:59 pm
1 stop7h 14m
$290
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Fri 5/1
12:40 pm-11:40 pm
1 stop11h 00m
San Juan Luis Munoz Marin Intl
Sat 5/9
6:25 am-4:10 pm
2 stops9h 45m
$296
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 4/20
12:15 pm-11:50 pm
2 stops11h 35m
San Juan Luis Munoz Marin Intl
Wed 4/22
1:00 am-1:19 pm
2 stops12h 19m
$312
ClevelandSaint Thomas Island
CLE - STT
CLESTT
Cleveland Hopkins Intl
Thu 3/19
6:00 am-2:45 pm
1 stop8h 45m
Saint Thomas Island Cyril E King
Wed 3/25
12:49 pm-12:29 am
1 stop11h 40m
$315
ClevelandMontego Bay
CLE - MBJ
CLEMBJ
Cleveland Hopkins Intl
Mon 5/11
6:00 am-3:10 pm
1 stop10h 10m
Montego Bay Sangster Intl
Sat 5/16
4:12 pm-11:59 pm
1 stop6h 47m
$332
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Thu 7/16
1:05 pm-9:30 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Tue 7/21
9:50 am-7:40 pm
2 stops9h 50m
$346
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sat 8/1
3:35 pm-11:40 pm
1 stop8h 05m
San Juan Luis Munoz Marin Intl
Thu 8/6
5:00 am-3:10 pm
2 stops10h 10m
$346
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-STT
CLE-SDQ
CLE-NAS
CLE-AUA
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-STT
CLE-SDQ
CLE-NAS
What is the cheapest month to book a flight from Cleveland to Caribbean?
Currently, November is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $103). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $199). 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 March 10, 2026.
It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 73% on the flight price compared to flying at noon, which is usually more expensive.
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 March 10, 2026.
See what other customers who have flown with Southwest,Delta, andUnited Airlines from Cleveland to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - HNL
Overall
8.0
Crew
8.6
Comfort
8.0
Food
7.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentAnonymous,Mar 2026
KOA - 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.
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 March 10, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Cleveland to Caribbean flights
Consider these flights traveling from Cleveland to Caribbean.
Top 7 airlines flying from Cleveland to Caribbean
Discover the top 7 airlines that operate flights from Cleveland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$103 | Average$513 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$137 | Average$386 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$158 | Average$430 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$160 | Average$500 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$219 | Average$577 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$553 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$246 | Average$587 | FlexibilityNo cancel fee | On-time63% |