$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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jan 14 — Jan 211
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 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 December 15, 2025.
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 December 15, 2025.
This eDestinos deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/226:59 pmCLE - SJU
1 stop6h 51mFrontier
Thu 12/253:21 pmSJU - CLE
1 stop10h 15mFrontier
Deal found 12/14![Frontier logo]()
$239
This Expedia deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2011:26 amCLE - SJU
1 stop11h 49mFrontier
Sat 1/108:15 amSJU - CLE
1 stop26h 20mFrontier
Deal found 12/13![Frontier logo]()
$240
This CheapOair deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1711:19 amCLE - SJU
1 stop20h 39mFrontier
Sat 1/108:15 amSJU - CLE
1 stop26h 20mFrontier
Deal found 12/13![Frontier logo]()
$241
This Mytrip deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:54 amCLE - SJU
1 stop12h 51mMultiple Airlines
Sun 12/213:55 amSJU - CLE
1 stop7h 26mMultiple Airlines
Deal found 12/14![Multiple Airlines logo]()
$243
This CheapOair deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/244:48 pmCLE - SJU
1 stop22h 11mFrontier
Sat 12/273:54 amSJU - CLE
1 stop21h 42mFrontier
Deal found 12/14![Frontier logo]()
$250
This eDestinos deal was found by Cheapflights users on 12/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/215:22 pmCLE - SJU
1 stop14h 17mFrontier
Sun 12/283:55 amSJU - CLE
1 stop14h 55mFrontier
Deal found 12/12![Frontier logo]()
$261
This Frontier deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/157:14 amCLE - SJU
1 stop6h 57mFrontier
Wed 12/244:16 pmSJU - CLE
1 stop7h 57mFrontier
Deal found 12/13![Frontier logo]()
$264
This CheapOair deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/177:17 pmCLE - SJU
1 stop17h 17mFrontier
Sat 12/2010:28 amSJU - CLE
1 stop11h 23mFrontier
Deal found 12/13![Frontier logo]()
$265
This Priceline deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:48 pmCLE - SJU
1 stop24h 39mFrontier
Tue 1/133:47 pmSJU - CLE
1 stop28h 57mFrontier
Deal found 12/14![Frontier logo]()
$266
This Mytrip deal was found by Cheapflights users on 12/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:54 amCLE - SJU
1 stop12h 51mMultiple Airlines
Sun 12/219:49 amSJU - CLE
1 stop15h 47mMultiple Airlines
Deal found 12/14![Multiple Airlines logo]()
$269
This Frontier deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/206:20 amCLE - NAS
1 stop9h 47mFrontier
Sat 12/275:22 pmNAS - CLE
1 stop5h 56mFrontier
Deal found 12/13![Frontier logo]()
$331
This Expedia deal was found by Cheapflights users on 12/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/236:00 amCLE - MBJ
1 stop8h 29mFrontier
Mon 12/2910:14 amMBJ - CLE
1 stop13h 13mFrontier
Deal found 12/13![Frontier logo]()
$351
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 December 15, 2025.
Round-trip from | $228 (Kiwi.com) |
|---|---|
One-way from | $95 (Frontier) |
Popular in | December |
Cheapest in | May |
Average price | $489 |
Good round-trip deal | $333 or less |
Good one-way deal | $175 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 December 15, 2025.
Use the filters below to find and compare flights from Cleveland to Caribbean that are best for you.
Fly from
Cleveland
Fly to
Caribbean
Route
Depart
Return
Price
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Wed 1/28
8:10 am-5:17 pm
1 stop8h 07m
San Juan Luis Munoz Marin Intl
Fri 2/6
6:27 pm-12:36 am
1 stop7h 09m
$245
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Sun 1/18
6:30 am-2:10 pm
1 stop30h 40m
Simpson Bay Princess Juliana
Fri 1/23
3:15 pm-10:44 pm
1 stop8h 29m
$283
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Thu 1/8
7:01 pm-2:10 pm
1 stop18h 09m
Simpson Bay Princess Juliana
Mon 1/12
3:15 pm-11:11 pm
2 stops32h 56m
$304
ClevelandSimpson Bay
CLE - SXM
CLESXM
Cleveland Hopkins Intl
Thu 1/22
3:44 pm-2:10 pm
1 stop21h 26m
Simpson Bay Princess Juliana
Mon 1/26
3:15 pm-1:44 pm
2 stops23h 29m
$309
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 1/25
6:00 pm-6:11 am
1 stop11h 11m
San Juan Luis Munoz Marin Intl
Thu 2/5
2:05 am-4:51 pm
2 stops15h 46m
$315
ClevelandNassau
CLE - NAS
CLENAS
Cleveland Hopkins Intl
Sat 2/7
7:10 am-5:09 pm
1 stop9h 59m
Nassau Intl
Sat 2/14
3:35 pm-11:15 pm
1 stop7h 40m
$315
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Mon 2/2
8:49 am-12:36 am
2 stops14h 47m
San Juan Luis Munoz Marin Intl
Thu 2/5
2:05 am-4:51 pm
2 stops15h 46m
$315
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 2/15
6:21 pm-6:11 am
1 stop10h 50m
San Juan Luis Munoz Marin Intl
Wed 3/4
8:10 am-8:29 pm
2 stops13h 19m
$315
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 1/11
4:07 pm-6:11 am
2 stops13h 04m
San Juan Luis Munoz Marin Intl
Thu 1/15
2:05 am-8:22 am
1 stop7h 17m
$315
ClevelandSan Juan
CLE - SJU
CLESJU
Cleveland Hopkins Intl
Sun 1/25
7:20 am-3:40 pm
1 stop7h 20m
San Juan Luis Munoz Marin Intl
Fri 1/30
2:05 am-3:26 pm
2 stops14h 21m
$315
Showing 1-10 of 60 results
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.
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
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 $209). 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 December 15, 2025.
It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.
What is the cheapest day to fly from Cleveland to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Cleveland to Caribbean. Price data was last updated on December 16, 2024.
Travelers seeking maximum savings on their Cleveland to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 December 15, 2025.
See what other customers who have flown with Southwest, Delta, and United 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
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Overall
7.9
Comfort
8.0
Entertainment
7.5
Food
7.0
Boarding
8.1
Crew
8.6
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
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 for Cleveland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
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 December 15, 2025.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$146 | Average$388 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$155 | Average$409 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$163 | Average$543 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$193 | Average$572 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$210 | Average$591 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$225 | Average$586 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$264 | Average$629 | FlexibilityNo cancel fee | On-time63% |