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$97+ 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 5/21. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Apr 22 — Apr 291
Tue 4/22
Tue 4/29
1 adult, Economy
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Cheap flight deals from Cleveland to Caribbean

Keep the following information in mind while searching for Cleveland to Caribbean flight deals. Data was last updated April 17, 2025.

Round-trip from

$190
(Cheapflightsfares)

One-way from

$97
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$248

Good round-trip deal

$194 or less

Good one-way deal

$97 or less
From Cleveland Hopkins Intl to Caribbean
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One-way flight from Cleveland Hopkins Intl to Caribbean
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Highest demand for flights based on searches. 20% potential increase in price ($80 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Cleveland Hopkins Intl to Caribbean.
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Price to beat on a one-way flight from Cleveland Hopkins Intl to Caribbean.
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Find flight deals from Cleveland to Caribbean

Cheapest flights from Cleveland to Caribbean
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 April 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Wed 4/305:00 pmCLE - SJU
Nonstop4h 12mFrontier
Wed 4/3012:05 amSJU - CLE
Nonstop4h 56mFrontier
Deal found 4/15$190
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/49:30 pmCLE - SJU
Nonstop4h 21mMultiple Airlines
Fri 5/98:12 pmSJU - CLE
1 stop15h 34mMultiple Airlines
Deal found 4/17$205
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 4/261:33 pmCLE - SJU
1 stop15h 27mAmerican Airlines
Sat 5/35:30 amSJU - CLE
1 stop12h 52mAmerican Airlines
Deal found 4/17$207
This Delta deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 4/2712:31 pmCLE - SJU
1 stop11h 17mDelta
Fri 5/25:11 pmSJU - CLE
1 stop7h 32mDelta
Deal found 4/16$217
This CheapOair deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Thu 7/248:29 pmCLE - STT
1 stop20h 00mFrontier
Mon 7/285:14 pmSTT - CLE
1 stop19h 26mFrontier
Deal found 4/17$219
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/311:06 amCLE - SJU
2 stops12h 51mUnited Airlines
Wed 5/77:25 amSJU - CLE
1 stop6h 39mUnited Airlines
Deal found 4/16$221
This Mytrip deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/57:18 pmCLE - SJU
2 stops24h 22mSpirit Airlines
Fri 5/98:12 pmSJU - CLE
1 stop15h 34mSpirit Airlines
Deal found 4/16$257
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Sat 6/77:10 pmCLE - STT
1 stop14h 47mSpirit Airlines
Wed 6/1110:52 amSTT - CLE
1 stop25h 03mSpirit Airlines
Deal found 4/17$272
This Booking.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/298:31 pmCLE - SDQ
1 stop20h 56mFrontier
Sat 5/3112:27 pmSDQ - CLE
1 stop24h 02mFrontier
Deal found 4/17$294
This American Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 8/256:26 amCLE - STT
1 stop6h 24mAmerican Airlines
Fri 8/295:25 pmSTT - CLE
1 stop6h 36mAmerican Airlines
Deal found 4/17$351
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 10/177:55 amCLE - STX
1 stop8h 23mSpirit Airlines
Sat 10/255:13 pmSTX - CLE
1 stop7h 06mSpirit Airlines
Deal found 4/17$352
This FlightHub deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Sat 7/198:29 pmCLE - STX
1 stop20h 11mMultiple Airlines
Sat 7/265:13 pmSTX - CLE
1 stop7h 06mMultiple Airlines
Deal found 4/17$370

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 April 17, 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 4/30

5:00 pm-9:12 pm

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

Wed 4/30

12:05 am-5:01 am

Nonstop4h 56m

$190

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 5/4

9:30 pm-1:51 am

Nonstop4h 21m

San Juan Luis Munoz Marin Intl

Fri 5/9

8:12 pm-11:46 am

1 stop15h 34m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/26

1:33 pm-5:00 am

1 stop15h 27m

San Juan Luis Munoz Marin Intl

Sat 5/3

5:30 am-6:22 pm

1 stop12h 52m

$207

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 4/27

12:31 pm-11:48 pm

1 stop11h 17m

San Juan Luis Munoz Marin Intl

Fri 5/2

5:11 pm-12:43 am

1 stop7h 32m

$217

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Thu 7/24

8:29 pm-4:29 pm

1 stop20h 00m

Saint Thomas Island Cyril E King

Mon 7/28

5:14 pm-12:40 pm

1 stop19h 26m

$219

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 5/3

11:06 am-11:57 pm

2 stops12h 51m

San Juan Luis Munoz Marin Intl

Wed 5/7

7:25 am-2:04 pm

1 stop6h 39m

$221

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 5/5

7:18 pm-7:40 pm

2 stops24h 22m

San Juan Luis Munoz Marin Intl

Fri 5/9

8:12 pm-11:46 am

1 stop15h 34m

$257

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sat 6/7

7:10 pm-9:57 am

1 stop14h 47m

Saint Thomas Island Cyril E King

Wed 6/11

10:52 am-11:55 am

1 stop25h 03m

$272

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

Thu 5/29

8:31 pm-5:27 pm

1 stop20h 56m

Santo Domingo Las Americas

Sat 5/31

12:27 pm-12:29 pm

1 stop24h 02m

$294

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Mon 8/25

6:26 am-12:50 pm

1 stop6h 24m

Saint Thomas Island Cyril E King

Fri 8/29

5:25 pm-12:01 am

1 stop6h 36m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 60 results
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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, September is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $254). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $336). 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 April 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cleveland to Caribbean as you normally would.

Rainfall in Caribbean by month

Plan your trip to Caribbean by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean when rainfall is around 2.2 in.

Temperature in Caribbean by month

Plan your trip to Caribbean by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 April 17, 2025.
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very good
9,882 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very good
4,280 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very good
7,917 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Copa Airlines
7.6
Good
1,409 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very good
9,882 reviews

Food

7.1

Overall

8.0

Boarding

8.2

Entertainment

7.1

Comfort

7.9

Crew

8.5

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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.

  • What airport do you fly from for flights from Cleveland to Caribbean?

    Cleveland Hopkins Intl (CLE) is the airport you will fly out of if you book a flight from Cleveland to Caribbean. It is only a 10.1 mi journey to Hopkins Intl (CLE) from Cleveland’s city center.

  • What are the cheapest airlines to fly from Cleveland to Caribbean one-way?

    One-way options have recently been found by users for as low as $97 on Frontier. Other airlines that offer cheap prices include American Airlines from $104 and Delta from $109 one-way.

  • What are the most popular routes from Cleveland to Caribbean?

    While some choose either Cleveland Hopkins Intl - Punta Cana or Cleveland Hopkins Intl - Montego Bay Sangster Intl, Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl is the most popular route from Cleveland to Caribbean.

  • What are the cheapest flights from Cleveland to Caribbean?

    Looking for the cheapest flight from Cleveland to Caribbean? While on average our users pay $174, our data indicates the cheapest price to be $79. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $206.

  • Can I find deals for flights from Cleveland to Caribbean that include hotel bookings?

    Yes. In addition to deals on Cleveland to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Cleveland to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Cleveland to Caribbean.

  • Can I find deals for business class flights from Cleveland to Caribbean?

    Yes. Cheapflights offers flight deals from Cleveland to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Cleveland to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $254). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $336). 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.

See more FAQs

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Alternative routes for Cleveland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$125Average$382FlexibilityNo cancel feeOn-time65%
FrontierCheapest$144Average$380FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$585FlexibilityNo cancel feeOn-time62%
DeltaCheapest$239Average$541FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$259Average$607FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$291Average$618FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$640FlexibilityNo cancel feeOn-time63%

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