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Caribbean Islands

$88+ Cheap flights from Cleveland (CLE) to Caribbean Islands

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 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Cleveland to Caribbean Islands

Keep the following information in mind while searching for Cleveland to Caribbean Islands flight deals. Data was last updated April 25, 2025.

Round-trip from

$168
(Kiwi.com)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$248
From Cleveland Hopkins Intl to Caribbean Islands
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One-way flight from Cleveland Hopkins Intl to Caribbean Islands
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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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Find flight deals from Cleveland to Caribbean Islands

Cheapest flights from Cleveland to Caribbean Islands
Explore the most affordable flight options available from Cleveland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/205:40 pmCLE - SJU
Nonstop4h 24mFrontier
Thu 5/225:01 amSJU - CLE
Nonstop4h 56mFrontier
Deal found 4/24$168
This United Airlines deal was found by Cheapflights users on 4/25. 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.
Sat 5/34:10 pmCLE - SJU
1 stop7h 44mUnited Airlines
Mon 5/51:05 amSJU - CLE
1 stop9h 53mUnited Airlines
Deal found 4/25$175
This American Airlines deal was found by Cheapflights users on 4/24. 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.
Wed 5/76:00 amCLE - SJU
2 stops9h 00mAmerican Airlines
Tue 5/136:10 amSJU - CLE
2 stops9h 21mAmerican Airlines
Deal found 4/24$179
This FlightHub deal was found by Cheapflights users on 4/24. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/27:18 pmCLE - SJU
1 stop13h 19mMultiple Airlines
Tue 5/612:05 amSJU - CLE
Nonstop4h 56mMultiple Airlines
Deal found 4/24$190
This CheapOair deal was found by Cheapflights users on 4/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/68:29 pmCLE - STT
1 stop20h 00mFrontier
Fri 7/115:14 pmSTT - CLE
1 stop19h 26mFrontier
Deal found 4/24$199
This Delta deal was found by Cheapflights users on 4/24. 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 5/147:12 amCLE - SJU
1 stop9h 32mDelta
Thu 5/297:30 amSJU - CLE
1 stop11h 15mDelta
Deal found 4/24$205
This eDestinos deal was found by Cheapflights users on 4/24. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/27:18 pmCLE - SJU
1 stop13h 19mSpirit Airlines
Mon 5/59:25 amSJU - CLE
1 stop8h 48mSpirit Airlines
Deal found 4/24$258
This JetBlue deal was found by Cheapflights users on 4/23. 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.
Thu 5/297:00 amCLE - SJU
1 stop10h 30mJetBlue
Mon 6/26:00 amSJU - CLE
1 stop10h 03mJetBlue
Deal found 4/23$300
This CheapOair deal was found by Cheapflights users on 4/23. 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 CheapOair 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
Sat 6/1410:47 amSTT - CLE
1 stop25h 08mSpirit Airlines
Deal found 4/23$305
This Cheapflightsfares deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/87:55 amCLE - AUA
1 stop8h 39mSpirit Airlines
Sat 11/156:35 pmAUA - CLE
1 stop6h 44mSpirit Airlines
Deal found 4/23$334
This Trip.com deal was found by Cheapflights users on 4/24. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:18 pmCLE - STT
1 stop17h 39mMultiple Airlines
Sat 5/3110:52 amSTT - CLE
1 stop12h 13mMultiple Airlines
Deal found 4/24$350
This Southwest deal was found by Cheapflights users on 4/24. 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.
Tue 5/204:25 pmCLE - SJU
1 stop6h 05mSouthwest
Sat 5/2410:20 amSJU - CLE
2 stops10h 50mSouthwest
Deal found 4/24$351

Cheapflights Fare Finder

Customize your flight search to find flights from Cleveland to Caribbean Islands 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 25, 2025.
Use the filters below to find and compare flights from Cleveland to Caribbean Islands that are best for you.

Fly from

Cleveland

Fly to

Caribbean Islands

Route

Depart

Return

Price

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 5/20

5:40 pm-10:04 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Thu 5/22

5:01 am-9:57 am

Nonstop4h 56m

$168

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 5/5

7:12 pm-11:10 am

1 stop15h 58m

San Juan Luis Munoz Marin Intl

Thu 5/8

2:30 pm-12:38 am

1 stop10h 08m

$175

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 5/18

7:00 am-1:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Sat 5/24

4:55 pm-11:59 pm

1 stop7h 04m

$186

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sun 7/6

8:29 pm-4:29 pm

1 stop20h 00m

Saint Thomas Island Cyril E King

Fri 7/11

5:14 pm-12:40 pm

1 stop19h 26m

$199

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 5/14

7:12 am-4:44 pm

1 stop9h 32m

San Juan Luis Munoz Marin Intl

Thu 5/29

7:30 am-6:45 pm

1 stop11h 15m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 5/10

5:40 pm-10:04 pm

Nonstop4h 24m

San Juan Luis Munoz Marin Intl

Fri 6/13

2:36 am-9:49 am

1 stop7h 13m

$244

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 6/14

1:00 pm-7:19 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

Fri 6/20

2:36 am-9:49 am

1 stop7h 13m

$294

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 5/29

7:00 am-5:30 pm

1 stop10h 30m

San Juan Luis Munoz Marin Intl

Mon 6/2

6:00 am-4:03 pm

1 stop10h 03m

$300

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

Sat 6/14

10:47 am-11:55 am

1 stop25h 08m

$305

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sat 5/24

4:18 pm-9:57 am

1 stop17h 39m

Saint Thomas Island Cyril E King

Sat 5/31

10:52 am-11:05 pm

1 stop12h 13m

$350

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/24

Showing 1-10 of 55 results
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Best time to book a flight from Cleveland to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands

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

Currently, September is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $254). Flying from Cleveland to Caribbean Islands 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 EPX?

Find hourly flight availability from Cleveland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

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

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

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

If weather is an important factor for your trip to Caribbean Islands, 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 Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated April 25, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Cleveland to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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
9,928 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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
4,287 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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
7,920 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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
1,411 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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
8,685 reviews
Alaska Airlines
8.0
Very good
9,928 reviews

Food

7.1

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.1

Overall

8.0

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 Islands. 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 Islands?

    For a flight from Cleveland to Caribbean Islands, you will be flying from Hopkins Intl. Cleveland Hopkins Intl (CLE) is just 10.1 mi from the center of the city.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $88. Users have also found prices from $97 and $124 on Frontier and Delta, respectively.

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

    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 Islands.

  • What are the cheapest flights from Cleveland to Caribbean Islands?

    While on average a flight from Cleveland to Caribbean Islands is generally $176, our data shows the cheapest flight currently is $97. When looking at the most popular route, (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $170 for that flight.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Cleveland to Caribbean Islands 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 Islands?

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

Discover the top 7 airlines that operate flights from Cleveland to Caribbean Islands. 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 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$125Average$382FlexibilityNo cancel feeOn-time65%
FrontierCheapest$145Average$381FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$193Average$587FlexibilityNo cancel feeOn-time62%
DeltaCheapest$239Average$541FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$608FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$291Average$612FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$331Average$639FlexibilityNo cancel feeOn-time63%

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