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$88+ 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
May 3 — May 101
Sat 5/3
Sat 5/10
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 28, 2025.

Round-trip from

$175
(American Airlines)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$248

Good round-trip deal

$198 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 28, 2025.

This United Airlines deal was found by Cheapflights users on 4/28. 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 5/54:10 pmCLE - SJU
1 stop7h 44mUnited Airlines
Tue 5/67:45 amSJU - CLE
1 stop9h 06mUnited Airlines
Deal found 4/28$170
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/48:15 amCLE - SJU
1 stop12h 13mAmerican Airlines
Thu 5/81:30 pmSJU - CLE
2 stops10h 28mAmerican Airlines
Deal found 4/27$175
This Cheapflightsfares deal was found by Cheapflights users on 4/28. 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.
Tue 5/205:40 pmCLE - SJU
Nonstop4h 24mFrontier
Wed 5/288:00 amSJU - CLE
Nonstop4h 51mFrontier
Deal found 4/28$194
This Delta deal was found by Cheapflights users on 4/28. 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 5/67:10 amCLE - SJU
1 stop9h 17mDelta
Wed 6/41:12 pmSJU - CLE
1 stop10h 23mDelta
Deal found 4/28$205
This CheapOair deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/38:25 pmCLE - STT
1 stop20h 02mFrontier
Mon 7/75:14 pmSTT - CLE
1 stop19h 26mFrontier
Deal found 4/27$219
This FlightHub deal was found by Cheapflights users on 4/28. 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.
Mon 5/199:30 pmCLE - SJU
Nonstop4h 21mMultiple Airlines
Sat 5/248:12 pmSJU - CLE
1 stop22h 03mMultiple Airlines
Deal found 4/28$229
This Southwest deal was found by Cheapflights users on 4/28. 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 5/175:15 pmCLE - SJU
1 stop6h 20mSouthwest
Sat 5/245:25 amSJU - CLE
1 stop6h 40mSouthwest
Deal found 4/28$246
This JetBlue deal was found by Cheapflights users on 4/28. 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 4/28$300
This Mytrip deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/115:41 pmCLE - STT
1 stop16h 07mSpirit Airlines
Wed 6/1810:47 amSTT - CLE
1 stop25h 08mSpirit Airlines
Deal found 4/27$301
This Mytrip deal was found by Cheapflights users on 4/28. 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 5/127:10 pmCLE - SJU
2 stops29h 44mSpirit Airlines
Fri 5/168:12 pmSJU - CLE
1 stop15h 34mSpirit Airlines
Deal found 4/28$327
This Trip.com deal was found by Cheapflights users on 4/28. 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 5/288:31 pmCLE - STT
1 stop12h 04mMultiple Airlines
Wed 6/49:10 amSTT - CLE
1 stop25h 33mMultiple Airlines
Deal found 4/28$328
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/258:12 pmCLE - STT
2 stops19h 48mAmerican Airlines
Thu 10/21:50 pmSTT - CLE
1 stop9h 59mAmerican Airlines
Deal found 4/28$351

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 28, 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

Mon 5/5

7:00 am-1:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Mon 5/5

1:05 am-1:13 pm

2 stops12h 08m

$170

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 5/7

7:12 pm-11:10 am

1 stop15h 58m

San Juan Luis Munoz Marin Intl

Wed 5/14

3:35 pm-11:57 pm

1 stop8h 22m

$175

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

Wed 5/28

8:00 am-12:51 pm

Nonstop4h 51m

$194

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 5/6

7:10 am-4:27 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Wed 6/4

1:12 pm-11:35 pm

1 stop10h 23m

$205

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Thu 7/3

8:25 pm-4:27 pm

1 stop20h 02m

Saint Thomas Island Cyril E King

Mon 7/7

5:14 pm-12:40 pm

1 stop19h 26m

$219

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 6/20

1:00 pm-7:19 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

Fri 6/27

5:01 am-9:48 am

Nonstop4h 47m

$266

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 5/26

7:10 pm-3:00 pm

1 stop19h 50m

San Juan Luis Munoz Marin Intl

Thu 5/29

8:12 pm-6:15 pm

1 stop22h 03m

$271

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

Thu 6/12

6:00 am-2:09 pm

1 stop8h 09m

$300

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Wed 6/11

5:41 pm-9:48 am

1 stop16h 07m

Saint Thomas Island Cyril E King

Wed 6/18

10:47 am-11:55 am

1 stop25h 08m

$301

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Wed 5/28

8:31 pm-8:35 am

1 stop12h 04m

Saint Thomas Island Cyril E King

Wed 6/4

9:10 am-10:43 am

1 stop25h 33m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

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 28, 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 28, 2025.
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Delta
8.0
Very good
7,929 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Alaska Airlines
8.0
Very good
9,949 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Southwest
8.0
Very good
4,292 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
Copa Airlines
7.5
Good
1,410 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.
United Airlines
7.4
Good
8,696 reviews
Delta
8.0
Very good
7,929 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Aaron,Oct 2024

LAX - LHR

This was a flight operated by Virgin Atlantic in their Upper Class cabin. Overall, an outstanding experience.

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 $88 on American Airlines. Other airlines that offer cheap prices include Frontier from $88 and Delta from $104 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 $167, our data indicates the cheapest price to be $95. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $197.

  • 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$125Average$383FlexibilityNo cancel feeOn-time65%
FrontierCheapest$145Average$387FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$193Average$568FlexibilityNo cancel feeOn-time62%
DeltaCheapest$239Average$543FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$261Average$608FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$287Average$609FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$331Average$638FlexibilityNo cancel feeOn-time63%

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