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$81+ 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 4/28. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
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 March 28, 2025.

Round-trip from

$178
(CheapOair)

One-way from

$81
(Mytrip)

Popular in

December

Cheapest in

April

Average price

$328

Good round-trip deal

$177 or less

Good one-way deal

$89 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. 19% potential increase in price ($77 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in March 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 March 28, 2025.

This CheapOair deal was found by Cheapflights users on 3/27. 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.
Sun 4/66:27 pmCLE - STT
1 stop17h 53mFrontier
Fri 4/111:10 pmSTT - CLE
1 stop16h 50mFrontier
Deal found 3/27$178
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Sat 4/267:18 pmCLE - SJU
2 stops24h 22mSpirit Airlines
Wed 4/307:00 pmSJU - CLE
2 stops22h 26mSpirit Airlines
Deal found 3/27$184
This Delta deal was found by Cheapflights users on 3/26. 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 4/2612:31 pmCLE - SJU
1 stop11h 17mDelta
Sat 5/36:15 amSJU - CLE
1 stop6h 54mDelta
Deal found 3/26$205
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Thu 4/310:51 amCLE - SJU
1 stop11h 59mAmerican Airlines
Thu 4/105:30 amSJU - CLE
1 stop9h 45mAmerican Airlines
Deal found 3/27$207
This Kiwi.com deal was found by Cheapflights users on 3/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/56:00 amCLE - SJU
1 stop10h 34mMultiple Airlines
Wed 4/2312:05 amSJU - CLE
Nonstop4h 58mMultiple Airlines
Deal found 3/27$223
This Justfly.com deal was found by Cheapflights users on 3/26. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/49:30 pmCLE - STT
1 stop14h 42mMultiple Airlines
Sun 5/114:26 pmSTT - CLE
2 stops25h 49mMultiple Airlines
Deal found 3/26$226
This United Airlines deal was found by Cheapflights users on 3/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/46:05 amCLE - SJU
1 stop9h 35mUnited Airlines
Wed 5/143:56 pmSJU - CLE
1 stop8h 03mUnited Airlines
Deal found 3/27$227
This Cheapflightsfares deal was found by Cheapflights users on 3/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/265:00 pmCLE - SJU
Nonstop4h 12mFrontier
Tue 4/2912:05 amSJU - CLE
Nonstop4h 58mFrontier
Deal found 3/27$234
This Mytrip deal was found by Cheapflights users on 3/27. 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.
Mon 5/57:18 pmCLE - STT
1 stop14h 42mSpirit Airlines
Sat 5/103:49 pmSTT - CLE
1 stop26h 26mSpirit Airlines
Deal found 3/27$236
This Booking.com deal was found by Cheapflights users on 3/26. 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.
Sat 7/268:25 pmCLE - POP
1 stop21h 04mFrontier
Thu 7/316:31 pmPOP - CLE
1 stop15h 08mFrontier
Deal found 3/26$304
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/147:00 amCLE - SJU
1 stop9h 20mJetBlue
Wed 5/216:00 amSJU - CLE
1 stop10h 03mJetBlue
Deal found 3/27$343
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Mon 7/216:03 amCLE - STT
1 stop6h 42mAmerican Airlines
Mon 7/284:00 pmSTT - CLE
1 stop8h 25mAmerican Airlines
Deal found 3/27$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 March 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

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sun 4/6

6:27 pm-12:20 pm

1 stop17h 53m

Saint Thomas Island Cyril E King

Fri 4/11

1:10 pm-6:00 am

1 stop16h 50m

$178

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/26

7:18 pm-7:40 pm

2 stops24h 22m

San Juan Luis Munoz Marin Intl

Wed 4/30

7:00 pm-5:26 pm

2 stops22h 26m

$184

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/26

12:31 pm-11:48 pm

1 stop11h 17m

San Juan Luis Munoz Marin Intl

Sat 5/3

6:15 am-1:09 pm

1 stop6h 54m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/26

6:53 pm-10:50 am

1 stop15h 57m

San Juan Luis Munoz Marin Intl

Sat 5/3

5:30 am-10:47 pm

1 stop17h 17m

$217

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 4/8

6:00 am-4:34 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Tue 4/22

12:05 am-5:03 am

Nonstop4h 58m

$223

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sun 5/4

9:30 pm-12:12 pm

1 stop14h 42m

Saint Thomas Island Cyril E King

Sun 5/11

4:26 pm-6:15 pm

2 stops25h 49m

$226

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 5/4

6:05 am-3:40 pm

1 stop9h 35m

San Juan Luis Munoz Marin Intl

Wed 5/14

3:56 pm-11:59 pm

1 stop8h 03m

$227

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/26

5:00 pm-9:12 pm

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

Tue 4/29

12:05 am-5:03 am

Nonstop4h 58m

$234

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Mon 5/5

7:18 pm-10:00 am

1 stop14h 42m

Saint Thomas Island Cyril E King

Sat 5/10

3:49 pm-6:15 pm

1 stop26h 26m

$236

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 4/8

4:25 pm-10:30 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Tue 4/22

8:00 am-9:15 pm

2 stops13h 15m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

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 March 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 March 28, 2025.
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,274 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,897 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,798 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.5
Good
1,395 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,274 reviews

Comfort

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $81 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $87 and Delta from $103 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 - Oranjestad Reina Beatrix, 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 $187, our data indicates the cheapest price to be $72. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $189.

  • 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 March 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$125Average$357FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$381FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$595FlexibilityNo cancel feeOn-time62%
DeltaCheapest$240Average$534FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$263Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$290Average$592FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$631FlexibilityNo cancel feeOn-time63%
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