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

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 9/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CLE
Aug 3 — Aug 101
Sun 8/3
Sun 8/10
1 adult, Economy
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Cheap flight deals from Caribbean to Cleveland

Keep the following information in mind while searching for Caribbean to Cleveland flight deals. Data was last updated July 29, 2025.

Round-trip from

$194
(American Airlines)

One-way from

$88
(Southwest)

Popular in

November

Cheapest in

February

Average price

$234

Good round-trip deal

$208 or less

Good one-way deal

$148 or less
From Caribbean to Cleveland Hopkins Intl
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One-way flight from Caribbean to Cleveland Hopkins Intl
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Highest demand for flights based on searches. 12% potential increase in price ($39 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Caribbean to Cleveland Hopkins Intl.
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Price to beat on a one-way flight from Caribbean to Cleveland Hopkins Intl.
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Find flight deals from Caribbean to Cleveland

Cheapest flights from Caribbean to Cleveland
Explore the most affordable flight options available from Caribbean to Cleveland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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.
Sat 10/115:00 pmSJU - CLE
1 stop7h 14mAmerican Airlines
Mon 10/208:53 pmCLE - SJU
1 stop17h 15mAmerican Airlines
Deal found 7/27$194
This Delta deal was found by Cheapflights users on 7/28. 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 10/147:00 amSJU - CLE
1 stop10h 10mDelta
Tue 10/217:13 amCLE - SJU
1 stop9h 12mDelta
Deal found 7/28$205
This eDestinos deal was found by Cheapflights users on 7/27. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/21:43 pmSJU - CLE
Nonstop4h 40mFrontier
Tue 8/128:00 amCLE - SJU
Nonstop4h 28mFrontier
Deal found 7/27$216
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1111:59 amSJU - CLE
1 stop6h 57mSpirit Airlines
Thu 9/187:51 pmCLE - SJU
1 stop15h 13mSpirit Airlines
Deal found 7/28$217
This Southwest deal was found by Cheapflights users on 7/29. 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.
Thu 11/66:40 amSJU - CLE
2 stops10h 00mSouthwest
Thu 11/135:45 pmCLE - SJU
1 stop6h 40mSouthwest
Deal found 7/29$247
This United Airlines deal was found by Cheapflights users on 7/29. 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 9/221:05 amSJU - CLE
2 stops15h 46mUnited Airlines
Tue 9/3011:00 amCLE - SJU
2 stops12h 57mUnited Airlines
Deal found 7/29$265
This CheapOair deal was found by Cheapflights users on 7/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/91:43 pmSJU - CLE
Nonstop4h 40mMultiple Airlines
Mon 8/1112:37 pmCLE - SJU
1 stop8h 32mMultiple Airlines
Deal found 7/28$272
This FlightHub deal was found by Cheapflights users on 7/29. 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.
Wed 11/121:12 pmMBJ - CLE
1 stop26h 35mSpirit Airlines
Mon 11/1712:15 pmCLE - MBJ
1 stop23h 50mSpirit Airlines
Deal found 7/29$329
This American Airlines deal was found by Cheapflights users on 7/28. 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 8/211:50 pmPUJ - CLE
1 stop10h 31mAmerican Airlines
Mon 8/256:00 amCLE - PUJ
1 stop8h 45mAmerican Airlines
Deal found 7/28$341
This SmartFares deal was found by Cheapflights users on 7/28. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/285:05 pmSDQ - CLE
1 stop24h 52mSpirit Airlines
Sun 8/317:02 pmCLE - SDQ
1 stop20h 58mSpirit Airlines
Deal found 7/28$343
This United Airlines deal was found by Cheapflights users on 7/28. 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.
Wed 10/84:35 pmPUJ - CLE
1 stop17h 04mUnited Airlines
Sat 10/113:17 pmCLE - PUJ
1 stop24h 24mUnited Airlines
Deal found 7/28$347
This Mytrip deal was found by Cheapflights users on 7/28. 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.
Thu 9/112:12 pmMBJ - CLE
1 stop9h 31mFrontier
Thu 9/187:34 pmCLE - MBJ
1 stop18h 11mFrontier
Deal found 7/28$362

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Cleveland 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 July 29, 2025.
Use the filters below to find and compare flights from Caribbean to Cleveland that are best for you.

Fly from

Caribbean

Fly to

Cleveland

Route

Depart

Return

Price

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Sat 10/11

5:00 pm-12:14 am

1 stop7h 14m

Cleveland Hopkins Intl

Mon 10/20

8:53 pm-2:08 pm

1 stop17h 15m

$194

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Fri 10/3

7:30 am-5:03 pm

1 stop9h 33m

Cleveland Hopkins Intl

Mon 10/6

10:12 am-4:33 pm

1 stop6h 21m

$205

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Sat 8/2

1:43 pm-6:23 pm

Nonstop4h 40m

Cleveland Hopkins Intl

Tue 8/12

8:00 am-12:28 pm

Nonstop4h 28m

$216

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Thu 9/11

11:59 am-6:56 pm

1 stop6h 57m

Cleveland Hopkins Intl

Thu 9/18

7:51 pm-11:04 am

1 stop15h 13m

$217

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Fri 8/22

5:50 am-12:50 pm

1 stop7h 00m

Cleveland Hopkins Intl

Mon 8/25

4:25 pm-11:30 pm

1 stop7h 05m

$247

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Mon 9/22

1:05 am-4:51 pm

2 stops15h 46m

Cleveland Hopkins Intl

Tue 9/30

7:15 am-1:45 pm

1 stop6h 30m

$265

San JuanCleveland

SJU - CLE

SJUCLE

San Juan Luis Munoz Marin Intl

Sat 8/9

1:43 pm-6:23 pm

Nonstop4h 40m

Cleveland Hopkins Intl

Mon 8/11

12:37 pm-9:09 pm

1 stop8h 32m

$272

Montego BayCleveland

MBJ - CLE

MBJCLE

Montego Bay Sangster Intl

Wed 11/12

1:12 pm-3:47 pm

1 stop26h 35m

Cleveland Hopkins Intl

Mon 11/17

12:15 pm-12:05 pm

1 stop23h 50m

$329

Punta CanaCleveland

PUJ - CLE

PUJCLE

Punta Cana

Thu 8/21

1:50 pm-12:21 am

1 stop10h 31m

Cleveland Hopkins Intl

Mon 8/25

6:00 am-2:45 pm

1 stop8h 45m

$341

Santo DomingoCleveland

SDQ - CLE

SDQCLE

Santo Domingo Las Americas

Thu 8/28

5:05 pm-5:57 pm

1 stop24h 52m

Cleveland Hopkins Intl

Sun 8/31

7:02 pm-4:00 pm

1 stop20h 58m

$343

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 60 results
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Best time to book a flight from Caribbean to Cleveland

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

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

Currently, April is the cheapest month in which you can book a flight from Caribbean to Cleveland (average of $250). Flying from Caribbean to Cleveland in June is currently the most expensive (average of $290). 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 CB to CLE?

Find hourly flight availability from Caribbean to Cleveland. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 29, 2025.

When flying from Caribbean to Cleveland, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Weekly flight availability from Caribbean to Cleveland

Explore weekly flight availability from Caribbean to Cleveland. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated July 29, 2025.

The most flights from 0CB to CLE are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

Reviews of airlines servicing Cleveland

Get insights into the airlines that provide service to Cleveland. 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 Cleveland. Reviews last updated July 29, 2025.
Read reviews from past customers who have flown Southwest, Delta, and LATAM Airlines from Caribbean to Cleveland. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,238 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,977 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
LATAM Airlines
7.5
Good
1,821 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Copa Airlines
7.5
Good
1,493 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,899 reviews
Southwest
8.0
Very good
4,238 reviews

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

Entertainment

7.5

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Cleveland. 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 into for flights to Cleveland from Caribbean?

    Most people fly into Cleveland Hopkins Intl (CLE) if they book a flight to Cleveland from Caribbean. Hopkins Intl is conveniently located just 10.1 mi from Cleveland’s city center.

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

    To fly one-way, consider booking your trip with Southwest, which is currently one of the cheapest options available, starting at $88. Delta flights start at $103 while deals on American Airlines start at $105 one-way.

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

    Most travelers choose San Juan Luis Munoz Marin Intl - Cleveland Hopkins Intl, Santo Domingo Las Americas - Cleveland Hopkins Intl or Punta Cana - Cleveland Hopkins Intl when deciding on the best route from Caribbean to Cleveland.

  • What are the cheapest flights from Caribbean to Cleveland?

    The cheapest flight price from Caribbean to Cleveland is $105. On average you can expect to pay $218. The most popular route, (San Juan Luis Munoz Marin Intl - Cleveland Hopkins Intl), can usually be booked for $175.

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

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

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

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

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

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

    Currently, April is the cheapest month in which you can book a flight from Caribbean to Cleveland (average of $250). Flying from Caribbean to Cleveland in June is currently the most expensive (average of $290). 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

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Sandusky
Mentor
Beachwood
Mansfield
Wooster
Independence
Avon
Willoughby
Elyria
Streetsboro
Kent
Cleveland Heights
North Olmsted
Cuyahoga Falls
Macedonia
Strongsville
Medina
Westlake

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Top 5 airlines flying from Caribbean to Cleveland

Discover the top 5 airlines that operate flights from Caribbean to Cleveland. 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 July 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$147Average$260FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$175Average$534FlexibilityNo cancel feeOn-time69%
DeltaCheapest$205Average$456FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$207Average$522FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$250Average$377FlexibilityNo cancel feeOn-time63%

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