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$93+ 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 7/12. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
jun. 17 — jun. 241
mar. 6/17
mar. 6/24
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 junio 12, 2025.

Round-trip from

$170
(Cheapflightsfares)

One-way from

$93
(Southwest)

Popular in

December

Cheapest in

May

Average price

$266

Good round-trip deal

$187 or less

Good one-way deal

$99 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 ($79 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 June 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 junio 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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.
sáb. 6/281:00 pmCLE - SJU
1 stop6h 19mMultiple Airlines
jue. 7/35:01 amSJU - CLE
Nonstop4h 47mMultiple Airlines
Deal found 6/9$170
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
mar. 7/18:25 pmCLE - SJU
Nonstop4h 19mFrontier
vie. 7/116:00 amSJU - CLE
Nonstop4h 37mFrontier
Deal found 6/11$178
This Priceline deal was found by Cheapflights users on 6/11. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/268:25 pmCLE - STT
1 stop20h 02mFrontier
lun. 6/305:12 pmSTT - CLE
1 stop19h 33mFrontier
Deal found 6/11$192
This Delta deal was found by Cheapflights users on 6/11. 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.
vie. 10/315:30 amCLE - SJU
1 stop7h 40mDelta
jue. 11/66:20 pmSJU - CLE
1 stop7h 16mDelta
Deal found 6/11$205
This Southwest deal was found by Cheapflights users on 6/9. 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.
mié. 6/1810:40 amCLE - SJU
1 stop6h 45mSouthwest
mié. 6/2511:35 amSJU - CLE
1 stop11h 30mSouthwest
Deal found 6/9$255
This United Airlines deal was found by Cheapflights users on 6/10. 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.
mar. 6/172:08 pmCLE - SJU
1 stop9h 46mUnited Airlines
mié. 6/183:56 pmSJU - CLE
1 stop7h 50mUnited Airlines
Deal found 6/10$288
This FlightHub deal was found by Cheapflights users on 6/9. 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.
sáb. 7/123:48 pmCLE - STT
1 stop20h 42mSpirit Airlines
vie. 7/181:25 pmSTT - CLE
1 stop25h 28mSpirit Airlines
Deal found 6/9$300
This FlightHub deal was found by Cheapflights users on 6/12. 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.
lun. 9/87:55 amCLE - STX
1 stop8h 23mSpirit Airlines
lun. 9/155:13 pmSTX - CLE
1 stop7h 06mSpirit Airlines
Deal found 6/12$302
This FlightHub deal was found by Cheapflights users on 6/11. 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.
sáb. 6/2811:24 amCLE - STT
1 stop25h 05mMultiple Airlines
lun. 6/305:12 pmSTT - CLE
1 stop19h 33mMultiple Airlines
Deal found 6/11$306
This Mytrip deal was found by Cheapflights users on 6/10. 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.
sáb. 6/281:00 pmCLE - SJU
1 stop6h 19mSpirit Airlines
mié. 7/22:36 amSJU - CLE
2 stops16h 42mSpirit Airlines
Deal found 6/10$309
This American Airlines deal was found by Cheapflights users on 6/11. 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.
lun. 9/226:00 amCLE - PUJ
1 stop9h 25mAmerican Airlines
vie. 9/264:25 pmPUJ - CLE
1 stop6h 43mAmerican Airlines
Deal found 6/11$319
This Delta deal was found by Cheapflights users on 6/11. 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.
dom. 11/25:30 amCLE - PUJ
1 stop7h 19mDelta
mié. 11/122:03 pmPUJ - CLE
1 stop11h 14mDelta
Deal found 6/11$325

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 junio 12, 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

sáb. 6/28

1:00 pm-7:19 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

jue. 7/3

5:01 am-9:48 am

Nonstop4h 47m

$170

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 7/1

8:25 pm-12:44 am

Nonstop4h 19m

San Juan Luis Munoz Marin Intl

vie. 7/11

6:00 am-10:37 am

Nonstop4h 37m

$178

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

jue. 6/26

8:25 pm-4:27 pm

1 stop20h 02m

Saint Thomas Island Cyril E King

lun. 6/30

5:12 pm-12:45 pm

1 stop19h 33m

$192

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

vie. 10/31

5:30 am-1:10 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

jue. 11/6

6:20 pm-12:36 am

1 stop7h 16m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

jue. 8/7

6:22 pm-5:30 am

1 stop11h 08m

San Juan Luis Munoz Marin Intl

dom. 8/10

2:05 am-11:14 am

1 stop9h 09m

$275

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

sáb. 7/12

3:48 pm-12:30 pm

1 stop20h 42m

Saint Thomas Island Cyril E King

vie. 7/18

1:25 pm-2:53 pm

1 stop25h 28m

$300

ClevelandChristiansted

CLE - STX

CLESTX

Cleveland Hopkins Intl

lun. 9/8

7:55 am-4:18 pm

1 stop8h 23m

Christiansted Henry Rohlsen

lun. 9/15

5:13 pm-12:19 am

1 stop7h 06m

$302

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

sáb. 6/28

11:24 am-12:29 pm

1 stop25h 05m

Saint Thomas Island Cyril E King

lun. 6/30

5:12 pm-12:45 pm

1 stop19h 33m

$306

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 6/28

1:00 pm-7:19 pm

1 stop6h 19m

San Juan Luis Munoz Marin Intl

mié. 7/2

2:36 am-7:18 pm

2 stops16h 42m

$309

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

lun. 8/11

6:00 am-2:15 pm

1 stop8h 15m

Punta Cana

mié. 8/20

4:15 pm-12:21 am

1 stop8h 06m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

Showing 1-10 of 56 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 June is currently the most expensive (average of $339). 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 junio 12, 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.

Weekly flight availability from Cleveland to Caribbean

Explore weekly flight availability from Cleveland to Caribbean. 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 junio 12, 2025.

The most flights from CLE to 0CB 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).

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 junio 12, 2025.
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Alaska Airlines
8.0
Very good
10,000 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Southwest
8.0
Very good
4,287 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Delta
8.0
Very good
7,946 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
Copa Airlines
7.5
Good
1,451 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.
United Airlines
7.4
Good
8,790 reviews
Alaska Airlines
8.0
Very good
10,000 reviews

Overall

8.0

Food

7.1

Boarding

8.1

Comfort

7.8

Entertainment

7.1

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Surinder,May 2025

SEA - YYZ

My wife wanted the aile seat and I always prefer window seat. Luckily we both got the best seats we wanted. The plane was very nice and we enjoyed the best take off and the smooth landing at Toronto. All the services by the staff inside the aeroplane were very nice well appreciated. Thanks again and hope to see you soon.

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 $93 on Southwest. Other airlines that offer cheap prices include Frontier from $94 and American Airlines from $123 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 $167, our data indicates the cheapest price to be $89. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $179.

  • 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 June is currently the most expensive (average of $339). 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.

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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 junio 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$395FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$377FlexibilityNo cancel feeOn-time65%
DeltaCheapest$204Average$541FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$207Average$571FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$246Average$604FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$291Average$612FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$331Average$637FlexibilityNo cancel feeOn-time63%

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