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Caribbean

$107+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 septiembre 11, 2025.

Round-trip from

$191
(Kiwi.com)

One-way from

$107
(Mytrip)

Popular in

December

Cheapest in

May

Average price

$269

Good round-trip deal

$323 or less

Good one-way deal

$178 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 ($78 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 September 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 septiembre 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/281:57 pmCLE - SJU
1 stop27h 57mFrontier
jue. 11/69:00 amSJU - CLE
1 stop14h 27mFrontier
Deal found 9/10$191
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/111:56 pmCLE - SJU
1 stop26h 58mFrontier
mar. 11/189:00 amSJU - CLE
1 stop14h 27mFrontier
Deal found 9/10$192
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/281:57 pmCLE - SJU
1 stop27h 57mFrontier
mar. 11/49:00 amSJU - CLE
1 stop14h 27mFrontier
Deal found 9/11$209
This Delta deal was found by Cheapflights users on 9/11. 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. 10/317:13 amCLE - SJU
1 stop9h 12mDelta
jue. 11/67:15 amSJU - CLE
1 stop6h 49mDelta
Deal found 9/11$225
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/281:57 pmCLE - SJU
1 stop27h 57mFrontier
dom. 11/27:30 amSJU - CLE
1 stop18h 27mFrontier
Deal found 9/10$226
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/301:57 pmCLE - SJU
1 stop27h 57mFrontier
jue. 11/69:00 amSJU - CLE
1 stop14h 27mFrontier
Deal found 9/10$228
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/317:51 pmCLE - SJU
2 stops22h 03mMultiple Airlines
mar. 11/49:00 amSJU - CLE
1 stop14h 27mMultiple Airlines
Deal found 9/10$236
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/111:56 pmCLE - SJU
1 stop26h 58mMultiple Airlines
lun. 11/176:00 amSJU - CLE
2 stops31h 17mMultiple Airlines
Deal found 9/10$237
This Kiwi.com deal was found by Cheapflights users on 9/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/82:26 pmCLE - SJU
2 stops24h 33mMultiple Airlines
mié. 10/154:51 pmSJU - CLE
1 stop26h 30mMultiple Airlines
Deal found 9/10$240
This Frontier deal was found by Cheapflights users on 9/11. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 9/292:44 pmCLE - SJU
2 stops19h 12mFrontier
vie. 10/310:57 amSJU - CLE
2 stops13h 46mFrontier
Deal found 9/11$244
This Delta deal was found by Cheapflights users on 9/11. 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. 10/176:00 amCLE - SJU
1 stop10h 33mDelta
mar. 10/281:06 pmSJU - CLE
1 stop9h 58mDelta
Deal found 9/11$245
This Kiwi.com deal was found by Cheapflights users on 9/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/281:57 pmCLE - SJU
1 stop27h 57mFrontier
sáb. 11/15:51 pmSJU - CLE
1 stop29h 30mFrontier
Deal found 9/11$247

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 septiembre 11, 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

vie. 10/31

6:00 am-4:33 pm

1 stop10h 33m

San Juan Luis Munoz Marin Intl

jue. 11/6

7:15 am-1:04 pm

1 stop6h 49m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 10/28

5:15 pm-11:36 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

lun. 11/3

2:05 am-1:14 pm

2 stops12h 09m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mié. 10/29

7:13 am-4:25 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

lun. 11/3

6:43 pm-12:36 am

1 stop6h 53m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mié. 10/15

6:15 am-3:42 pm

1 stop9h 27m

San Juan Luis Munoz Marin Intl

mié. 10/22

3:56 pm-11:58 pm

1 stop8h 02m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

lun. 9/29

7:00 am-4:20 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

vie. 10/3

5:41 pm-12:39 am

1 stop6h 58m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

dom. 10/5

2:13 pm-11:57 pm

1 stop9h 44m

San Juan Luis Munoz Marin Intl

mié. 10/8

1:05 am-10:23 am

1 stop9h 18m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 10/25

12:10 pm-11:56 pm

1 stop11h 46m

San Juan Luis Munoz Marin Intl

sáb. 11/1

7:00 am-5:10 pm

1 stop10h 10m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

lun. 10/20

4:54 pm-11:57 pm

1 stop7h 03m

San Juan Luis Munoz Marin Intl

jue. 10/23

1:05 am-10:23 am

1 stop9h 18m

$225

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 9/20

7:00 am-4:17 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

sáb. 9/27

7:00 am-6:00 pm

1 stop11h 00m

$242

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 10/14

7:15 am-1:45 pm

1 stop6h 30m

San Juan Luis Munoz Marin Intl

lun. 11/10

2:05 am-9:37 am

1 stop8h 32m

$250

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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 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 septiembre 11, 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.

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 septiembre 11, 2025.
See what other customers who have flown with Southwest, Delta, and United Airlines from Cleveland to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,177 reviews
Southwest
8.0
Very good
4,248 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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.

  • How long is the flight from Cleveland to Caribbean?

    Delta, United Airlines, and Spirit Airlines can get you from Cleveland to Caribbean in just under 6h 21m. Your travel time can differ by up to 7h 32m. Airlines will cover a distance of 1841 mi. This flight may include one or multiple stops.

  • 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 $113 on United Airlines. Other airlines that offer cheap prices include Delta from $113 and American Airlines from $139 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 $305, our data indicates the cheapest price to be $152. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $225.

  • 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.

See more FAQs

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Alternative routes for Cleveland to Caribbean

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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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$355FlexibilityNo cancel feeOn-time65%
FrontierCheapest$145Average$401FlexibilityNo cancel feeOn-time62%
DeltaCheapest$173Average$548FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$178Average$605FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$214Average$596FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$245Average$608FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$293Average$637FlexibilityNo cancel feeOn-time63%

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