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Caribbean Islands

$95+ Cheap flights from Cleveland (CLE) to Caribbean Islands

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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jan 20 — Jan 271
Tue 1/20
Tue 1/27
1 adult, Economy
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Cheap flight deals from Cleveland to Caribbean Islands

Cheapest flights from Cleveland to Caribbean Islands
Explore the most affordable flight options available from Cleveland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 21, 2025.

This CheapOair deal was found by Cheapflights users on 12/21. 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 12/287:59 pmCLE - SJU
Nonstop4h 25mFrontier
Sat 1/104:07 pmSJU - CLE
1 stop16h 46mFrontier
Deal found 12/21$226
This eDestinos deal was found by Cheapflights users on 12/21. 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.
Tue 12/308:14 pmCLE - SJU
Nonstop4h 25mFrontier
Mon 1/125:45 amSJU - CLE
1 stop18h 37mFrontier
Deal found 12/21$235
This Frontier deal was found by Cheapflights users on 12/21. 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.
Sun 12/287:59 pmCLE - SJU
Nonstop4h 25mFrontier
Wed 12/317:30 amSJU - CLE
1 stop10h 00mFrontier
Deal found 12/21$237
This Frontier deal was found by Cheapflights users on 12/20. 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.
Wed 12/316:20 amCLE - SJU
1 stop7h 36mFrontier
Wed 12/319:37 pmSJU - CLE
1 stop11h 06mFrontier
Deal found 12/20$240
This eDestinos deal was found by Cheapflights users on 12/18. 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.
Mon 12/2210:00 pmCLE - SJU
1 stop9h 58mFrontier
Mon 1/129:23 pmSJU - CLE
1 stop20h 44mFrontier
Deal found 12/18$246
This eDestinos deal was found by Cheapflights users on 12/19. 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.
Mon 12/225:40 amCLE - SJU
1 stop18h 14mFrontier
Wed 1/73:08 pmSJU - CLE
1 stop21h 46mFrontier
Deal found 12/19$247
This Frontier deal was found by Cheapflights users on 12/20. 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.
Sat 12/278:05 pmCLE - SJU
Nonstop4h 25mFrontier
Wed 12/317:30 amSJU - CLE
1 stop10h 00mFrontier
Deal found 12/20$251
This eDestinos deal was found by Cheapflights users on 12/18. 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 12/278:05 pmCLE - SJU
Nonstop4h 25mFrontier
Wed 12/313:54 amSJU - CLE
1 stop21h 42mFrontier
Deal found 12/18$252
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Sun 12/287:59 pmCLE - SJU
Nonstop4h 25mFrontier
Wed 1/73:08 pmSJU - CLE
1 stop21h 46mFrontier
Deal found 12/20$253
This eDestinos deal was found by Cheapflights users on 12/19. 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.
Tue 12/308:14 pmCLE - SJU
Nonstop4h 25mFrontier
Wed 1/73:08 pmSJU - CLE
1 stop29h 00mFrontier
Deal found 12/19$254
This eDestinos deal was found by Cheapflights users on 12/19. 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.
Wed 12/319:30 pmCLE - SJU
1 stop17h 01mFrontier
Wed 1/77:05 pmSJU - CLE
2 stops29h 08mFrontier
Deal found 12/19$255
This Kiwi.com deal was found by Cheapflights users on 12/20. 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.
Thu 12/258:20 pmCLE - AUA
2 stops38h 00mMultiple Airlines
Tue 12/304:40 pmAUA - CLE
1 stop8h 19mMultiple Airlines
Deal found 12/20$396

Find flight deals from Cleveland to Caribbean Islands

Keep the following information in mind while searching for Cleveland to Caribbean Islands flight deals. Data was last updated December 21, 2025.

Round-trip from

$226
(Expedia)

One-way from

$95
(Frontier)

Popular in

December

Cheapest in

May

Average price

$489
From Cleveland Hopkins Intl to Caribbean Islands
Search Deals
One-way flight from Cleveland Hopkins Intl to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($81 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Cleveland to Caribbean Islands 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 December 21, 2025.
Use the filters below to find and compare flights from Cleveland to Caribbean Islands that are best for you.

Fly from

Cleveland

Fly to

Caribbean Islands

Route

Depart

Return

Price

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 4/19

6:00 am-1:14 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Sat 4/25

1:50 pm-8:57 pm

1 stop7h 07m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/18

1:48 pm-8:06 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Fri 4/24

1:50 pm-8:57 pm

1 stop7h 07m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 4/19

7:00 am-1:14 pm

1 stop6h 14m

San Juan Luis Munoz Marin Intl

Fri 4/24

1:50 pm-8:57 pm

1 stop7h 07m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/18

1:48 pm-8:06 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Wed 4/22

6:15 am-12:43 pm

1 stop6h 28m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 4/19

6:00 am-1:14 pm

1 stop7h 14m

San Juan Luis Munoz Marin Intl

Thu 4/23

6:15 am-12:43 pm

1 stop6h 28m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/18

1:48 pm-8:06 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Sat 4/25

1:50 pm-8:57 pm

1 stop7h 07m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 2/15

5:55 pm-6:11 am

2 stops11h 16m

San Juan Luis Munoz Marin Intl

Thu 2/19

8:10 am-2:16 pm

1 stop7h 06m

$267

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Sun 2/8

7:21 pm-3:35 pm

1 stop19h 14m

Oranjestad Reina Beatrix

Thu 2/12

4:40 pm-12:29 am

1 stop8h 49m

$268

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 4/16

1:48 pm-8:06 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Wed 4/22

6:15 am-12:43 pm

1 stop6h 28m

$268

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 4/16

1:48 pm-8:06 pm

1 stop6h 18m

San Juan Luis Munoz Marin Intl

Sat 4/25

1:50 pm-8:57 pm

1 stop7h 07m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/19

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

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

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

Currently, November is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $103). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $202). 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 EPX?

Find hourly flight availability from Cleveland to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 21, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Cleveland to Caribbean Islands by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Cleveland to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Cleveland to Caribbean Islands flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday mornings flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated December 21, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Cleveland to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,014 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,102 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,052 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,193 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,077 reviews
Delta
7.9
Good
8,014 reviews

Comfort

7.9

Crew

8.5

Food

7.3

Boarding

8.1

Overall

7.9

Entertainment

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

    For a flight from Cleveland to Caribbean Islands, you will be flying from Hopkins Intl. Cleveland Hopkins Intl (CLE) is just 10.1 mi from the center of the city.

  • How long is the flight from Cleveland to Caribbean Islands?

    There are many flights that can get you from Cleveland to Caribbean Islands in 6h 46m. Fly via Delta, Spirit Airlines, or Frontier to get the fastest option. Airlines will cover a distance of 1599 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $57. Users have also found prices from $72 and $88 on Frontier and American Airlines, respectively.

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

    While some choose either Cleveland Hopkins Intl - Oranjestad Reina Beatrix or Cleveland Hopkins Intl - Punta Cana, Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl is the most popular route from Cleveland to Caribbean Islands.

  • What are the cheapest flights from Cleveland to Caribbean Islands?

    While on average a flight from Cleveland to Caribbean Islands is generally $323, our data shows the cheapest flight currently is $124. When looking at the most popular route, (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $178 for that flight.

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

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $103). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $202). 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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Top 7 airlines flying from Cleveland to Caribbean Islands

Discover the top 7 airlines that operate flights from Cleveland to Caribbean Islands. 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 December 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$346FlexibilityNo cancel feeOn-time65%
FrontierCheapest$153Average$409FlexibilityNo cancel feeOn-time62%
DeltaCheapest$163Average$542FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$211Average$586FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$585FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$264Average$624FlexibilityNo cancel feeOn-time63%
JetBlueCheapest$278Average$577FlexibilityNo cancel feeOn-time62%

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