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 3/4. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Mar 16 — Mar 231
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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 February 14, 2026.

This Frontier deal was found by Cheapflights users on 2/11. 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.
Mon 3/26:29 pm
CLE
-
SJU
1 stop7h 24m
Frontier
Fri 5/111:07 am
SJU
-
CLE
1 stop9h 48m
Frontier
Deal found 2/11$192
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Sat 2/286:29 pm
CLE
-
SJU
1 stop7h 24m
Frontier
Sat 5/23:19 pm
SJU
-
CLE
1 stop9h 51m
Frontier
Deal found 2/11$194
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Mon 2/232:40 pm
CLE
-
SJU
1 stop22h 42m
Multiple Airlines
Fri 2/274:16 pm
SJU
-
CLE
1 stop7h 55m
Multiple Airlines
Deal found 2/10$196
This Travelocity deal was found by Cheapflights users on 2/10. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/34:47 pm
CLE
-
SJU
1 stop16h 07m
Frontier
Mon 3/95:30 am
SJU
-
CLE
1 stop19h 49m
Frontier
Deal found 2/10$197
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Sun 2/227:18 pm
CLE
-
SJU
1 stop16h 21m
Frontier
Wed 2/254:06 pm
SJU
-
CLE
1 stop16h 28m
Frontier
Deal found 2/11$199
This Kiwi.com deal was found by Cheapflights users on 2/10. 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.
Sat 2/212:40 pm
CLE
-
SJU
1 stop22h 42m
Multiple Airlines
Thu 2/264:22 pm
SJU
-
CLE
1 stop26h 25m
Multiple Airlines
Deal found 2/10$200
This CheapOair deal was found by Cheapflights users on 2/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/244:47 pm
CLE
-
SJU
1 stop16h 07m
Frontier
Tue 3/33:53 am
SJU
-
CLE
1 stop20h 16m
Frontier
Deal found 2/9$201
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
Mon 3/22:40 pm
CLE
-
SJU
2 stops23h 51m
Multiple Airlines
Sat 5/28:00 am
SJU
-
CLE
1 stop7h 20m
Multiple Airlines
Deal found 2/11$202
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/241:55 pm
CLE
-
BQN
1 stop12h 02m
Frontier
Tue 3/33:59 am
BQN
-
CLE
1 stop20h 10m
Frontier
Deal found 2/10$202
This CheapOair deal was found by Cheapflights users on 2/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/99:10 pm
CLE
-
SJU
1 stop12h 44m
Frontier
Mon 5/117:15 am
SJU
-
CLE
1 stop17h 41m
Frontier
Deal found 2/12$203
This Kiwi.com deal was found by Cheapflights users on 2/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:29 pm
CLE
-
SJU
1 stop7h 24m
Frontier
Sat 3/74:41 pm
SJU
-
CLE
1 stop10h 01m
Frontier
Deal found 2/12$204
This Frontier deal was found by Cheapflights users on 2/10. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:33 pm
CLE
-
SJU
1 stop12h 20m
Frontier
Sat 3/79:05 pm
SJU
-
CLE
1 stop10h 55m
Frontier
Deal found 2/10$206

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 February 14, 2026.

Round-trip from

$192
(Frontier)

One-way from

$95
(Super.com)

Popular in

December

Cheapest in

May

Average price

$340
From Cleveland Hopkins Intl to Caribbean Islands
One-way flight from Cleveland Hopkins Intl to Caribbean Islands
Highest demand for flights based on searches. 18% potential increase in price ($74 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 14, 2026.
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

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Wed 5/13

3:20 pm-1:43 am

1 stop10h 23m

Aguadilla Borinquen

Sun 5/17

2:38 am-3:20 pm

1 stop12h 42m

$213

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 3/16

4:31 pm-2:13 am

1 stop9h 42m

San Juan Luis Munoz Marin Intl

Tue 3/24

3:19 pm-1:13 am

1 stop9h 54m

$216

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Tue 2/24

1:55 pm-2:57 am

1 stop12h 02m

Aguadilla Borinquen

Tue 3/3

3:59 am-11:09 pm

1 stop20h 10m

$223

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Sun 3/1

10:45 am-2:57 am

1 stop15h 12m

Aguadilla Borinquen

Sat 3/7

3:27 am-7:46 am

1 stop28h 19m

$234

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Sat 2/28

6:30 am-2:57 am

1 stop19h 27m

Aguadilla Borinquen

Tue 3/3

3:59 am-7:56 am

1 stop28h 57m

$234

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Mon 2/23

1:33 pm-2:57 am

1 stop12h 24m

Aguadilla Borinquen

Wed 2/25

3:58 am-3:34 pm

1 stop12h 36m

$234

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Sat 2/28

2:24 pm-2:57 am

1 stop11h 33m

Aguadilla Borinquen

Fri 3/6

3:47 am-1:13 am

1 stop22h 26m

$234

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Wed 4/22

8:01 pm-12:28 pm

1 stop16h 27m

Saint Thomas Island Cyril E King

Wed 4/29

1:23 pm-7:40 am

1 stop18h 17m

$240

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 2/21

2:57 pm-10:22 pm

1 stop6h 25m

San Juan Luis Munoz Marin Intl

Tue 2/24

7:40 am-5:19 pm

1 stop10h 39m

$256

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 3/4

8:10 am-5:27 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Thu 3/19

6:15 am-3:38 pm

1 stop9h 23m

$256

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/10

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 $199). 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.

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 February 14, 2026.
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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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.

Crew

8.5

Entertainment

7.8

Boarding

8.1

Comfort

7.9

Overall

7.9

Food

7.2

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 25m. Fly via Frontier, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1841 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 $59. Users have also found prices from $88 and $88 on American Airlines and Frontier, respectively.

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

  • 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 $199). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

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 February 14, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$105Average$501FlexibilityNo cancel feeOn-timeN/A
Spirit AirlinesCheapest$119Average$356FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$154Average$563FlexibilityNo cancel feeOn-time62%
FrontierCheapest$156Average$418FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$216Average$571FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$566FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$651FlexibilityNo cancel feeOn-time63%

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