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$95+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
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Cheap 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 December 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 12/11. 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.
Mon 12/1510:54 amCLE - SJU
1 stop12h 51mSpirit Airlines
Tue 12/234:10 amSJU - CLE
1 stop7h 27mSpirit Airlines
Deal found 12/11$235
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1510:54 amCLE - SJU
1 stop12h 51mMultiple Airlines
Fri 1/96:18 pmSJU - CLE
1 stop7h 08mMultiple Airlines
Deal found 12/10$239
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/137:17 pmCLE - SJU
1 stop6h 33mFrontier
Thu 12/185:09 pmSJU - CLE
1 stop7h 42mFrontier
Deal found 12/10$240
This Frontier deal was found by Cheapflights users on 12/10. 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 12/152:55 pmCLE - SJU
1 stop8h 01mFrontier
Thu 12/189:37 pmSJU - CLE
1 stop13h 44mFrontier
Deal found 12/10$243
This CheapOair deal was found by Cheapflights users on 12/10. 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.
Sat 12/139:30 pmCLE - SJU
1 stop15h 59mFrontier
Fri 12/193:54 amSJU - CLE
1 stop16h 55mFrontier
Deal found 12/10$244
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/139:30 pmCLE - SJU
1 stop15h 59mFrontier
Tue 12/239:37 pmSJU - CLE
1 stop11h 06mFrontier
Deal found 12/10$245
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sun 12/215:22 pmCLE - SJU
1 stop14h 17mMultiple Airlines
Fri 1/95:18 pmSJU - CLE
2 stops30h 55mMultiple Airlines
Deal found 12/10$247
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sun 12/215:22 pmCLE - SJU
1 stop14h 17mFrontier
Mon 12/293:54 amSJU - CLE
1 stop22h 00mFrontier
Deal found 12/10$254
This Kiwi.com deal was found by Cheapflights users on 12/11. 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 12/147:17 pmCLE - SJU
1 stop6h 33mFrontier
Thu 12/1810:08 amSJU - CLE
1 stop7h 46mFrontier
Deal found 12/11$256
This Frontier deal was found by Cheapflights users on 12/11. 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.
Sun 12/146:00 amCLE - SJU
1 stop13h 08mFrontier
Mon 12/224:21 pmSJU - CLE
1 stop8h 06mFrontier
Deal found 12/11$259
This CheapOair deal was found by Cheapflights users on 12/9. 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.
Fri 12/121:58 pmCLE - SJU
1 stop8h 16mFrontier
Tue 12/163:55 amSJU - CLE
1 stop19h 51mFrontier
Deal found 12/9$260
This Frontier deal was found by Cheapflights users on 12/11. 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.
Sat 12/206:20 amCLE - NAS
1 stop9h 47mFrontier
Sat 12/275:22 pmNAS - CLE
1 stop5h 56mFrontier
Deal found 12/11$331

Find flight deals from Cleveland to Caribbean

Keep the following information in mind while searching for Cleveland to Caribbean flight deals. Data was last updated December 12, 2025.

Round-trip from

$230
(Kiwi.com)

One-way from

$95
(Frontier)

Popular in

December

Cheapest in

May

Average price

$500

Good round-trip deal

$326 or less

Good one-way deal

$124 or less
From Cleveland Hopkins Intl to Caribbean
Search Deals
One-way flight from Cleveland Hopkins Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 21% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($17 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals
Price to beat on a round-trip flight from Cleveland Hopkins Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Cleveland Hopkins Intl to Caribbean.
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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 December 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

Fri 1/9

7:24 pm-3:33 pm

2 stops43h 09m

San Juan Luis Munoz Marin Intl

Sat 1/17

8:00 am-9:32 pm

1 stop14h 32m

$230

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 1/24

1:10 pm-11:56 pm

2 stops9h 46m

San Juan Luis Munoz Marin Intl

Sat 1/31

1:24 pm-11:54 pm

2 stops11h 30m

$271

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 1/4

5:22 pm-8:39 am

1 stop14h 17m

San Juan Luis Munoz Marin Intl

Wed 1/7

8:08 pm-11:54 am

2 stops16h 46m

$296

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Sun 1/25

7:01 pm-2:10 pm

1 stop18h 09m

Simpson Bay Princess Juliana

Sun 2/1

3:15 pm-11:11 pm

2 stops32h 56m

$298

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 12/24

6:59 pm-3:59 pm

1 stop20h 00m

San Juan Luis Munoz Marin Intl

Fri 12/26

3:54 am-7:49 pm

1 stop16h 55m

$309

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 12/21

5:22 pm-8:39 am

1 stop14h 17m

San Juan Luis Munoz Marin Intl

Mon 12/29

6:15 am-8:03 pm

1 stop14h 48m

$310

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

Sat 1/24

6:00 pm-9:59 am

1 stop14h 59m

Santo Domingo Las Americas

Thu 1/29

3:32 pm-10:44 pm

1 stop8h 12m

$311

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 1/22

3:44 pm-2:10 pm

1 stop21h 26m

Simpson Bay Princess Juliana

Thu 1/29

3:15 pm-1:48 pm

2 stops23h 33m

$311

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Sat 1/24

6:44 am-3:38 pm

1 stop8h 54m

Providenciales

Sat 1/31

4:50 pm-7:34 am

1 stop14h 44m

$314

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

Sat 1/24

6:00 pm-9:59 am

1 stop14h 59m

Santo Domingo Las Americas

Fri 1/30

3:32 pm-10:44 pm

1 stop8h 12m

$314

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $103). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $211). 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 December 12, 2025.

It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 21% on the flight price compared to flying in the morning, which is usually more expensive.

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

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

Travelers seeking maximum savings on their Cleveland to Caribbean 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

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 December 12, 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
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.8
Fair
3,084 reviews
Southwest
7.9
Good
4,253 reviews

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

7.9

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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?

    American Airlines, Frontier, and Delta can get you from Cleveland to Caribbean in just under 8h 20m. Your travel time can differ by up to 11h 40m. Airlines will cover a distance of 2120 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 $57 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $80 and American Airlines from $88 one-way.

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

    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.

  • What are the cheapest flights from Cleveland to Caribbean?

    Looking for the cheapest flight from Cleveland to Caribbean? While on average our users pay $319, our data indicates the cheapest price to be $56. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $169.

  • 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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $103). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $211). 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

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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$346FlexibilityNo cancel feeOn-time65%
FrontierCheapest$154Average$399FlexibilityNo cancel feeOn-time62%
DeltaCheapest$166Average$542FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$203Average$547FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$209Average$592FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$589FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$266Average$625FlexibilityNo cancel feeOn-time63%

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