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$68+ 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 3/31. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Feb 27 — Mar 61
Thu 2/27
Thu 3/6
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 February 22, 2025.

Round-trip from

$172
(Kiwi.com)

One-way from

$68
(eDestinos)

Popular in

December

Cheapest in

April

Average price

$299

Good round-trip deal

$233 or less

Good one-way deal

$109 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. 18% potential increase in price ($72 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 February 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 February 22, 2025.

This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/95:50 pmCLE - SJU
2 stops28h 00mSpirit Airlines
Mon 3/1012:30 amSJU - CLE
2 stops16h 25mSpirit Airlines
Deal found 2/21$173
This FlightHub deal was found by Cheapflights users on 2/21. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/298:55 pmCLE - SJU
1 stop19h 39mMultiple Airlines
Sun 4/612:37 amSJU - CLE
Nonstop4h 58mMultiple Airlines
Deal found 2/21$179
This Cheapflightsfares deal was found by Cheapflights users on 2/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/39:12 pmCLE - SJU
Nonstop4h 20mFrontier
Fri 3/76:05 amSJU - CLE
Nonstop5h 04mFrontier
Deal found 2/21$182
This Mytrip deal was found by Cheapflights users on 2/19. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/89:30 pmCLE - SXM
1 stop19h 16mFrontier
Fri 5/235:00 pmSXM - CLE
1 stop16h 52mFrontier
Deal found 2/19$214
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/312:31 pmCLE - SJU
1 stop11h 17mDelta
Wed 5/72:31 pmSJU - CLE
1 stop10h 05mDelta
Deal found 2/21$239
This American Airlines deal was found by Cheapflights users on 2/21. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/410:40 amCLE - SJU
2 stops9h 20mAmerican Airlines
Wed 3/58:15 amSJU - CLE
1 stop9h 27mAmerican Airlines
Deal found 2/21$259
This FlightHub deal was found by Cheapflights users on 2/22. 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.
Sat 4/58:55 pmCLE - MBJ
1 stop15h 07mSpirit Airlines
Tue 4/812:07 pmMBJ - CLE
1 stop6h 27mSpirit Airlines
Deal found 2/22$283
This FlightHub deal was found by Cheapflights users on 2/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/108:46 pmCLE - SXM
1 stop16h 41mMultiple Airlines
Mon 4/146:26 pmSXM - CLE
1 stop11h 31mMultiple Airlines
Deal found 2/20$306
This United Airlines deal was found by Cheapflights users on 2/21. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/12:00 pmCLE - SJU
1 stop9h 36mUnited Airlines
Mon 3/32:05 amSJU - CLE
1 stop7h 54mUnited Airlines
Deal found 2/21$329
This Kiwi.com deal was found by Cheapflights users on 2/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/15:23 pmCLE - MBJ
1 stop20h 20mMultiple Airlines
Fri 3/71:07 pmMBJ - CLE
1 stop12h 23mMultiple Airlines
Deal found 2/21$331
This Frontier deal was found by Cheapflights users on 2/20. 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.
Mon 5/128:32 pmCLE - PUJ
2 stops21h 06mFrontier
Fri 5/1612:35 pmPUJ - CLE
2 stops19h 05mFrontier
Deal found 2/20$344
This Mytrip deal was found by Cheapflights users on 2/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/279:29 pmCLE - PUJ
1 stop14h 48mSpirit Airlines
Sun 4/63:47 pmPUJ - CLE
2 stops31h 02mSpirit Airlines
Deal found 2/21$345

Find flights from Cleveland to Caribbean within your budget

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 February 22, 2025.

Fly from

Cleveland

Fly to

Caribbean

Route

Depart

Return

Price

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 3/25

6:00 am-4:34 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Wed 3/26

5:05 am-10:10 am

Nonstop5h 05m

$172

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 3/9

5:50 pm-9:50 pm

2 stops28h 00m

San Juan Luis Munoz Marin Intl

Tue 3/11

12:05 pm-4:55 pm

2 stops28h 50m

$173

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 3/29

9:24 pm-1:44 am

Nonstop4h 20m

San Juan Luis Munoz Marin Intl

Tue 4/1

12:59 am-5:57 am

Nonstop4h 58m

$179

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 5/8

9:30 pm-4:46 pm

1 stop19h 16m

Simpson Bay Princess Juliana

Fri 5/23

5:00 pm-9:52 am

1 stop16h 52m

$214

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 3/4

12:15 pm-11:59 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Wed 3/12

6:15 am-4:11 pm

1 stop9h 56m

$239

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 2/28

6:49 pm-11:49 am

1 stop16h 00m

San Juan Luis Munoz Marin Intl

Tue 3/4

2:25 pm-10:45 pm

2 stops9h 20m

$264

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Sat 4/5

8:55 pm-11:02 am

1 stop15h 07m

Montego Bay Sangster Intl

Tue 4/8

12:07 pm-7:34 pm

1 stop6h 27m

$283

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

Thu 4/10

8:46 pm-1:27 pm

1 stop16h 41m

Simpson Bay Princess Juliana

Mon 4/14

6:26 pm-5:57 am

1 stop11h 31m

$306

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Sat 3/1

5:23 pm-1:43 pm

1 stop20h 20m

Montego Bay Sangster Intl

Fri 3/7

1:07 pm-1:30 am

1 stop12h 23m

$331

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

Mon 5/12

8:32 pm-5:38 pm

2 stops21h 06m

Punta Cana

Fri 5/16

12:35 pm-7:40 am

2 stops19h 05m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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.

Travel insights for flights from Cleveland to Caribbean

Get recent, data-driven insights about flights from Cleveland to Caribbean including ideal travel times, pricing trends, and more.

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 March is currently the most expensive (average of $363). 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 February 22, 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.

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 February 22, 2025.
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very good
4,401 reviews
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very good
9,700 reviews
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very good
8,212 reviews
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Copa Airlines
7.6
Good
1,502 reviews
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,069 reviews
Southwest
8.1
Very good
4,401 reviews

Boarding

8.2

Overall

8.1

Crew

8.7

Entertainment

7.6

Comfort

8.1

Food

7.1

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 $68 on Frontier. Other airlines that offer cheap prices include Spirit Airlines from $70 and Delta from $120 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 $225, our data indicates the cheapest price to be $67. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $141.

  • 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 March is currently the most expensive (average of $363). 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 February 22, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$113Average$351FlexibilityNo cancel feeOn-time65%
FrontierCheapest$138Average$392FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$598FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$261Average$607FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$291Average$587FlexibilityNo cancel feeOn-time71%
DeltaCheapest$293Average$529FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$332Average$621FlexibilityNo cancel feeOn-time63%
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