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Caribbean Islands

$68+ 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
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap 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 20, 2025.

Round-trip from

$168
(Cheapflightsfares)

One-way from

$68
(eDestinos)

Popular in

December

Cheapest in

April

Average price

$299
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. 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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Find 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 20, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/18. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/97:42 pmCLE - SJU
Nonstop4h 12mFrontier
Sun 4/1312:37 amSJU - CLE
Nonstop4h 58mFrontier
Deal found 2/18$168
This Mytrip deal was found by Cheapflights users on 2/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/268:39 pmCLE - SJU
1 stop19h 55mSpirit Airlines
Wed 4/25:52 amSJU - CLE
2 stops30h 21mSpirit Airlines
Deal found 2/18$169
This FlightHub deal was found by Cheapflights users on 2/18. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/16:00 amCLE - SJU
1 stop10h 34mMultiple Airlines
Fri 4/412:59 amSJU - CLE
Nonstop5h 01mMultiple Airlines
Deal found 2/18$173
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 United Airlines deal was found by Cheapflights users on 2/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/256:00 amCLE - SJU
1 stop9h 36mUnited Airlines
Tue 2/252:05 amSJU - CLE
1 stop7h 54mUnited Airlines
Deal found 2/18$234
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/307:05 amCLE - SJU
1 stop7h 07mDelta
Tue 4/85:16 pmSJU - CLE
1 stop7h 27mDelta
Deal found 2/19$260
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:45 pmCLE - SJU
1 stop16h 30mAmerican Airlines
Tue 3/48:15 amSJU - CLE
1 stop9h 27mAmerican Airlines
Deal found 2/19$264
This CheapOair 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 CheapOair 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 2/20$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 Mytrip 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/256:00 amCLE - MBJ
1 stop6h 02mMultiple Airlines
Fri 4/43:05 pmMBJ - CLE
2 stops22h 25mMultiple Airlines
Deal found 2/20$334
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/155:30 amCLE - PUJ
1 stop30h 14mMultiple Airlines
Sun 5/113:07 pmPUJ - CLE
1 stop24h 40mMultiple Airlines
Deal found 2/19$344
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/258:38 pmCLE - PUJ
2 stops16h 01mFrontier
Fri 4/46:54 pmPUJ - CLE
1 stop11h 06mFrontier
Deal found 2/19$345

Find flights from Cleveland to Caribbean Islands within your budget

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 20, 2025.

Fly from

Cleveland

Fly to

Caribbean Islands

Route

Depart

Return

Price

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 4/9

7:42 pm-11:54 pm

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

Sun 4/13

12:37 am-5:35 am

Nonstop4h 58m

$168

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 3/26

8:39 pm-4:34 pm

1 stop19h 55m

San Juan Luis Munoz Marin Intl

Wed 4/2

5:52 am-12:13 pm

2 stops30h 21m

$169

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 4/1

6:00 am-4:34 pm

1 stop10h 34m

San Juan Luis Munoz Marin Intl

Fri 4/4

12:59 am-6:00 am

Nonstop5h 01m

$173

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 2/25

10:57 am-10:22 pm

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Tue 2/25

2:05 am-8:59 am

1 stop7h 54m

$234

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 3/1

12:15 pm-11:59 pm

1 stop10h 44m

San Juan Luis Munoz Marin Intl

Tue 3/11

7:45 am-6:49 pm

1 stop11h 04m

$239

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 2/28

6:45 pm-12:15 pm

1 stop16h 30m

San Juan Luis Munoz Marin Intl

Tue 3/4

8:15 am-5:06 pm

2 stops9h 51m

$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

Tue 3/25

6:00 am-11:02 am

1 stop6h 02m

Montego Bay Sangster Intl

Fri 4/4

3:05 pm-2:30 pm

2 stops22h 25m

$334

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 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.

Travel insights for flights from Cleveland to Caribbean Islands

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

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

Currently, September is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $254). Flying from Cleveland to Caribbean Islands 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 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 February 20, 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 Islands as you normally would.

Rainfall in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Caribbean Islands 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 Islands when rainfall is around 2.2 in.

Temperature in Caribbean Islands by month

Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Caribbean Islands, 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 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 20, 2025.
Get a feel of what it's like to fly with Southwest, Alaska Airlines and Delta from Cleveland to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
4,411 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
9,692 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
8,220 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
1,510 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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
3,070 reviews
Southwest
8.1
Very good
4,411 reviews

Comfort

8.1

Overall

8.1

Crew

8.7

Food

7.1

Boarding

8.2

Entertainment

7.6

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 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.

  • 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 $68. Users have also found prices from $71 and $120 on Frontier and Delta, respectively.

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

    While some choose either Cleveland Hopkins Intl - Punta Cana or Cleveland Hopkins Intl - Montego Bay Sangster Intl, 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 $225, our data shows the cheapest flight currently is $67. When looking at the most popular route, (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $140 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, September is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $254). Flying from Cleveland to Caribbean Islands 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.

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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 February 20, 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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