Caribbean Islands

$88+ 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 7/17. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
jun. 23 — jun. 301
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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 junio 18, 2025.

Round-trip from

$178
(Cheapflightsfares)

One-way from

$88
(Southwest)

Popular in

December

Cheapest in

May

Average price

$266
From Cleveland Hopkins Intl to Caribbean Islands
One-way flight from Cleveland Hopkins Intl to Caribbean Islands
Highest demand for flights based on searches. 20% potential increase in price ($79 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($14 potential savings vs. average RT price).
Average for round-trip flights in June 2025

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 junio 18, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/16. 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.
lun. 8/1111:37 amCLE - SJU
Nonstop4h 30mFrontier
jue. 8/146:00 amSJU - CLE
Nonstop4h 37mFrontier
Deal found 6/16$178
This Priceline deal was found by Cheapflights users on 6/16. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/268:25 pmCLE - STT
1 stop20h 02mFrontier
lun. 6/305:12 pmSTT - CLE
1 stop19h 33mFrontier
Deal found 6/16$192
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 6/292:45 pmCLE - SJU
1 stop8h 30mSouthwest
sáb. 7/55:00 amSJU - CLE
1 stop12h 55mSouthwest
Deal found 6/16$195
This United Airlines deal was found by Cheapflights users on 6/17. 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.
dom. 9/217:00 amCLE - SJU
1 stop6h 45mUnited Airlines
sáb. 9/271:30 pmSJU - CLE
2 stops10h 28mUnited Airlines
Deal found 6/17$205
This FlightHub deal was found by Cheapflights users on 6/16. 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.
mar. 7/112:35 pmCLE - SJU
1 stop14h 00mMultiple Airlines
dom. 7/1310:14 pmSJU - CLE
1 stop13h 18mMultiple Airlines
Deal found 6/16$237
This Priceline deal was found by Cheapflights users on 6/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 7/268:00 amCLE - SXM
1 stop9h 21mFrontier
sáb. 8/26:26 pmSXM - CLE
1 stop16h 11mFrontier
Deal found 6/14$263
This American Airlines deal was found by Cheapflights users on 6/16. 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.
mar. 7/112:10 pmCLE - SJU
2 stops10h 45mAmerican Airlines
vie. 7/117:54 amSJU - CLE
1 stop14h 37mAmerican Airlines
Deal found 6/16$270
This SmartFares deal was found by Cheapflights users on 6/17. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 7/1012:37 pmCLE - SJU
2 stops22h 55mSpirit Airlines
vie. 7/113:50 pmSJU - CLE
2 stops19h 42mSpirit Airlines
Deal found 6/17$281
This Cheapflightsfares deal was found by Cheapflights users on 6/17. 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.
sáb. 8/168:44 pmCLE - STT
1 stop13h 30mSpirit Airlines
sáb. 8/2311:19 amSTT - CLE
1 stop8h 20mSpirit Airlines
Deal found 6/17$290
This FlightHub deal was found by Cheapflights users on 6/17. 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.
lun. 9/87:55 amCLE - STX
1 stop8h 23mSpirit Airlines
lun. 9/155:13 pmSTX - CLE
1 stop7h 06mSpirit Airlines
Deal found 6/17$292
This American Airlines deal was found by Cheapflights users on 6/16. 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.
sáb. 10/186:29 pmCLE - PUJ
1 stop16h 15mAmerican Airlines
jue. 10/235:25 pmPUJ - CLE
1 stop15h 22mAmerican Airlines
Deal found 6/16$319
This Delta deal was found by Cheapflights users on 6/17. 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.
lun. 8/116:00 amCLE - PUJ
1 stop8h 34mDelta
mié. 8/202:40 pmPUJ - CLE
1 stop10h 00mDelta
Deal found 6/17$325

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 junio 18, 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

lun. 8/11

11:37 am-4:07 pm

Nonstop4h 30m

San Juan Luis Munoz Marin Intl

jue. 8/14

6:00 am-10:37 am

Nonstop4h 37m

$178

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

jue. 7/17

11:37 am-4:29 pm

1 stop28h 52m

Saint Thomas Island Cyril E King

lun. 7/21

5:14 pm-6:23 pm

1 stop25h 09m

$192

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

dom. 6/29

2:45 pm-11:15 pm

1 stop8h 30m

San Juan Luis Munoz Marin Intl

sáb. 7/5

5:00 am-5:55 pm

1 stop12h 55m

$195

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 7/1

12:35 pm-2:35 am

1 stop14h 00m

San Juan Luis Munoz Marin Intl

dom. 7/13

10:14 pm-11:32 am

1 stop13h 18m

$237

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

sáb. 7/26

8:00 am-5:21 pm

1 stop9h 21m

Simpson Bay Princess Juliana

sáb. 8/2

6:26 pm-10:37 am

1 stop16h 11m

$263

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 7/1

12:10 pm-10:55 pm

2 stops10h 45m

San Juan Luis Munoz Marin Intl

vie. 7/11

7:54 am-10:31 pm

1 stop14h 37m

$270

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

jue. 7/10

12:37 pm-11:32 am

2 stops22h 55m

San Juan Luis Munoz Marin Intl

vie. 7/11

3:50 pm-11:32 am

2 stops19h 42m

$281

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

sáb. 8/16

8:44 pm-10:14 am

1 stop13h 30m

Saint Thomas Island Cyril E King

sáb. 8/23

11:19 am-7:39 pm

1 stop8h 20m

$290

ClevelandChristiansted

CLE - STX

CLESTX

Cleveland Hopkins Intl

lun. 9/8

7:55 am-4:18 pm

1 stop8h 23m

Christiansted Henry Rohlsen

lun. 9/15

5:13 pm-12:19 am

1 stop7h 06m

$292

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 9/6

7:00 am-1:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

vie. 9/12

1:05 am-1:14 pm

2 stops12h 09m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/17

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, 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 June is currently the most expensive (average of $339). 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 junio 18, 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.

Weekly flight availability from Cleveland to Caribbean Islands

Explore weekly flight availability from Cleveland to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated junio 18, 2025.

The most flights from CLE to zzEPX are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).

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 junio 18, 2025.
Get a feel of what it's like to fly with Southwest, Delta and Copa Airlines 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.

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
8.0
Very good

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

Crew

8.6

Entertainment

7.6

Food

7.1

Overall

8.0

Boarding

8.2

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 Southwest. According to our data, you can fly for as low as $88. Users have also found prices from $94 and $103 on Frontier and Delta, respectively.

  • What are the most popular routes 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 $172, our data shows the cheapest flight currently is $91. When looking at the most popular route, (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $193 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 June is currently the most expensive (average of $339). 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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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 junio 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$144Average$395FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$166Average$377FlexibilityNo cancel feeOn-time65%
DeltaCheapest$203Average$542FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$207Average$573FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$246Average$606FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$290Average$606FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$331Average$637FlexibilityNo cancel feeOn-time63%

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