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$88+ 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 3/26. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
mar. 26 — abr. 21
mié. 3/26
mié. 4/2
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 marzo 21, 2025.

Round-trip from

$175
(United Airlines)

One-way from

$88
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$331

Good round-trip deal

$186 or less

Good one-way deal

$89 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. 19% potential increase in price ($78 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 March 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 marzo 21, 2025.

This United Airlines deal was found by Cheapflights users on 3/20. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/43:46 pmCLE - SJU
1 stop8h 11mUnited Airlines
vie. 5/97:25 amSJU - CLE
1 stop6h 39mUnited Airlines
Deal found 3/20$175
This Mytrip deal was found by Cheapflights users on 3/19. 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.
sáb. 5/107:10 pmCLE - SJU
2 stops16h 19mSpirit Airlines
vie. 5/1612:34 pmSJU - CLE
2 stops23h 12mSpirit Airlines
Deal found 3/19$179
This American Airlines deal was found by Cheapflights users on 3/20. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/67:12 pmCLE - SJU
1 stop15h 58mAmerican Airlines
mié. 6/45:25 amSJU - CLE
1 stop17h 35mAmerican Airlines
Deal found 3/20$201
This Delta deal was found by Cheapflights users on 3/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/312:31 pmCLE - SJU
1 stop11h 17mDelta
mié. 5/77:00 amSJU - CLE
1 stop11h 51mDelta
Deal found 3/20$205
This Cheapflightsfares deal was found by Cheapflights users on 3/20. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/107:10 pmCLE - STT
1 stop14h 47mSpirit Airlines
vie. 5/1610:52 amSTT - CLE
1 stop7h 23mSpirit Airlines
Deal found 3/20$208
This CheapOair deal was found by Cheapflights users on 3/20. 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.
sáb. 4/59:57 pmCLE - SJU
Nonstop4h 12mMultiple Airlines
sáb. 5/39:32 amSJU - CLE
1 stop8h 41mMultiple Airlines
Deal found 3/20$223
This Frontier deal was found by Cheapflights users on 3/20. 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.
mar. 4/229:30 pmCLE - SJU
Nonstop4h 12mFrontier
lun. 4/2812:05 amSJU - CLE
Nonstop4h 58mFrontier
Deal found 3/20$228
This CheapOair deal was found by Cheapflights users on 3/20. 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.
jue. 4/106:27 pmCLE - STT
1 stop17h 53mFrontier
lun. 4/141:10 pmSTT - CLE
1 stop16h 47mFrontier
Deal found 3/20$313
This Mytrip deal was found by Cheapflights users on 3/20. 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.
mar. 4/18:39 pmCLE - SXM
1 stop17h 21mSpirit Airlines
mié. 4/303:05 pmSXM - CLE
1 stop26h 21mSpirit Airlines
Deal found 3/20$328
This Delta deal was found by Cheapflights users on 3/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 9/136:00 amCLE - STT
1 stop8h 40mDelta
sáb. 9/203:50 pmSTT - CLE
1 stop8h 48mDelta
Deal found 3/20$351
This CheapOair deal was found by Cheapflights users on 3/21. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/16:00 amCLE - PUJ
1 stop8h 42mSpirit Airlines
jue. 4/173:48 pmPUJ - CLE
1 stop26h 25mSpirit Airlines
Deal found 3/21$377
This Priceline deal was found by Cheapflights users on 3/20. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/16:00 amCLE - PUJ
1 stop8h 42mMultiple Airlines
mar. 4/151:04 pmPUJ - CLE
Nonstop4h 43mMultiple Airlines
Deal found 3/20$382

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 marzo 21, 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

dom. 5/4

3:46 pm-11:57 pm

1 stop8h 11m

San Juan Luis Munoz Marin Intl

vie. 5/9

7:25 am-2:04 pm

1 stop6h 39m

$175

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 5/10

7:10 pm-11:29 am

2 stops16h 19m

San Juan Luis Munoz Marin Intl

vie. 5/16

12:34 pm-11:46 am

2 stops23h 12m

$179

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 5/6

7:12 pm-11:10 am

1 stop15h 58m

San Juan Luis Munoz Marin Intl

mié. 6/4

5:25 am-11:00 pm

1 stop17h 35m

$201

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 5/3

12:31 pm-11:48 pm

1 stop11h 17m

San Juan Luis Munoz Marin Intl

mié. 5/7

7:00 am-6:51 pm

1 stop11h 51m

$205

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

sáb. 5/10

7:10 pm-9:57 am

1 stop14h 47m

Saint Thomas Island Cyril E King

vie. 5/16

10:52 am-6:15 pm

1 stop7h 23m

$208

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 4/5

9:57 pm-2:09 am

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

sáb. 5/3

9:32 am-6:13 pm

1 stop8h 41m

$223

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 4/22

9:30 pm-1:42 am

Nonstop4h 12m

San Juan Luis Munoz Marin Intl

lun. 4/28

12:05 am-5:03 am

Nonstop4h 58m

$228

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

jue. 4/10

6:27 pm-12:20 pm

1 stop17h 53m

Saint Thomas Island Cyril E King

lun. 4/14

1:10 pm-5:57 am

1 stop16h 47m

$313

ClevelandSimpson Bay

CLE - SXM

CLESXM

Cleveland Hopkins Intl

mar. 4/1

8:39 pm-2:00 pm

1 stop17h 21m

Simpson Bay Princess Juliana

mié. 4/30

3:05 pm-5:26 pm

1 stop26h 21m

$328

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

sáb. 9/13

6:00 am-2:40 pm

1 stop8h 40m

Saint Thomas Island Cyril E King

sáb. 9/20

3:50 pm-12:38 am

1 stop8h 48m

$351

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 52 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, 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 $337). 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 marzo 21, 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 marzo 21, 2025.
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,278 reviews
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very good
9,759 reviews
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,895 reviews
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Copa Airlines
7.6
Good
1,400 reviews
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,605 reviews
Southwest
8.1
Very good
4,278 reviews

Boarding

8.2

Food

7.1

Comfort

8.1

Entertainment

7.6

Crew

8.7

Overall

8.1

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 $88 on American Airlines. Other airlines that offer cheap prices include Spirit Airlines from $89 and Delta from $103 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 - Montego Bay Sangster Intl, 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 $189, our data indicates the cheapest price to be $77. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $179.

  • 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 $337). 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 marzo 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$125Average$355FlexibilityNo cancel feeOn-time65%
FrontierCheapest$137Average$386FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$207Average$598FlexibilityNo cancel feeOn-time62%
DeltaCheapest$240Average$532FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$265Average$609FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$291Average$589FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$332Average$631FlexibilityNo cancel feeOn-time63%
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