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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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
ago. 2 — ago. 91
sáb. 8/2
sáb. 8/9
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 julio 28, 2025.

Round-trip from

$187
(United Airlines)

One-way from

$88
(Southwest)

Popular in

December

Cheapest in

May

Average price

$277

Good round-trip deal

$237 or less

Good one-way deal

$125 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 ($13 potential savings vs. average RT price).
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Average for round-trip flights in July 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 julio 28, 2025.

This American Airlines deal was found by Cheapflights users on 7/27. 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.
mié. 9/244:34 pmCLE - SJU
2 stops18h 37mAmerican Airlines
sáb. 9/273:55 pmSJU - CLE
1 stop6h 55mAmerican Airlines
Deal found 7/27$190
This Delta deal was found by Cheapflights users on 7/26. 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. 8/3012:30 pmCLE - SJU
1 stop9h 37mDelta
sáb. 9/207:30 amSJU - CLE
1 stop7h 55mDelta
Deal found 7/26$205
This eDestinos deal was found by Cheapflights users on 7/26. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/1011:37 amCLE - SJU
Nonstop4h 30mFrontier
jue. 8/146:00 amSJU - CLE
Nonstop4h 37mFrontier
Deal found 7/26$214
This United Airlines deal was found by Cheapflights users on 7/28. 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.
mié. 10/1511:00 amCLE - SJU
2 stops12h 57mUnited Airlines
mié. 10/221:30 pmSJU - CLE
1 stop7h 29mUnited Airlines
Deal found 7/28$228
This FlightHub deal was found by Cheapflights users on 7/26. 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.
sáb. 9/204:45 pmCLE - SJU
1 stop18h 19mSpirit Airlines
vie. 9/261:59 amSJU - CLE
2 stops13h 51mSpirit Airlines
Deal found 7/26$233
This Southwest deal was found by Cheapflights users on 7/27. 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.
lun. 9/14:25 pmCLE - SJU
1 stop7h 05mSouthwest
vie. 9/265:50 amSJU - CLE
1 stop11h 00mSouthwest
Deal found 7/27$247
This FlightHub deal was found by Cheapflights users on 7/26. 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.
jue. 9/257:51 pmCLE - STT
1 stop13h 53mSpirit Airlines
jue. 10/210:49 amSTT - CLE
1 stop8h 07mSpirit Airlines
Deal found 7/26$269
This Mytrip deal was found by Cheapflights users on 7/27. 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.
lun. 8/1110:00 pmCLE - PUJ
2 stops38h 09mFrontier
jue. 8/1411:25 amPUJ - CLE
1 stop7h 05mFrontier
Deal found 7/27$308
This FlightHub deal was found by Cheapflights users on 7/27. 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.
sáb. 8/237:02 pmCLE - STX
1 stop16h 24mSpirit Airlines
sáb. 8/3012:57 pmSTX - CLE
1 stop29h 00mSpirit Airlines
Deal found 7/27$313
This American Airlines deal was found by Cheapflights users on 7/26. 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.
lun. 10/206:00 amCLE - PUJ
1 stop6h 27mAmerican Airlines
mié. 10/221:48 pmPUJ - CLE
1 stop10h 27mAmerican Airlines
Deal found 7/26$323
This Kiwi.com deal was found by Cheapflights users on 7/27. 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.
lun. 8/1110:00 pmCLE - PUJ
1 stop13h 45mMultiple Airlines
mié. 8/134:05 pmPUJ - CLE
1 stop25h 52mMultiple Airlines
Deal found 7/27$324
This CheapOair deal was found by Cheapflights users on 7/28. 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. 8/56:56 pmCLE - MBJ
1 stop13h 59mMultiple Airlines
jue. 8/1410:22 amMBJ - CLE
1 stop6h 35mMultiple Airlines
Deal found 7/28$329

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 julio 28, 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

mié. 9/24

4:34 pm-11:11 am

2 stops18h 37m

San Juan Luis Munoz Marin Intl

sáb. 9/27

3:55 pm-10:50 pm

1 stop6h 55m

$190

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 8/30

12:30 pm-10:07 pm

1 stop9h 37m

San Juan Luis Munoz Marin Intl

sáb. 9/20

7:30 am-3:25 pm

1 stop7h 55m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

dom. 8/10

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

$214

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mié. 10/15

11:00 am-11:57 pm

2 stops12h 57m

San Juan Luis Munoz Marin Intl

mié. 10/22

1:30 pm-8:59 pm

1 stop7h 29m

$228

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

sáb. 9/20

4:45 pm-11:04 am

1 stop18h 19m

San Juan Luis Munoz Marin Intl

vie. 9/26

1:59 am-3:50 pm

2 stops13h 51m

$233

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

lun. 9/1

4:25 pm-11:30 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

vie. 9/26

5:50 am-4:50 pm

1 stop11h 00m

$247

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

jue. 9/25

7:51 pm-9:44 am

1 stop13h 53m

Saint Thomas Island Cyril E King

jue. 10/2

10:49 am-6:56 pm

1 stop8h 07m

$269

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

lun. 8/11

10:00 pm-12:09 pm

2 stops38h 09m

Punta Cana

jue. 8/14

11:25 am-6:30 pm

1 stop7h 05m

$308

ClevelandChristiansted

CLE - STX

CLESTX

Cleveland Hopkins Intl

sáb. 8/23

7:02 pm-11:26 am

1 stop16h 24m

Christiansted Henry Rohlsen

sáb. 8/30

12:57 pm-5:57 pm

1 stop29h 00m

$313

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

lun. 10/20

6:00 am-12:27 pm

1 stop6h 27m

Punta Cana

mié. 10/22

1:48 pm-12:15 am

1 stop10h 27m

$323

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

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, 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 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 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 julio 28, 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.

Weekly flight availability from Cleveland to Caribbean

Explore weekly flight availability from Cleveland to Caribbean. 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 julio 28, 2025.

The most flights from CLE to 0CB 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).

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 julio 28, 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
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,237 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,971 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,893 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,237 reviews

Boarding

8.1

Crew

8.6

Entertainment

7.5

Overall

8.0

Food

7.0

Comfort

8.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Southwest. Other airlines that offer cheap prices include United Airlines from $102 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 - 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 $226, our data indicates the cheapest price to be $96. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $175.

  • 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 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

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 julio 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$362FlexibilityNo cancel feeOn-time65%
FrontierCheapest$145Average$396FlexibilityNo cancel feeOn-time62%
DeltaCheapest$181Average$549FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$203Average$589FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$241Average$610FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$289Average$602FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$319Average$633FlexibilityNo cancel feeOn-time63%

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