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Caribbean Islands

$113+ 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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
dic. 5 — dic. 121
vie. 12/5
vie. 12/12
1 adult, Economy
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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 noviembre 5, 2025.

This United Airlines deal was found by Cheapflights users on 11/2. 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.
sáb. 12/612:33 pmCLE - SJU
2 stops11h 03mUnited Airlines
mié. 12/102:05 amSJU - CLE
1 stop8h 27mUnited Airlines
Deal found 11/2$256
This Kiwi.com deal was found by Cheapflights users on 11/3. 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. 11/177:20 amCLE - SJU
2 stops19h 13mFrontier
lun. 11/249:30 pmSJU - CLE
1 stop26h 00mFrontier
Deal found 11/3$258
This United Airlines deal was found by Cheapflights users on 11/3. 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.
sáb. 11/1511:00 amCLE - SJU
2 stops10h 22mUnited Airlines
vie. 11/212:05 amSJU - CLE
1 stop8h 32mUnited Airlines
Deal found 11/3$259
This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
jue. 11/206:00 amCLE - SJU
1 stop13h 27mMultiple Airlines
dom. 11/233:59 amSJU - CLE
1 stop9h 24mMultiple Airlines
Deal found 11/4$260
This United Airlines deal was found by Cheapflights users on 11/3. 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.
lun. 11/1011:00 amCLE - SJU
1 stop9h 00mUnited Airlines
mar. 11/188:30 amSJU - CLE
2 stops9h 31mUnited Airlines
Deal found 11/3$266
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
mié. 12/34:48 pmCLE - SJU
1 stop9h 02mFrontier
mar. 12/93:55 amSJU - CLE
2 stops32h 12mFrontier
Deal found 11/3$267
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
vie. 12/125:40 amCLE - SJU
2 stops17h 36mMultiple Airlines
jue. 12/189:49 amSJU - CLE
1 stop24h 26mMultiple Airlines
Deal found 11/3$268
This Kiwi.com deal was found by Cheapflights users on 11/3. 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.
vie. 11/213:11 pmCLE - SJU
1 stop22h 02mMultiple Airlines
dom. 11/238:00 amSJU - CLE
1 stop15h 30mMultiple Airlines
Deal found 11/3$270
This American Airlines deal was found by Cheapflights users on 11/4. 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. 12/99:14 amCLE - SJU
1 stop11h 55mAmerican Airlines
vie. 12/122:36 pmSJU - CLE
2 stops10h 13mAmerican Airlines
Deal found 11/4$271
This Delta deal was found by Cheapflights users on 11/3. 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. 11/106:00 amCLE - SJU
1 stop7h 17mDelta
lun. 11/173:32 pmSJU - CLE
1 stop10h 06mDelta
Deal found 11/3$272
This American Airlines deal was found by Cheapflights users on 11/3. 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.
jue. 11/131:10 pmCLE - SJU
2 stops9h 42mAmerican Airlines
jue. 12/42:36 pmSJU - CLE
2 stops9h 06mAmerican Airlines
Deal found 11/3$276
This Kiwi.com deal was found by Cheapflights users on 11/3. 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. 12/16:15 amCLE - SJU
1 stop16h 29mFrontier
dom. 12/71:59 amSJU - CLE
2 stops34h 08mFrontier
Deal found 11/3$277

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 noviembre 5, 2025.

Round-trip from

$256
(United Airlines)

One-way from

$113
(Delta)

Popular in

December

Cheapest in

May

Average price

$383
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. 20% potential increase in price ($80 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 noviembre 5, 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

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

vie. 1/2

6:59 pm-2:28 pm

1 stop18h 29m

Saint Thomas Island Cyril E King

mié. 1/7

3:23 pm-12:26 am

1 stop10h 03m

$294

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

dom. 12/7

6:45 am-11:56 am

1 stop28h 11m

Saint Thomas Island Cyril E King

sáb. 12/13

1:01 pm-9:49 am

1 stop21h 48m

$303

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

mar. 1/27

3:40 pm-12:36 am

1 stop7h 56m

San Juan Luis Munoz Marin Intl

lun. 2/2

2:05 am-8:22 am

1 stop7h 17m

$315

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

jue. 2/19

7:37 pm-12:55 pm

1 stop16h 18m

Oranjestad Reina Beatrix

mié. 2/25

2:10 pm-9:57 pm

1 stop8h 47m

$322

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

vie. 1/30

7:34 pm-12:30 pm

1 stop15h 56m

Oranjestad Reina Beatrix

lun. 2/9

4:35 pm-12:39 am

1 stop9h 04m

$322

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

mar. 12/9

7:00 am-3:00 pm

1 stop7h 00m

Oranjestad Reina Beatrix

mar. 12/16

5:35 pm-9:46 am

1 stop17h 11m

$322

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

jue. 11/13

5:45 am-12:02 pm

1 stop6h 17m

Montego Bay Sangster Intl

mar. 11/18

1:07 pm-11:59 pm

1 stop10h 52m

$324

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

mar. 2/3

7:47 pm-2:00 pm

2 stops17h 13m

Oranjestad Reina Beatrix

mar. 2/10

3:42 pm-10:17 am

2 stops19h 35m

$326

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

vie. 1/30

4:35 pm-12:00 pm

1 stop18h 25m

Oranjestad Reina Beatrix

sáb. 2/7

1:15 pm-9:40 am

2 stops21h 25m

$326

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

jue. 1/29

7:05 am-3:20 pm

1 stop7h 15m

Oranjestad Reina Beatrix

sáb. 2/7

1:15 pm-9:40 am

2 stops21h 25m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $123). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $172). 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 noviembre 5, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 22% on flights from Cleveland to Caribbean Islands by exploring options for tickets in the afternoon.

What is the cheapest day to fly from Cleveland to Caribbean Islands?

Use this chart to determine the cheapest time to fly round-trip from Cleveland to Caribbean Islands. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Cleveland to Caribbean Islands flight should consider departing on Tuesday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

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 noviembre 5, 2025.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Cleveland to Caribbean Islands. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,004 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,039 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Spirit Airlines
6.3
Okay
8,113 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Frontier
5.8
Fair
3,115 reviews
Delta
7.9
Good
8,004 reviews

Crew

8.5

Overall

7.9

Entertainment

7.9

Boarding

8.2

Comfort

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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.

  • How long is the flight from Cleveland to Caribbean Islands?

    There are many flights that can get you from Cleveland to Caribbean Islands in 6h 17m. Fly via United Airlines, Delta, or Spirit Airlines to get the fastest option. Airlines will cover a distance of 1599 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Cleveland to Caribbean Islands one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $113. Users have also found prices from $113 and $117 on United Airlines and Frontier, respectively.

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

    While some choose either Cleveland Hopkins Intl - Oranjestad Reina Beatrix or Cleveland Hopkins Intl - Punta Cana, 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 $471, our data shows the cheapest flight currently is $170. When looking at the most popular route, (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), you can expect to pay $203 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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean Islands (average of $123). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $172). 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 noviembre 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$375FlexibilityNo cancel feeOn-time65%
FrontierCheapest$150Average$402FlexibilityNo cancel feeOn-time62%
DeltaCheapest$168Average$549FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$203Average$571FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$213Average$600FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$589FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$268Average$616FlexibilityNo cancel feeOn-time63%

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