Caribbean Islands

$96+ 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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
May 22 — May 291
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Cheap 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 April 22, 2026.

This Super.com deal was found by Cheapflights users on 4/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/1512:55 pm
CLE
-
SJU
1 stop11h 02m
Frontier
Wed 5/206:41 pm
SJU
-
CLE
1 stop29h 54m
Frontier
Deal found 4/17$200
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:18 pm
CLE
-
SJU
1 stop27h 22m
Frontier
Tue 6/24:46 pm
SJU
-
CLE
1 stop6h 58m
Frontier
Deal found 4/18$201
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:18 pm
CLE
-
SJU
1 stop27h 22m
Frontier
Sun 5/319:00 am
SJU
-
CLE
1 stop10h 29m
Frontier
Deal found 4/18$202
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/66:33 pm
CLE
-
SJU
1 stop29h 24m
Frontier
Sun 5/106:00 am
SJU
-
CLE
1 stop17h 12m
Frontier
Deal found 4/20$203
This CheapOair deal was found by Cheapflights users on 4/18. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/237:45 am
CLE
-
SJU
1 stop8h 10m
Frontier
Sun 5/316:00 am
SJU
-
CLE
1 stop8h 42m
Frontier
Deal found 4/18$204
This Super.com deal was found by Cheapflights users on 4/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/169:57 pm
CLE
-
SJU
1 stop10h 07m
Frontier
Tue 6/166:00 am
SJU
-
CLE
1 stop16h 54m
Frontier
Deal found 4/20$206
This Frontier deal was found by Cheapflights users on 4/20. 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.
Fri 6/59:57 pm
CLE
-
SJU
1 stop10h 07m
Frontier
Sat 6/63:58 pm
SJU
-
CLE
1 stop7h 51m
Frontier
Deal found 4/20$207
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:29 pm
CLE
-
SJU
1 stop11h 39m
Frontier
Tue 6/96:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 4/21$210
This eDestinos deal was found by Cheapflights users on 4/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/274:28 pm
CLE
-
SJU
1 stop7h 15m
Frontier
Mon 5/411:07 am
SJU
-
CLE
1 stop9h 48m
Frontier
Deal found 4/17$211
This Frontier deal was found by Cheapflights users on 4/17. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/17:45 am
CLE
-
SJU
1 stop8h 10m
Frontier
Sat 6/68:13 pm
SJU
-
CLE
1 stop11h 35m
Frontier
Deal found 4/17$212
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/225:18 pm
CLE
-
SJU
1 stop27h 22m
Frontier
Mon 6/16:41 pm
SJU
-
CLE
1 stop28h 18m
Frontier
Deal found 4/18$213
This Expedia deal was found by Cheapflights users on 4/19. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:40 am
CLE
-
PUJ
1 stop7h 45m
Frontier
Mon 8/1011:42 am
PUJ
-
CLE
1 stop11h 30m
Frontier
Deal found 4/19$251

Find 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 April 22, 2026.

Round-trip from

$200
(eDestinos)

One-way from

$96
(eDestinos)

Popular in

December

Cheapest in

May

Average price

$303
From Cleveland Hopkins Intl to Caribbean Islands
One-way flight from Cleveland Hopkins Intl to Caribbean Islands
Highest demand for flights based on searches. 15% potential increase in price ($59 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 April 2026

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 April 22, 2026.
Use the filters below to find and compare flights from Cleveland to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Mon 5/4

6:00 am-2:49 pm

1 stop8h 49m

Saint Thomas Island Cyril E King

Fri 5/8

2:30 pm-12:26 am

1 stop9h 56m

$290

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 6/28

12:39 pm-10:27 pm

1 stop9h 48m

San Juan Luis Munoz Marin Intl

Sat 7/4

5:56 pm-12:47 am

1 stop6h 51m

$316

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 4/25

1:53 pm-8:24 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Wed 4/29

7:30 am-6:42 pm

1 stop11h 12m

$316

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Fri 8/14

6:00 am-3:34 pm

1 stop10h 34m

Montego Bay Sangster Intl

Tue 8/18

4:59 pm-12:36 am

1 stop6h 37m

$352

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Mon 7/6

7:30 pm-1:30 pm

1 stop19h 00m

Montego Bay Sangster Intl

Fri 7/10

2:23 pm-9:12 am

1 stop17h 49m

$359

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Tue 5/26

8:15 am-4:40 pm

1 stop8h 25m

Oranjestad Reina Beatrix

Fri 5/29

1:50 pm-10:35 pm

1 stop8h 45m

$375

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Tue 5/19

6:00 am-2:10 pm

1 stop8h 10m

Oranjestad Reina Beatrix

Tue 5/26

3:25 pm-12:32 am

1 stop9h 07m

$375

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Mon 5/18

6:00 am-2:10 pm

1 stop8h 10m

Oranjestad Reina Beatrix

Tue 5/26

3:25 pm-12:32 am

1 stop9h 07m

$375

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 5/4

12:40 pm-11:25 pm

2 stops10h 45m

San Juan Luis Munoz Marin Intl

Fri 5/8

5:05 am-3:05 pm

2 stops10h 00m

$398

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 5/8

8:30 am-9:24 pm

2 stops12h 54m

San Juan Luis Munoz Marin Intl

Tue 5/12

7:20 am-8:44 pm

2 stops13h 24m

$406

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/17

Showing 1-10 of 60 resultsSorted by cheapest first
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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 $119). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $1,617). 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 April 22, 2026.

Unlike at noon, when flights are generally more expensive, you can save up to 70% on flights from Cleveland to Caribbean Islands by exploring options for tickets in the afternoon.

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 April 22, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

Comfort

8.0

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 8h 25m. Fly via American Airlines, Delta, or United Airlines to get the fastest option. Airlines will cover a distance of 2120 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 Frontier. According to our data, you can fly for as low as $91. Users have also found prices from $102 and $102 on American Airlines and Southwest, respectively.

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

  • 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 $119). Flying from Cleveland to Caribbean Islands in December is currently the most expensive (average of $1,617). 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 6 airlines flying from Cleveland to Caribbean Islands

Discover the top 6 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 April 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$102Average$516FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$160Average$540FlexibilityNo cancel feeOn-time62%
FrontierCheapest$170Average$441FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$218Average$585FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$544FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$246Average$568FlexibilityNo cancel feeOn-time63%

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