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Caribbean

$87+ 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 2/24. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap 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 January 26, 2026.

This Priceline deal was found by Cheapflights users on 1/24. 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.
Wed 4/86:00 am
CLE
-
BQN
1 stop19h 53m
Frontier
Mon 4/139:14 pm
BQN
-
CLE
1 stop21h 42m
Frontier
Deal found 1/24$182
This CheapOair deal was found by Cheapflights users on 1/24. 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.
Tue 2/241:55 pm
CLE
-
BQN
1 stop12h 02m
Frontier
Tue 3/33:59 am
BQN
-
CLE
1 stop20h 10m
Frontier
Deal found 1/24$197
This Flightnetwork deal was found by Cheapflights users on 1/25. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2111:50 am
CLE
-
SJU
1 stop6h 53m
Frontier
Wed 2/2511:07 am
SJU
-
CLE
1 stop13h 02m
Frontier
Deal found 1/25$198
This eDestinos deal was found by Cheapflights users on 1/24. 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.
Thu 3/54:29 pm
CLE
-
SJU
1 stop9h 24m
Frontier
Wed 3/116:39 pm
SJU
-
CLE
1 stop24h 52m
Frontier
Deal found 1/24$199
This Frontier deal was found by Cheapflights users on 1/24. 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 3/21:33 pm
CLE
-
SJU
1 stop12h 20m
Frontier
Sat 3/74:41 pm
SJU
-
CLE
1 stop10h 01m
Frontier
Deal found 1/24$201
This Frontier deal was found by Cheapflights users on 1/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/48:00 am
CLE
-
SJU
1 stop6h 26m
Frontier
Wed 2/1111:07 am
SJU
-
CLE
1 stop13h 02m
Frontier
Deal found 1/26$203
This Priceline deal was found by Cheapflights users on 1/25. 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.
Tue 4/75:20 pm
CLE
-
BQN
1 stop8h 33m
Frontier
Mon 4/202:38 am
BQN
-
CLE
1 stop11h 30m
Frontier
Deal found 1/25$203
This Kiwi.com deal was found by Cheapflights users on 1/25. 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.
Mon 2/97:30 am
CLE
-
SJU
1 stop6h 56m
Frontier
Fri 2/137:09 pm
SJU
-
CLE
1 stop18h 16m
Frontier
Deal found 1/25$204
This Frontier deal was found by Cheapflights users on 1/24. 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 2/23:25 pm
CLE
-
SJU
1 stop7h 34m
Frontier
Sat 2/74:36 pm
SJU
-
CLE
1 stop9h 07m
Frontier
Deal found 1/24$205
This Frontier deal was found by Cheapflights users on 1/25. 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.
Sat 2/77:10 am
CLE
-
SJU
1 stop8h 50m
Frontier
Thu 2/126:00 am
SJU
-
CLE
1 stop7h 38m
Frontier
Deal found 1/25$207
This eDestinos deal was found by Cheapflights users on 1/24. 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.
Thu 3/54:29 pm
CLE
-
SJU
1 stop9h 24m
Frontier
Thu 3/126:30 am
SJU
-
CLE
1 stop12h 14m
Frontier
Deal found 1/24$208
This Priceline deal was found by Cheapflights users on 1/23. 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.
Tue 3/247:14 pm
CLE
-
SJU
1 stop13h 40m
Frontier
Tue 4/76:30 am
SJU
-
CLE
1 stop17h 43m
Frontier
Deal found 1/23$209

Find flight deals from Cleveland to Caribbean

Keep the following information in mind while searching for Cleveland to Caribbean flight deals. Data was last updated January 26, 2026.

Round-trip from

$182
(Priceline)

One-way from

$87
(Expedia)

Popular in

December

Cheapest in

May

Average price

$326

Good round-trip deal

$421 or less

Good one-way deal

$243 or less
From Cleveland Hopkins Intl to Caribbean
Search Deals
One-way flight from Cleveland Hopkins Intl to Caribbean
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($77 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 January 2026
Search Deals
Price to beat on a round-trip flight from Cleveland Hopkins Intl to Caribbean.
Search Deals
Price to beat on a one-way flight from Cleveland Hopkins Intl to Caribbean.
Search Deals

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 January 26, 2026.
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

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Wed 3/4

8:40 am-2:57 am

1 stop17h 17m

Aguadilla Borinquen

Mon 4/6

2:43 am-12:13 am

1 stop21h 30m

$182

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Wed 4/8

6:00 am-1:53 am

1 stop19h 53m

Aguadilla Borinquen

Mon 4/13

9:14 pm-11:40 pm

1 stop26h 26m

$182

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Tue 2/24

1:55 pm-2:57 am

1 stop12h 02m

Aguadilla Borinquen

Tue 3/3

3:59 am-11:09 pm

1 stop20h 10m

$197

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Tue 3/24

7:14 pm-1:42 am

1 stop6h 28m

Aguadilla Borinquen

Mon 4/6

2:43 am-12:13 am

1 stop21h 30m

$228

ClevelandAguadilla

CLE - BQN

CLEBQN

Cleveland Hopkins Intl

Wed 2/18

4:47 pm-2:57 am

1 stop9h 10m

Aguadilla Borinquen

Sat 2/21

3:58 am-7:56 am

1 stop28h 58m

$238

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Tue 3/3

12:30 pm-4:34 pm

1 stop27h 04m

Saint Thomas Island Cyril E King

Sat 3/7

5:40 pm-1:42 am

1 stop9h 02m

$240

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Tue 2/24

12:30 pm-4:34 pm

1 stop27h 04m

Saint Thomas Island Cyril E King

Tue 3/3

5:40 pm-7:14 pm

2 stops26h 34m

$241

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Tue 4/7

6:26 pm-3:28 pm

1 stop21h 02m

Saint Thomas Island Cyril E King

Tue 4/14

4:35 pm-4:40 pm

1 stop24h 05m

$245

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 4/19

6:00 am-12:34 pm

1 stop6h 34m

San Juan Luis Munoz Marin Intl

Thu 4/30

7:40 am-3:19 pm

1 stop7h 39m

$246

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 3/30

1:58 pm-11:15 pm

1 stop9h 17m

San Juan Luis Munoz Marin Intl

Sun 4/5

2:07 pm-11:50 pm

1 stop9h 43m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/24

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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $103). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $199). 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.

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 January 26, 2026.
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
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,111 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,199 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,189 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Frontier
5.7
Fair
3,058 reviews
Southwest
8.0
Very good
4,268 reviews

Boarding

8.1

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.

  • How long is the flight from Cleveland to Caribbean?

    Frontier, Spirit Airlines, and United Airlines can get you from Cleveland to Caribbean in just under 6h 34m. Your travel time can differ by up to 14h 28m. Airlines will cover a distance of 1841 mi. This flight may include one or multiple stops.

  • 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 $57 on Spirit Airlines. Other airlines that offer cheap prices include Frontier from $81 and American Airlines from $88 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 $368, our data indicates the cheapest price to be $147. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $202.

  • 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, November is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $103). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $199). 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$63Average$333FlexibilityNo cancel feeOn-time65%
DeltaCheapest$106Average$530FlexibilityNo cancel feeOn-timeN/A
FrontierCheapest$154Average$416FlexibilityNo cancel feeOn-time62%
JetBlueCheapest$154Average$547FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$216Average$587FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$572FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$245Average$643FlexibilityNo cancel feeOn-time63%

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