HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$110+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Cleveland to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 28, 2025.

Round-trip from

$250
(Kiwi.com)

One-way from

$110
(Priceline)

Popular in

December

Cheapest in

May

Average price

$305

Good round-trip deal

$525 or less

Good one-way deal

$276 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. 20% potential increase in price ($82 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
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

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 October 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/186:00 amCLE - SJU
1 stop8h 40mUnited Airlines
Mon 11/242:05 amSJU - CLE
1 stop8h 32mUnited Airlines
Deal found 10/26$251
This Frontier deal was found by Cheapflights users on 10/26. 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.
Sun 11/167:20 amCLE - SJU
1 stop6h 59mFrontier
Sat 11/223:23 pmSJU - CLE
1 stop8h 07mFrontier
Deal found 10/26$253
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 12/74:38 pmCLE - SJU
1 stop15h 59mMultiple Airlines
Fri 12/124:10 amSJU - CLE
1 stop10h 35mMultiple Airlines
Deal found 10/27$258
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/131:35 pmCLE - SJU
1 stop10h 57mFrontier
Sat 11/159:00 amSJU - CLE
2 stops15h 57mFrontier
Deal found 10/27$259
This Frontier deal was found by Cheapflights users on 10/26. 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.
Mon 11/107:20 amCLE - SJU
1 stop6h 54mFrontier
Mon 11/243:23 pmSJU - CLE
1 stop8h 07mFrontier
Deal found 10/26$260
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Wed 12/316:59 pmCLE - STT
1 stop18h 29mMultiple Airlines
Wed 1/73:23 pmSTT - CLE
1 stop17h 30mMultiple Airlines
Deal found 10/27$262
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/177:20 amCLE - SJU
1 stop6h 59mFrontier
Mon 11/243:23 pmSJU - CLE
1 stop8h 07mFrontier
Deal found 10/27$263
This Southwest deal was found by Cheapflights users on 10/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/811:50 amCLE - SJU
1 stop10h 25mSouthwest
Wed 11/124:40 pmSJU - CLE
1 stop6h 25mSouthwest
Deal found 10/26$265
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:15 amCLE - SJU
1 stop9h 21mUnited Airlines
Mon 11/104:52 pmSJU - CLE
1 stop8h 06mUnited Airlines
Deal found 10/27$266
This Frontier deal was found by Cheapflights users on 10/27. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/157:14 pmCLE - SJU
2 stops19h 05mFrontier
Mon 11/243:23 pmSJU - CLE
1 stop8h 07mFrontier
Deal found 10/27$268
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 11/97:20 amCLE - SJU
2 stops15h 58mFrontier
Thu 11/209:30 pmSJU - CLE
1 stop26h 00mFrontier
Deal found 10/27$269
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Sun 11/96:00 amCLE - SJU
1 stop18h 32mFrontier
Fri 11/219:30 pmSJU - CLE
1 stop26h 00mFrontier
Deal found 10/27$270

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 October 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

Sat 11/8

11:50 am-11:15 pm

1 stop10h 25m

San Juan Luis Munoz Marin Intl

Wed 11/12

4:40 pm-10:05 pm

1 stop6h 25m

$265

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 11/17

7:20 am-2:54 am

2 stops18h 34m

San Juan Luis Munoz Marin Intl

Mon 11/24

3:23 pm-10:30 pm

1 stop8h 07m

$268

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 11/9

5:22 am-2:10 pm

1 stop7h 48m

San Juan Luis Munoz Marin Intl

Fri 11/14

7:00 am-5:22 pm

1 stop11h 22m

$272

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 11/15

11:21 am-11:13 pm

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Tue 11/18

7:15 am-4:58 pm

1 stop10h 43m

$272

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 11/11

12:01 pm-11:56 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Tue 11/18

7:15 am-4:58 pm

1 stop10h 43m

$292

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Sun 11/9

5:45 am-3:35 pm

1 stop8h 50m

Oranjestad Reina Beatrix

Thu 11/13

4:40 pm-11:59 pm

1 stop8h 19m

$297

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 12/9

1:10 pm-12:35 am

2 stops10h 25m

San Juan Luis Munoz Marin Intl

Sat 12/13

5:40 am-3:40 pm

2 stops11h 00m

$309

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 11/8

6:00 am-9:26 pm

2 stops14h 26m

San Juan Luis Munoz Marin Intl

Tue 11/11

2:05 am-1:14 pm

2 stops12h 09m

$315

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Wed 12/31

6:59 pm-2:28 pm

1 stop18h 29m

Saint Thomas Island Cyril E King

Tue 1/6

12:46 pm-12:26 am

2 stops12h 40m

$315

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 1/21

8:49 am-9:26 pm

2 stops11h 37m

San Juan Luis Munoz Marin Intl

Mon 1/26

2:05 am-8:22 am

1 stop7h 17m

$315

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 60 results
1
2
3
...
6

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 $123). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $171). 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 October 28, 2025.

It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 22% on the flight price compared to flying in the morning, which is usually more expensive.

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

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

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

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 October 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
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Frontier
5.8
Fair
3,124 reviews
Southwest
8.0
Very good
4,240 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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?

    Southwest, Frontier, and Delta can get you from Cleveland to Caribbean in just under 7h 48m. Your travel time can differ by up to 10h 46m. 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 $113 on United Airlines. Other airlines that offer cheap prices include American Airlines from $113 and Spirit Airlines from $125 one-way.

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

    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.

  • What are the cheapest flights from Cleveland to Caribbean?

    Looking for the cheapest flight from Cleveland to Caribbean? While on average our users pay $493, our data indicates the cheapest price to be $170. The most popular route (Cleveland Hopkins Intl - San Juan Luis Munoz Marin Intl), is priced around $205.

  • 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 $123). Flying from Cleveland to Caribbean in December is currently the most expensive (average of $171). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Cleveland to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Detroit to Cancún flights
Cleveland to Orlando flights
Detroit to Orlando flights
Detroit to John F Kennedy Intl flights
Cleveland to Las Vegas flights
Detroit to Fort Lauderdale flights
Detroit to Las Vegas flights
Detroit to Dallas/Fort Worth flights
Detroit to Los Angeles flights
Detroit to Miami flights
Detroit to Sky Harbor Intl flights
Cleveland to LaGuardia flights
Cincinnati to Orlando flights
Cincinnati to LaGuardia flights
Detroit to LaGuardia flights
Cincinnati to John F Kennedy Intl flights
Cleveland to John F Kennedy Intl flights
Cleveland to Fort Lauderdale flights
Detroit to Newark flights
Detroit to Denver flights
Cleveland to Fort Myers flights
Cincinnati to Fort Lauderdale flights
Detroit to Fort Myers flights
Cincinnati to Las Vegas flights
Akron to Orlando flights
Columbus to Newark flights
Detroit to Dulles Intl flights
Cleveland to Cancún flights
Columbus to John F Kennedy Intl flights
Detroit to Baltimore flights
Cleveland to Newark flights
Detroit to Reagan-National flights
Cleveland to Tampa flights
Cleveland to Sky Harbor Intl flights
Columbus to LaGuardia flights
Pittsburgh to Fort Lauderdale flights
Pittsburgh to John F Kennedy Intl flights
Detroit to Tampa flights
Cincinnati to Newark flights
Cleveland to Dallas/Fort Worth flights
Pittsburgh to Orlando flights
Detroit to Atlanta flights
Detroit to Boston flights
Detroit to Luis Munoz Marin Intl flights
Cincinnati to Denver flights
Detroit to New Orleans flights
Columbus to Orlando flights
Cleveland to Hobby flights
Cincinnati to Dallas/Fort Worth flights
Pittsburgh to LaGuardia flights

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$118Average$376FlexibilityNo cancel feeOn-time65%
FrontierCheapest$150Average$402FlexibilityNo cancel feeOn-time62%
DeltaCheapest$168Average$549FlexibilityNo cancel feeOn-timeN/A
JetBlueCheapest$193Average$573FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$210Average$599FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$225Average$589FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$267Average$616FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.