Caribbean

$119+ 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 8/4. Fares are subject to change and may not be available on all flights or dates of travel.
CLE — SJU
Jul 10 — Jul 171
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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 June 10, 2026.

This American Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/139:23 am
CLE
-
SJU
1 stop14h 36m
American Airlines
Fri 8/216:00 am
SJU
-
CLE
1 stop17h 50m
American Airlines
Deal found 6/10$238
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/269:43 am
CLE
-
SJU
1 stop13h 32m
American Airlines
Tue 9/13:28 pm
SJU
-
CLE
1 stop8h 16m
American Airlines
Deal found 6/10$243
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/262:59 pm
CLE
-
SJU
1 stop24h 59m
Frontier
Tue 9/16:41 pm
SJU
-
CLE
1 stop28h 31m
Frontier
Deal found 6/5$262
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Tue 8/111:54 pm
CLE
-
SJU
1 stop10h 47m
Frontier
Wed 8/266:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 6/5$269
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/234:34 pm
CLE
-
SJU
1 stop7h 49m
Frontier
Wed 8/266:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 6/5$274
This Kiwi.com deal was found by Cheapflights users on 6/7. 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 8/194:34 pm
CLE
-
SJU
1 stop7h 49m
Frontier
Wed 8/266:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 6/7$275
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Sat 8/154:28 pm
CLE
-
SJU
1 stop8h 00m
Frontier
Sun 8/306:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 6/5$276
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Sat 8/12:04 pm
CLE
-
SJU
1 stop10h 37m
Frontier
Thu 8/66:00 am
SJU
-
CLE
1 stop8h 36m
Frontier
Deal found 6/7$278
This Kiwi.com deal was found by Cheapflights users on 6/10. 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 8/262:59 pm
CLE
-
SJU
1 stop24h 59m
Frontier
Sun 8/306:00 am
SJU
-
CLE
1 stop8h 38m
Frontier
Deal found 6/10$280
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/56:33 pm
CLE
-
SJU
1 stop30h 08m
Frontier
Tue 8/116:00 am
SJU
-
CLE
1 stop16h 57m
Frontier
Deal found 6/5$281
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 8/267:45 am
CLE
-
SJU
1 stop8h 13m
Frontier
Fri 8/285:01 pm
SJU
-
CLE
1 stop7h 43m
Frontier
Deal found 6/5$285
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Tue 10/65:00 am
CLE
-
MBJ
1 stop9h 05m
American Airlines
Fri 10/1610:50 am
MBJ
-
CLE
1 stop12h 15m
American Airlines
Deal found 6/8$352

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 June 10, 2026.

Round-trip from

$238
(American Airlines)

One-way from

$119
(American Airlines)

Popular in

December

Cheapest in

May

Average price

$394

Good round-trip deal

$585 or less
From Cleveland Hopkins Intl to Caribbean
One-way flight from Cleveland Hopkins Intl to Caribbean
Highest demand for flights based on searches. 12% potential increase in price ($49 potential increase over avg. RT price).
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Average for round-trip flights in June 2026
Price to beat on a round-trip flight from Cleveland Hopkins Intl to Caribbean.

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 June 10, 2026.
Use the filters below to find and compare flights from Cleveland to Caribbean that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 10/29

7:00 am-1:40 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Thu 11/12

2:05 am-10:58 am

1 stop9h 53m

$346

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 9/4

12:35 pm-10:29 pm

1 stop9h 54m

San Juan Luis Munoz Marin Intl

Mon 9/7

7:30 am-4:33 pm

1 stop9h 03m

$346

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 9/4

11:00 am-10:50 pm

1 stop11h 50m

San Juan Luis Munoz Marin Intl

Mon 9/7

5:30 am-12:15 pm

1 stop6h 45m

$346

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 9/30

9:00 am-8:38 pm

2 stops11h 38m

San Juan Luis Munoz Marin Intl

Mon 10/5

3:56 pm-11:59 pm

1 stop8h 03m

$346

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 9/4

11:00 am-10:29 pm

1 stop11h 29m

San Juan Luis Munoz Marin Intl

Tue 9/8

5:45 pm-12:36 am

1 stop6h 51m

$346

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 10/29

6:15 am-4:30 pm

2 stops10h 15m

San Juan Luis Munoz Marin Intl

Fri 11/13

11:20 am-8:15 pm

2 stops9h 55m

$355

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 10/15

11:30 am-12:35 am

1 stop13h 05m

San Juan Luis Munoz Marin Intl

Thu 10/22

5:20 pm-12:10 am

1 stop6h 50m

$365

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 12/5

7:00 am-2:40 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Wed 12/9

2:05 am-11:41 am

2 stops10h 36m

$367

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 10/31

7:00 am-1:40 pm

1 stop6h 40m

San Juan Luis Munoz Marin Intl

Sat 11/7

8:30 am-6:20 pm

2 stops10h 50m

$368

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Tue 9/1

5:26 am-11:44 am

1 stop7h 18m

Montego Bay Sangster Intl

Wed 9/30

1:25 pm-12:43 am

1 stop10h 18m

$372

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/8

Showing 1-10 of 60 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Cleveland to Caribbean (average of $138). Flying from Cleveland to Caribbean in October is currently the most expensive (average of $1,030). 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 June 10, 2026.

It’s typically best to fly out from Cleveland to Caribbean in the afternoon. Doing so could potentially save you 67% on the flight price compared to flying at noon, which is usually more expensive.

How far ahead should I book a flight from Cleveland to Caribbean?

Booking 16 days in advance of your planned departure date is, on average, the best time to get cheap flights from Cleveland to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.

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 June 10, 2026.
See what other customers who have flown with Southwest,Delta, andUnited 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.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Food

7.0

Crew

8.6

Overall

7.9

Reviews

1 / 20
8.0
Excellent

La Tracimeldamarcos,Jun 2026

LAX - SLC

The second flight was not as comfortable as the first as we had to change planes to what seemed to be a slightly older aircraft. The seats weren’t as comfortable as the other plane. But it wasn’t bad.

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?

    United Airlines, Delta, and Southwest can get you from Cleveland to Caribbean in just under 6h 40m. Your travel time can differ by up to 5h 10m. 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 $94 on Frontier. Other airlines that offer cheap prices include Southwest from $102 and Delta from $102 one-way.

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

  • 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 $138). Flying from Cleveland to Caribbean in October is currently the most expensive (average of $1,030). 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

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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.

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 June 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$114Average$523FlexibilityNo cancel feeOn-timeN/A
Air CanadaCheapest$151Average$388FlexibilityNo cancel feeOn-time67%
JetBlueCheapest$160Average$534FlexibilityNo cancel feeOn-time62%
FrontierCheapest$181Average$452FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$225Average$547FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$225Average$605FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$609FlexibilityNo cancel feeOn-time63%

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