How many flights depart from Cleveland to Caribbean Islands on average per week?

3 flights are operational weekly from Cleveland to Caribbean Islands as of May 2026. The most popular departure day for this route is Tue, with 33% of flights per week taking off on this day.

What airlines fly to Caribbean Islands?

American Airlines, Frontier and Delta are the top three most popular airlines that fly to Caribbean Islands from Cleveland according to our data. American Airlines is the first choice among our users, with 31% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 8 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Cleveland Hopkins Intl to Caribbean Islands?

Frontier, United Airlines, and American Airlines are the most popular carriers operating from Cleveland Hopkins Intl to Caribbean Islands

When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Caribbean Islands?

Prices for flights from Cleveland Hopkins Intl Airport to Caribbean Islands are updated daily.

How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Caribbean Islands?

As of May 2026, there are 6 operators available to choose from for flights from Cleveland Hopkins Intl Airport to Caribbean Islands.

How old do you have to be to fly from Cleveland Hopkins Intl Airport to Caribbean Islands?

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Caribbean Islands.

What documentation or ID do you need to fly to Caribbean Islands?

The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

$96 Cheap Flights from Cleveland to Caribbean Islands in 2026

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Cleveland to Caribbean Islands

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 2:08 am

CLE

SJU

19h 38m

1 stop

7:30 am - 7:04 pm

SJU

CLE

11h 34m

1 stop

$203Frontier

Fri, Jun 5 - Wed, Jun 10

6:30 am - 2:08 am

CLE

SJU

19h 38m

1 stop

9:00 am - 7:29 pm

SJU

CLE

10h 29m

1 stop

$204Frontier

Tue, May 19 - Sun, May 31

7:10 pm - 11:35 am

CLE

STT

16h 25m

2 stops

5:05 pm - 11:59 pm

STT

CLE

6h 54m

1 stop

$325American Airlines

Fri, May 15 - Tue, May 19

6:00 am - 3:34 pm

CLE

MBJ

10h 34m

1 stop

2:22 pm - 12:48 am

MBJ

CLE

9h 26m

1 stop

$372Delta

Mon, May 18 - Fri, May 22

6:00 am - 2:10 pm

CLE

AUA

8h 10m

1 stop

1:55 pm - 11:20 pm

AUA

CLE

9h 25m

1 stop

$375Delta

Tue, May 26 - Fri, May 29

6:00 am - 3:10 pm

CLE

MBJ

10h 10m

1 stop

4:12 pm - 9:34 am

MBJ

CLE

16h 22m

1 stop

$376United Airlines

Mon, Jun 1 - Sat, Jun 6

6:01 am - 11:44 am

CLE

MBJ

6h 43m

1 stop

5:14 pm - 11:12 am

MBJ

CLE

16h 58m

2 stops

$377American Airlines

Tue, Jun 30 - Tue, Jul 7

6:00 am - 3:43 pm

CLE

STT

9h 43m

1 stop

4:45 pm - 11:59 pm

STT

CLE

7h 14m

1 stop

$405United Airlines

Fri, May 15 - Tue, May 19

6:20 am - 12:50 pm

CLE

PLS

6h 30m

1 stop

2:10 pm - 11:59 pm

PLS

CLE

9h 49m

1 stop

$499JetBlue

Thu, Jun 11 - Wed, Jun 17

6:25 am - 12:50 pm

CLE

PLS

6h 25m

1 stop

2:10 pm - 11:59 pm

PLS

CLE

9h 49m

1 stop

$504JetBlue

Tue, Jun 16 - Tue, Jun 23

Frontier flights from Cleveland to Caribbean Islands

Our best Frontier deals on Cleveland to Caribbean Islands flight tickets

Frontier

Jun 5

CLE6:30 amCleveland Hopkins Intl

19h 38m

1 stop

SJU2:08 amSan Juan Luis Munoz Marin Intl

Jun 10

SJU7:30 amSan Juan Luis Munoz Marin Intl

11h 34m

1 stop

CLE7:04 pmCleveland Hopkins Intl

$203

Frontier

May 19

CLE6:30 amCleveland Hopkins Intl

19h 38m

1 stop

SJU2:08 amSan Juan Luis Munoz Marin Intl

May 31

SJU9:00 amSan Juan Luis Munoz Marin Intl

10h 29m

1 stop

CLE7:29 pmCleveland Hopkins Intl

$204

Frontier

May 20

CLE3:49 pmCleveland Hopkins Intl

25h 37m

1 stop

SJU5:26 pmSan Juan Luis Munoz Marin Intl

May 23

SJU9:45 pmSan Juan Luis Munoz Marin Intl

26h 50m

1 stop

CLE12:35 amCleveland Hopkins Intl

$207

Air Canada flights from Cleveland to Caribbean Islands

Our best Air Canada deals on Cleveland to Caribbean Islands flight tickets

Air Canada

Oct 17

CLE7:00 pmCleveland Hopkins Intl

20h 25m

1 stop

BGI3:25 pmBridgetown Grantley Adams Intl

Oct 22

BGI4:20 pmBridgetown Grantley Adams Intl

21h 47m

1 stop

CLE2:07 pmCleveland Hopkins Intl

$388

Air Canada

Oct 17

CLE2:45 pmCleveland Hopkins Intl

24h 40m

2 stops

BGI3:25 pmBridgetown Grantley Adams Intl

Oct 22

BGI4:20 pmBridgetown Grantley Adams Intl

21h 47m

1 stop

CLE2:07 pmCleveland Hopkins Intl

$392

Air Canada

Sep 29

CLE2:45 pmCleveland Hopkins Intl

24h 40m

2 stops

BGI3:25 pmBridgetown Grantley Adams Intl

Oct 6

BGI4:20 pmBridgetown Grantley Adams Intl

26h 03m

2 stops

CLE6:23 pmCleveland Hopkins Intl

$395

momondo Fare Finder

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

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 6/5

6:30 am-2:08 am

1 stop19h 38m

San Juan Luis Munoz Marin Intl

Wed 6/10

7:30 am-7:04 pm

1 stop11h 34m

$203

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 5/19

6:30 am-2:08 am

1 stop19h 38m

San Juan Luis Munoz Marin Intl

Sun 5/31

9:00 am-7:29 pm

1 stop10h 29m

$204

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Fri 5/15

7:10 pm-11:35 am

2 stops16h 25m

Saint Thomas Island Cyril E King

Tue 5/19

5:05 pm-11:59 pm

1 stop6h 54m

$325

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Mon 5/18

6:00 am-3:34 pm

1 stop10h 34m

Montego Bay Sangster Intl

Fri 5/22

2:22 pm-12:48 am

1 stop9h 26m

$372

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Tue 5/26

6:00 am-2:10 pm

1 stop8h 10m

Oranjestad Reina Beatrix

Fri 5/29

1:55 pm-11:20 pm

1 stop9h 25m

$375

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Mon 6/1

6:00 am-3:10 pm

1 stop10h 10m

Montego Bay Sangster Intl

Sat 6/6

4:12 pm-9:34 am

1 stop16h 22m

$376

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Tue 6/30

6:01 am-11:44 am

1 stop6h 43m

Montego Bay Sangster Intl

Tue 7/7

5:14 pm-11:12 am

2 stops16h 58m

$377

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Fri 5/15

6:00 am-3:43 pm

1 stop9h 43m

Saint Thomas Island Cyril E King

Tue 5/19

4:45 pm-11:59 pm

1 stop7h 14m

$405

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Thu 6/11

6:20 am-12:50 pm

1 stop6h 30m

Providenciales

Wed 6/17

2:10 pm-11:59 pm

1 stop9h 49m

$499

Quickest round-trip

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Tue 6/16

6:25 am-12:50 pm

1 stop6h 25m

Providenciales

Tue 6/23

2:10 pm-11:59 pm

1 stop9h 49m

$504

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Cleveland to Caribbean Islands

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean Islands?

The month of September is, on average, the cheapest month to fly to Caribbean Islands from Cleveland, with most prices found around $119. The month of October is another great option to travel to Caribbean Islands, with average flight prices from Cleveland averaging around $151.

What is the cheapest day to depart on your flight to Caribbean Islands?

The cheapest day to depart from Cleveland to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets for as low as $230. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $347. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean Islands.

What is the cheapest time of day to depart on your flight to Caribbean Islands?

According to our data, the cheapest time of day to fly to Caribbean Islands is in the afternoon. momondo users have found flights departing from Cleveland to Caribbean Islands in the afternoon for as low as $274. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the morning because they tend to be around $283. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Cleveland Hopkins Intl to Caribbean Islands flight route?

Fly from Cleveland Hopkins Intl to San Juan Luis Munoz Marin Intl for the best Cleveland Hopkins Intl - Caribbean Islands flight prices

How far in advance should I book a flight from Cleveland to Caribbean Islands?

You are more likely to see cheaper flights to Caribbean Islands from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $333 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Cleveland for as low as $265 on momondo.

Can stopping save me money on Cleveland to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Cleveland to Caribbean Islands.

Cheap Cleveland to Caribbean Islands flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Cleveland to Caribbean Islands

Fastest flight time	4h 14m
Direct flights	Mon, Wed and Fri
Airports in Caribbean Islands	99 airports

The fastest flight from Cleveland to Caribbean Islands takes 4h 14m

Direct flights go from Cleveland to Caribbean Islands on Monday, Wednesday and Friday. There are no airlines offering direct flights.

There are 99 airports in Caribbean Islands. From Cleveland there are direct flights to Punta Cana (PUJ).

Search flight deals

Frequently asked questions about flying from Cleveland to Caribbean Islands

When did momondo last update prices for flights from Cleveland Hopkins Intl Airport to Caribbean Islands?
Prices for flights from Cleveland Hopkins Intl Airport to Caribbean Islands are updated daily.
How many operators does momondo search for flights from Cleveland Hopkins Intl Airport to Caribbean Islands?
As of May 2026, there are 6 operators available to choose from for flights from Cleveland Hopkins Intl Airport to Caribbean Islands.
How old do you have to be to fly from Cleveland Hopkins Intl Airport to Caribbean Islands?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Caribbean Islands.
What documentation or ID do you need to fly to Caribbean Islands?
The required travel and health documents for your Caribbean Islands trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Caribbean Islands. We recommend that you seek guidance from your airline or a reliable third party such as IATA.
What is the most popular plane model from Cleveland to Caribbean Islands?
Based on momondo bookings for flights between Cleveland and Caribbean Islands, the leading plane model is Airbus A320neo, making up 16.25% of the total bookings. Other popular models include Airbus A321neo with 16.06%, Boeing 737 MAX 8 with 12.65%, and Boeing 737-800 with 12.35%.

Best airlines flying from Cleveland to Caribbean Islands

Compare and see reviews for airlines that fly from Cleveland to Caribbean Islands with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $102	Free Cancellation	Rating 7.9 8,460 reviews	Search Delta flights
JetBlue	PriceFrom $160	Free Cancellation	Rating 7.1 2,977 reviews	Search JetBlue flights
Frontier	PriceFrom $170	Free Cancellation	Rating 5.6 2,965 reviews	Search Frontier flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 9,683 reviews	Search United Airlines flights
American Airlines	PriceFrom $225	Free Cancellation	Rating 7.1 11,667 reviews	Search American Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 7.9 4,305 reviews	Search Southwest flights

Why use momondo?

Why should I use momondo to find a flight deal from Cleveland to Caribbean Islands?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Cleveland to Caribbean Islands for you.

Can I find flights from Cleveland to Caribbean Islands with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Caribbean Islands from Cleveland with this policy.

How can momondo help me find flights from Cleveland to Caribbean Islands?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Cleveland.

I’m not ready to book a flight from Cleveland to Caribbean Islands right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Cleveland to Caribbean Islands flights. All you need is a valid email address and we will do the rest; it is that quick and easy.