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 34% of people opting to fly with this airline when traveling to Caribbean Islands. Keep in mind that there are 7 different airlines that fly to Caribbean Islands on a routine basis, so you have a few additional options to choose from.

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 June 2026. The most popular departure day for this route is Tue, with 33% of flights per week taking off on this day.

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

American Airlines, JetBlue, and Frontier 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 June 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.

$107 Cheap Flights from Cleveland to Caribbean Islands in 2026

Discover deals from 900+ travel sites with momondo.

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.

5:30 am - 2:44 pm

CLE

SJU

9h 14m

1 stop

1:00 am - 10:39 am

SJU

CLE

9h 39m

1 stop

$233United Airlines

Sat, Sep 12 - Sat, Sep 12

8:18 am - 3:07 pm

CLE

SJU

6h 49m

1 stop

6:27 am - 7:24 pm

SJU

CLE

12h 57m

2 stops

$238American Airlines

Thu, Sep 10 - Tue, Sep 15

1:54 pm - 12:41 am

CLE

SJU

10h 47m

1 stop

7:10 am - 11:38 pm

SJU

CLE

16h 28m

1 stop

$241Frontier

Mon, Aug 10 - Thu, Aug 13

1:54 pm - 12:41 am

CLE

SJU

10h 47m

1 stop

6:45 am - 11:29 pm

SJU

CLE

16h 44m

1 stop

$243Frontier

Fri, Aug 14 - Tue, Aug 18

7:00 am - 8:38 pm

CLE

SJU

13h 38m

2 stops

4:55 pm - 11:44 pm

SJU

CLE

6h 49m

1 stop

$258United Airlines

Sat, Aug 15 - Fri, Aug 21

7:31 pm - 11:34 am

CLE

NAS

16h 03m

1 stop

2:18 pm - 10:21 pm

NAS

CLE

8h 03m

1 stop

$314American Airlines

Fri, Jul 10 - Wed, Jul 15

5:35 am - 2:01 pm

CLE

NAS

8h 26m

1 stop

3:26 pm - 12:49 am

NAS

CLE

9h 23m

1 stop

$322Delta

Fri, Jul 24 - Mon, Jul 27

7:50 am - 3:23 pm

CLE

SDQ

7h 33m

1 stop

4:44 pm - 11:54 pm

SDQ

CLE

7h 10m

1 stop

$376JetBlue

Thu, Aug 27 - Sun, Aug 30

7:50 am - 3:23 pm

CLE

SDQ

7h 33m

1 stop

4:44 pm - 11:54 pm

SDQ

CLE

7h 10m

1 stop

$384JetBlue

Mon, Aug 24 - Thu, Aug 27

7:00 am - 4:35 pm

CLE

MBJ

9h 35m

1 stop

6:00 pm - 12:35 am

MBJ

CLE

6h 35m

1 stop

$463Delta

Sun, Nov 15 - Sat, Nov 21

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American Airlines flights from Cleveland to Caribbean Islands

Our best American Airlines deals on Cleveland to Caribbean Islands flight tickets

American Airlines

Sep 10

CLE8:18 amCleveland Hopkins Intl

6h 49m

1 stop

SJU3:07 pmSan Juan Luis Munoz Marin Intl

Sep 15

SJU6:27 amSan Juan Luis Munoz Marin Intl

12h 57m

2 stops

CLE7:24 pmCleveland Hopkins Intl

$238

American Airlines

Jul 1

CLE7:07 amCleveland Hopkins Intl

15h 53m

1 stop

SJU11:00 pmSan Juan Luis Munoz Marin Intl

Sep 2

SJU7:03 amSan Juan Luis Munoz Marin Intl

15h 02m

1 stop

CLE10:05 pmCleveland Hopkins Intl

$302

American Airlines

Jun 27

CLE6:01 amCleveland Hopkins Intl

13h 55m

1 stop

NAS7:56 pmNassau Intl

Jul 1

NAS8:00 amNassau Intl

10h 33m

1 stop

CLE6:33 pmCleveland Hopkins Intl

$306

Frontier flights from Cleveland to Caribbean Islands

Our best Frontier deals on Cleveland to Caribbean Islands flight tickets

Frontier

Aug 10

CLE1:54 pmCleveland Hopkins Intl

10h 47m

1 stop

SJU12:41 amSan Juan Luis Munoz Marin Intl

Aug 13

SJU7:10 amSan Juan Luis Munoz Marin Intl

16h 28m

1 stop

CLE11:38 pmCleveland Hopkins Intl

$241

Frontier

Aug 14

CLE1:54 pmCleveland Hopkins Intl

10h 47m

1 stop

SJU12:41 amSan Juan Luis Munoz Marin Intl

Aug 18

SJU6:45 amSan Juan Luis Munoz Marin Intl

16h 44m

1 stop

CLE11:29 pmCleveland Hopkins Intl

$243

Frontier

Jul 21

CLE6:30 amCleveland Hopkins Intl

18h 11m

1 stop

SJU12:41 amSan Juan Luis Munoz Marin Intl

Jul 30

SJU6:00 amSan Juan Luis Munoz Marin Intl

16h 57m

1 stop

CLE10:57 pmCleveland Hopkins Intl

$246

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

Sat 9/12

5:30 am-2:44 pm

1 stop9h 14m

San Juan Luis Munoz Marin Intl

Sat 9/12

1:00 am-10:39 am

1 stop9h 39m

$233

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Thu 9/10

8:18 am-3:07 pm

1 stop6h 49m

San Juan Luis Munoz Marin Intl

Tue 9/15

6:27 am-7:24 pm

2 stops12h 57m

$238

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 8/10

1:54 pm-12:41 am

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Thu 8/13

7:10 am-11:38 pm

1 stop16h 28m

$241

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 8/14

1:54 pm-12:41 am

1 stop10h 47m

San Juan Luis Munoz Marin Intl

Tue 8/18

6:45 am-11:29 pm

1 stop16h 44m

$243

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 8/15

7:00 am-8:38 pm

2 stops13h 38m

San Juan Luis Munoz Marin Intl

Fri 8/21

4:55 pm-11:44 pm

1 stop6h 49m

$258

ClevelandNassau

CLE - NAS

CLENAS

Cleveland Hopkins Intl

Fri 7/10

7:31 pm-11:34 am

1 stop16h 03m

Nassau Intl

Wed 7/15

2:18 pm-10:21 pm

1 stop8h 03m

$314

ClevelandNassau

CLE - NAS

CLENAS

Cleveland Hopkins Intl

Fri 7/24

5:35 am-2:01 pm

1 stop8h 26m

Nassau Intl

Mon 7/27

3:26 pm-12:49 am

1 stop9h 23m

$322

Quickest round-trip

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

Thu 8/27

7:50 am-3:23 pm

1 stop7h 33m

Santo Domingo Las Americas

Sun 8/30

4:44 pm-11:54 pm

1 stop7h 10m

$376

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

Mon 8/24

7:50 am-3:23 pm

1 stop7h 33m

Santo Domingo Las Americas

Thu 8/27

4:44 pm-11:54 pm

1 stop7h 10m

$384

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Sun 11/15

7:00 am-4:35 pm

1 stop9h 35m

Montego Bay Sangster Intl

Sat 11/21

6:00 pm-12:35 am

1 stop6h 35m

$463

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 July is, on average, the cheapest month to fly to Caribbean Islands from Cleveland, with most prices found around $117. The month of November is another great option to travel to Caribbean Islands, with average flight prices from Cleveland averaging around $137.

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 Wednesday. Travelers who choose to depart for Caribbean Islands on a Wednesday will often find tickets for as low as $283. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $397. 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 morning. momondo users have found flights departing from Cleveland to Caribbean Islands in the morning for as low as $306. 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 evening because they tend to be around $451. 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 $354 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 $286 on momondo.

What cabin class options are available on Cleveland to Caribbean Islands flights?

There is only 1 cabin class available to choose from on Cleveland to Caribbean Islands flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

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 18m
Direct flights	Mon, Wed and Fri
Airports in Caribbean Islands	99 airports

The fastest flight from Cleveland to Caribbean Islands takes 4h 18m

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 June 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 A321neo, making up 17.84% of the total bookings. Other popular models include Airbus A320neo with 11.62%, Boeing 737-800 with 10.54%, and Boeing 737 MAX 8 with 10.48%.

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 $123	Free Cancellation	Rating 7.8 8,453 reviews	Search Delta flights
JetBlue	PriceFrom $160	Free Cancellation	Rating 7.1 3,011 reviews	Search JetBlue flights
Frontier	PriceFrom $181	Free Cancellation	Rating 5.6 2,864 reviews	Search Frontier flights
American Airlines	PriceFrom $225	Free Cancellation	Rating 7.1 11,768 reviews	Search American Airlines flights
United Airlines	PriceFrom $225	Free Cancellation	Rating 7.4 9,893 reviews	Search United Airlines flights
Southwest	PriceFrom $246	Free Cancellation	Rating 7.9 4,245 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.