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Cheap flights from Cleveland to Caribbean Islands from $100

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Cleveland to Caribbean Islands departing on 12/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Cleveland to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:29 pm - 2:53 am
CLE
-
SJU
7h 24m1 stop
Frontier Logo
7:05 am - 7:54 pm
SJU
-
CLE
13h 49m1 stop
$211Frontier
Sun, Feb 22 - Sat, Feb 28
Frontier Logo
6:00 pm - 3:31 pm
CLE
-
SJU
20h 31m1 stop
Frontier Logo
6:00 am - 10:37 pm
SJU
-
CLE
17h 37m1 stop
$212Frontier
Sat, Jan 24 - Sun, Feb 1
Frontier Logo
4:48 pm - 2:50 am
CLE
-
SJU
9h 02m1 stop
Frontier Logo
4:07 pm - 12:26 am
SJU
-
CLE
9h 19m1 stop
$215Frontier
Mon, Jan 5 - Fri, Jan 9
Spirit Airlines Logo
7:10 pm - 4:36 pm
CLE
-
PUJ
20h 26m1 stop
Spirit Airlines Logo
5:47 pm - 6:09 pm
PUJ
-
CLE
25h 22m1 stop
$303Spirit Airlines
Sat, Feb 21 - Wed, Feb 25
Spirit Airlines Logo
7:04 pm - 4:36 pm
CLE
-
PUJ
20h 32m1 stop
Spirit Airlines Logo
5:47 pm - 6:09 pm
PUJ
-
CLE
25h 22m1 stop
$321Spirit Airlines
Tue, Feb 17 - Mon, Feb 23
Delta Logo
7:38 pm - 12:55 pm
CLE
-
AUA
16h 17m1 stop
Delta Logo
4:40 pm - 11:53 am
AUA
-
CLE
20h 13m1 stop
$322Delta
Thu, Feb 12 - Sun, Feb 15
American Airlines Logo
7:47 pm - 2:42 pm
CLE
-
AUA
17h 55m2 stops
American Airlines Logo
5:59 pm - 11:55 am
AUA
-
CLE
18h 56m2 stops
$326American Airlines
Sun, Jan 18 - Sat, Jan 24
American Airlines Logo
4:13 pm - 1:59 pm
CLE
-
AUA
20h 46m1 stop
American Airlines Logo
5:59 pm - 10:30 am
AUA
-
CLE
17h 31m1 stop
$328American Airlines
Sun, Jan 18 - Sat, Jan 24
Delta Logo
6:00 am - 3:20 pm
CLE
-
AUA
8h 20m1 stop
Delta Logo
2:10 pm - 8:33 pm
AUA
-
CLE
7h 23m1 stop
$346Delta
Wed, Feb 11 - Wed, Feb 18
United Airlines Logo
6:25 am - 1:17 pm
CLE
-
PLS
6h 52m1 stop
United Airlines Logo
5:06 pm - 9:50 am
PLS
-
CLE
16h 44m1 stop
$384United Airlines
Sat, Feb 21 - Tue, Feb 24

Frontier flights from Cleveland to Caribbean Islands

Our best Frontier deals on Cleveland to Caribbean Islands flight tickets
Frontier
Feb 22
CLE6:29 pmCleveland Hopkins Intl
7h 24m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
Feb 28
SJU7:05 amSan Juan Luis Munoz Marin Intl
13h 49m
1 stop
CLE7:54 pmCleveland Hopkins Intl
$211
Find similar
Frontier
Jan 24
CLE6:00 pmCleveland Hopkins Intl
20h 31m
1 stop
SJU3:31 pmSan Juan Luis Munoz Marin Intl
Feb 1
SJU6:00 amSan Juan Luis Munoz Marin Intl
17h 37m
1 stop
CLE10:37 pmCleveland Hopkins Intl
$212
Find similar
Frontier
Jan 5
CLE4:48 pmCleveland Hopkins Intl
9h 02m
1 stop
SJU2:50 amSan Juan Luis Munoz Marin Intl
Jan 9
SJU4:07 pmSan Juan Luis Munoz Marin Intl
9h 19m
1 stop
CLE12:26 amCleveland Hopkins Intl
$215
Find similar

American Airlines flights from Cleveland to Caribbean Islands

Our best American Airlines deals on Cleveland to Caribbean Islands flight tickets
American Airlines
Feb 24
CLE6:00 amCleveland Hopkins Intl
8h 46m
2 stops
SJU3:46 pmSan Juan Luis Munoz Marin Intl
Mar 4
SJU7:00 amSan Juan Luis Munoz Marin Intl
9h 34m
2 stops
CLE3:34 pmCleveland Hopkins Intl
$225
Find similar
American Airlines
Jan 2
CLE6:00 amCleveland Hopkins Intl
9h 17m
2 stops
SJU4:17 pmSan Juan Luis Munoz Marin Intl
Jan 12
SJU6:00 amSan Juan Luis Munoz Marin Intl
12h 36m
1 stop
CLE5:36 pmCleveland Hopkins Intl
$317
Find similar
American Airlines
Jan 18
CLE4:27 pmCleveland Hopkins Intl
20h 33m
2 stops
AUA2:00 pmOranjestad Reina Beatrix
Jan 24
AUA3:46 pmOranjestad Reina Beatrix
9h 08m
1 stop
CLE11:54 pmCleveland Hopkins Intl
$326
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Cleveland to Caribbean Islands 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, momondo users made 832,500 searches. Data last updated December 23, 2025.
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

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 2/22

6:29 pm-2:53 am

1 stop7h 24m

San Juan Luis Munoz Marin Intl

Sat 2/28

7:05 am-7:54 pm

1 stop13h 49m

$211

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 1/24

6:00 pm-3:31 pm

1 stop20h 31m

San Juan Luis Munoz Marin Intl

Sun 2/1

6:00 am-10:37 pm

1 stop17h 37m

$212

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 1/5

4:48 pm-2:50 am

1 stop9h 02m

San Juan Luis Munoz Marin Intl

Fri 1/9

4:07 pm-12:26 am

1 stop9h 19m

$215

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

Sat 2/21

7:10 pm-4:36 pm

1 stop20h 26m

Punta Cana

Wed 2/25

5:47 pm-6:09 pm

1 stop25h 22m

$303

ClevelandPunta Cana

CLE - PUJ

CLEPUJ

Cleveland Hopkins Intl

Tue 2/17

7:04 pm-4:36 pm

1 stop20h 32m

Punta Cana

Mon 2/23

5:47 pm-6:09 pm

1 stop25h 22m

$321

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Thu 2/12

7:38 pm-12:55 pm

1 stop16h 17m

Oranjestad Reina Beatrix

Sun 2/15

4:40 pm-11:53 am

1 stop20h 13m

$322

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Sun 1/18

7:47 pm-2:42 pm

2 stops17h 55m

Oranjestad Reina Beatrix

Sat 1/24

5:59 pm-11:55 am

2 stops18h 56m

$326

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Sun 1/18

4:13 pm-1:59 pm

1 stop20h 46m

Oranjestad Reina Beatrix

Sat 1/24

5:59 pm-10:30 am

1 stop17h 31m

$328

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Wed 2/11

6:00 am-3:20 pm

1 stop8h 20m

Oranjestad Reina Beatrix

Wed 2/18

2:10 pm-8:33 pm

1 stop7h 23m

$346

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Sat 2/21

6:25 am-1:17 pm

1 stop6h 52m

Providenciales

Tue 2/24

5:06 pm-9:50 am

1 stop16h 44m

$384

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Caribbean Islands from

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

What is the cheapest month to fly to Caribbean Islands?

The month of May is, on average, the cheapest month to fly to Caribbean Islands from Cleveland, with most prices found around $262. The month of June is another great option to travel to Caribbean Islands, with average flight prices from Cleveland averaging around $274.

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 $225. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $292. 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 $256. 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 at noon because they tend to be around $348. 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 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 $316 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 $267 on momondo.

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

There is only 1 cabin class available to choose from on Cleveland Hopkins Intl 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 10m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Cleveland to Caribbean Islands takes 4h 10m
Direct flights go from Cleveland to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Cleveland there are direct flights to Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU).
Search flight deals

  • 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?

  • 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?

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
Spirit AirlinesPriceFrom $118Free CancellationRating
6.3
8,194 reviews
Search Spirit Airlines flights
FrontierPriceFrom $153Free CancellationRating
5.8
3,074 reviews
Search Frontier flights
DeltaPriceFrom $163Free CancellationRating
7.9
8,015 reviews
Search Delta flights
American AirlinesPriceFrom $211Free CancellationRating
7.2
11,050 reviews
Search American Airlines flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,106 reviews
Search United Airlines flights
SouthwestPriceFrom $264Free CancellationRating
8.0
4,255 reviews
Search Southwest flights
JetBluePriceFrom $278Free CancellationRating
7.2
2,898 reviews
Search JetBlue 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.

An easier way to manage your Caribbean Islands trip

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