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Cheap flights from Cleveland to Caribbean from $95

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 departing on 4/7. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Cleveland to Caribbean

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
3:13 pm - 6:58 pm
CLE
-
SJU
26h 45m
1 stop
Multiple Airlines Logo
5:25 pm - 7:56 am
SJU
-
CLE
15h 31m
1 stop
$194Multiple Airlines
Mon, Mar 2 - Wed, Mar 4
Multiple Airlines Logo
2:40 pm - 6:58 pm
CLE
-
SJU
27h 18m
2 stops
Multiple Airlines Logo
11:44 am - 12:26 am
SJU
-
CLE
13h 42m
1 stop
$195Multiple Airlines
Mon, Feb 23 - Fri, Mar 6
Multiple Airlines Logo
2:40 pm - 6:58 pm
CLE
-
SJU
27h 18m
2 stops
Multiple Airlines Logo
11:52 am - 9:37 pm
SJU
-
CLE
10h 45m
1 stop
$196Multiple Airlines
Mon, Mar 2 - Thu, Mar 5
Frontier Logo
4:47 pm - 12:43 am
CLE
-
SJU
6h 56m
1 stop
Frontier Logo
4:11 pm - 10:55 pm
SJU
-
CLE
7h 44m
1 stop
$197Frontier
Tue, Feb 24 - Thu, Mar 5
Frontier Logo
7:18 pm - 12:39 pm
CLE
-
SJU
16h 21m
1 stop
Frontier Logo
3:53 am - 3:34 pm
SJU
-
CLE
12h 41m
1 stop
$199Frontier
Sun, Feb 22 - Tue, Feb 24
Spirit Airlines Logo
7:04 pm - 3:40 pm
CLE
-
STX
19h 36m
1 stop
Spirit Airlines Logo
4:37 pm - 6:09 pm
STX
-
CLE
26h 32m
1 stop
$264Spirit Airlines
Thu, Feb 26 - Mon, Mar 2
Spirit Airlines Logo
5:35 pm - 11:02 am
CLE
-
MBJ
18h 27m
1 stop
Spirit Airlines Logo
12:00 pm - 4:40 pm
MBJ
-
CLE
27h 40m
1 stop
$327Spirit Airlines
Tue, Apr 21 - Mon, Apr 27
Delta Logo
6:00 am - 3:05 pm
CLE
-
UVF
8h 05m
1 stop
Delta Logo
3:18 pm - 12:29 am
UVF
-
CLE
9h 11m
1 stop
$434Delta
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:00 am - 3:58 pm
CLE
-
UVF
8h 58m
1 stop
American Airlines Logo
2:48 pm - 9:01 am
UVF
-
CLE
18h 13m
2 stops
$439American Airlines
Wed, Mar 4 - Wed, Mar 11
American Airlines Logo
6:00 am - 1:48 pm
CLE
-
UVF
7h 48m
1 stop
American Airlines Logo
3:58 pm - 5:42 pm
UVF
-
CLE
25h 44m
1 stop
$444American Airlines
Tue, Mar 24 - Mon, Mar 30

Frontier flights from Cleveland to Caribbean

Our best Frontier deals on Cleveland to Caribbean flight tickets
Frontier
Feb 24
CLE4:47 pmCleveland Hopkins Intl
6h 56m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
Mar 5
SJU4:11 pmSan Juan Luis Munoz Marin Intl
7h 44m
1 stop
CLE10:55 pmCleveland Hopkins Intl
$197
Frontier
Feb 22
CLE7:18 pmCleveland Hopkins Intl
16h 21m
1 stop
SJU12:39 pmSan Juan Luis Munoz Marin Intl
Feb 24
SJU3:53 amSan Juan Luis Munoz Marin Intl
12h 41m
1 stop
CLE3:34 pmCleveland Hopkins Intl
$199
Frontier
Apr 26
CLE6:15 amCleveland Hopkins Intl
30h 18m
1 stop
SJU12:33 pmSan Juan Luis Munoz Marin Intl
May 4
SJU3:42 pmSan Juan Luis Munoz Marin Intl
9h 14m
1 stop
CLE12:56 amCleveland Hopkins Intl
$200

American Airlines flights from Cleveland to Caribbean

Our best American Airlines deals on Cleveland to Caribbean flight tickets
American Airlines
Feb 16
CLE3:29 pmCleveland Hopkins Intl
12h 55m
1 stop
SJU5:24 amSan Juan Luis Munoz Marin Intl
Feb 20
SJU6:00 amSan Juan Luis Munoz Marin Intl
16h 37m
1 stop
CLE9:37 pmCleveland Hopkins Intl
$271
American Airlines
Feb 28
CLE6:55 pmCleveland Hopkins Intl
16h 38m
1 stop
AUA12:33 pmOranjestad Reina Beatrix
Mar 7
AUA4:50 pmOranjestad Reina Beatrix
16h 19m
2 stops
CLE8:09 amCleveland Hopkins Intl
$348
American Airlines
Mar 22
CLE6:22 pmCleveland Hopkins Intl
21h 21m
1 stop
AUA3:43 pmOranjestad Reina Beatrix
Mar 26
AUA5:13 pmOranjestad Reina Beatrix
15h 48m
1 stop
CLE9:01 amCleveland Hopkins Intl
$352

momondo 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, momondo users made 832,500 searches. Data last updated February 6, 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

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 3/2

3:13 pm-6:58 pm

1 stop26h 45m

San Juan Luis Munoz Marin Intl

Wed 3/4

5:25 pm-7:56 am

1 stop15h 31m

$194

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 2/23

2:40 pm-6:58 pm

2 stops27h 18m

San Juan Luis Munoz Marin Intl

Fri 3/6

11:44 am-12:26 am

1 stop13h 42m

$195

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 3/2

2:40 pm-6:58 pm

2 stops27h 18m

San Juan Luis Munoz Marin Intl

Thu 3/5

11:52 am-9:37 pm

1 stop10h 45m

$196

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 2/24

4:47 pm-12:43 am

1 stop6h 56m

San Juan Luis Munoz Marin Intl

Thu 3/5

4:11 pm-10:55 pm

1 stop7h 44m

$197

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 2/22

7:18 pm-12:39 pm

1 stop16h 21m

San Juan Luis Munoz Marin Intl

Tue 2/24

3:53 am-3:34 pm

1 stop12h 41m

$199

ClevelandChristiansted

CLE - STX

CLESTX

Cleveland Hopkins Intl

Thu 2/26

7:04 pm-3:40 pm

1 stop19h 36m

Christiansted Henry Rohlsen

Mon 3/2

4:37 pm-6:09 pm

1 stop26h 32m

$264

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Tue 4/21

5:35 pm-11:02 am

1 stop18h 27m

Montego Bay Sangster Intl

Mon 4/27

12:00 pm-4:40 pm

1 stop27h 40m

$327

ClevelandCastries

CLE - UVF

CLEUVF

Cleveland Hopkins Intl

Wed 3/4

6:00 am-3:05 pm

1 stop8h 05m

Castries Hewanorra

Wed 3/11

3:18 pm-12:29 am

1 stop9h 11m

$434

ClevelandCastries

CLE - UVF

CLEUVF

Cleveland Hopkins Intl

Wed 3/4

6:00 am-3:58 pm

1 stop8h 58m

Castries Hewanorra

Wed 3/11

2:48 pm-9:01 am

2 stops18h 13m

$439

ClevelandCastries

CLE - UVF

CLEUVF

Cleveland Hopkins Intl

Tue 3/24

6:00 am-1:48 pm

1 stop7h 48m

Castries Hewanorra

Mon 3/30

3:58 pm-5:42 pm

1 stop25h 44m

$444

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Cleveland to Caribbean

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?

In general, May is the cheapest month to fly from Cleveland to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $258. If you don’t want to visit Caribbean in May, then you should wait until June to fly from Cleveland, when ticket prices are also cheap, with an average price of $278.

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

The cheapest day to depart from Cleveland to Caribbean is on a Tuesday when prices can be found for as low as $221. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $291. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

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

In the afternoon is the cheapest time of day to fly from Cleveland to Caribbean when you can find flight prices for as low as $253. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the morning are often more expensive with an average ticket price of $283.

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

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

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

You are more likely to see cheaper flights to Caribbean from Cleveland when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $317 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Cleveland for as low as $260 on momondo.

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

There is only 1 cabin class available to choose from on Cleveland Hopkins Intl to Caribbean 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 flights?

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

Cheap Cleveland to Caribbean flight deals and tips

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

Best Price Found

$229

Fastest flight time

4h 10m

Direct flights

Mon, Wed and Fri

Airports in Caribbean

195 airports
The best one-way flight to Caribbean from Cleveland in the past 72 hours is $229. The best round-trip flight deal from Cleveland to Caribbean found on momondo in the last 72 hours is $486.
The fastest flight from Cleveland to Caribbean takes 4h 10m
Direct flights go from Cleveland to Caribbean on Monday, Wednesday and Friday. The only airline offering direct flights is Frontier.
There are 195 airports in Caribbean. From Cleveland there are direct flights to Punta Cana (PUJ).
Search flight deals

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

    Prices for flights from Cleveland Hopkins Intl Airport to Caribbean were last updated today.

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Cleveland Hopkins Intl Airport to Caribbean.

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

    The required travel and health documents for your Caribbean 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. 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?

Best airlines flying from Cleveland to Caribbean

Compare and see reviews for airlines that fly from Cleveland to Caribbean with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,421 reviews
Search Spirit Airlines flights
DeltaPriceFrom $106Free CancellationRating
7.9
8,159 reviews
Search Delta flights
JetBluePriceFrom $154Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
FrontierPriceFrom $154Free CancellationRating
5.7
3,054 reviews
Search Frontier flights
American AirlinesPriceFrom $217Free CancellationRating
7.2
11,247 reviews
Search American Airlines flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,244 reviews
Search United Airlines flights
SouthwestPriceFrom $245Free CancellationRating
8.0
4,279 reviews
Search Southwest flights

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Cleveland to Caribbean. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Caribbean from Cleveland which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Cleveland to Caribbean.

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

Yes. momondo can track prices for Cleveland to Caribbean flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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Find better results for your trip to Caribbean

Popular cities in Caribbean

Popular flights according to clicks in the last 7 days on momondo
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