Cheap flights from Cleveland to Caribbean from $96

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 4/18. 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
1 adult, Economy, 0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:13 am - 5:59 pm
CLE
-
SJU
6h 46m
1 stop
Frontier Logo
3:33 pm - 11:11 pm
SJU
-
CLE
7h 38m
1 stop
$212Frontier
Fri, May 1 - Tue, May 5
Frontier Logo
10:00 pm - 10:48 pm
CLE
-
SJU
24h 48m
1 stop
Frontier Logo
6:30 am - 12:31 am
SJU
-
CLE
18h 01m
1 stop
$213Frontier
Fri, Apr 17 - Sun, Apr 26
Frontier Logo
7:38 pm - 12:23 pm
CLE
-
SJU
16h 45m
1 stop
Frontier Logo
3:19 pm - 11:40 pm
SJU
-
CLE
8h 21m
1 stop
$214Frontier
Wed, Apr 15 - Tue, Apr 21
Delta Logo
5:50 am - 2:48 pm
CLE
-
STT
8h 58m
1 stop
Delta Logo
3:59 pm - 11:46 pm
STT
-
CLE
7h 47m
1 stop
$270Delta
Mon, May 4 - Wed, May 6
American Airlines Logo
6:04 am - 4:15 pm
CLE
-
STT
10h 11m
1 stop
American Airlines Logo
11:27 am - 12:26 am
STT
-
CLE
12h 59m
2 stops
$275American Airlines
Wed, Apr 22 - Wed, Apr 29
United Airlines Logo
6:00 am - 12:20 pm
CLE
-
STT
6h 20m
1 stop
United Airlines Logo
1:22 pm - 10:38 pm
STT
-
CLE
9h 16m
1 stop
$290United Airlines
Fri, Apr 10 - Thu, Apr 16
United Airlines Logo
6:00 am - 3:10 pm
CLE
-
MBJ
10h 10m
1 stop
United Airlines Logo
4:12 pm - 11:59 pm
MBJ
-
CLE
6h 47m
1 stop
$352United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
6:49 pm - 11:35 am
CLE
-
STT
16h 46m
2 stops
American Airlines Logo
11:27 am - 11:36 pm
STT
-
CLE
12h 09m
1 stop
$358American Airlines
Fri, Apr 24 - Mon, Apr 27
JetBlue Logo
6:00 am - 12:54 pm
CLE
-
ANU
6h 54m
1 stop
JetBlue Logo
2:00 pm - 11:50 pm
ANU
-
CLE
9h 50m
1 stop
$567JetBlue
Sat, Apr 18 - Sat, Apr 25
JetBlue Logo
6:00 am - 12:54 pm
CLE
-
ANU
6h 54m
1 stop
JetBlue Logo
2:00 pm - 11:50 pm
ANU
-
CLE
9h 50m
1 stop
$569JetBlue
Sat, Apr 18 - Sat, Apr 25

Frontier flights from Cleveland to Caribbean

Our best Frontier deals on Cleveland to Caribbean flight tickets
Frontier
May 1
CLE11:13 amCleveland Hopkins Intl
6h 46m
1 stop
SJU5:59 pmSan Juan Luis Munoz Marin Intl
May 5
SJU3:33 pmSan Juan Luis Munoz Marin Intl
7h 38m
1 stop
CLE11:11 pmCleveland Hopkins Intl
$212
Frontier
Apr 17
CLE10:00 pmCleveland Hopkins Intl
24h 48m
1 stop
SJU10:48 pmSan Juan Luis Munoz Marin Intl
Apr 26
SJU6:30 amSan Juan Luis Munoz Marin Intl
18h 01m
1 stop
CLE12:31 amCleveland Hopkins Intl
$213
Frontier
Apr 15
CLE7:38 pmCleveland Hopkins Intl
16h 45m
1 stop
SJU12:23 pmSan Juan Luis Munoz Marin Intl
Apr 21
SJU3:19 pmSan Juan Luis Munoz Marin Intl
8h 21m
1 stop
CLE11:40 pmCleveland Hopkins Intl
$214

American Airlines flights from Cleveland to Caribbean

Our best American Airlines deals on Cleveland to Caribbean flight tickets
American Airlines
Apr 22
CLE6:04 amCleveland Hopkins Intl
10h 11m
1 stop
STT4:15 pmSaint Thomas Island Cyril E King
Apr 29
STT11:27 amSaint Thomas Island Cyril E King
12h 59m
2 stops
CLE12:26 amCleveland Hopkins Intl
$275
American Airlines
Mar 25
CLE6:22 pmCleveland Hopkins Intl
16h 34m
1 stop
SJU10:56 amSan Juan Luis Munoz Marin Intl
Apr 1
SJU7:11 amSan Juan Luis Munoz Marin Intl
16h 47m
1 stop
CLE11:58 pmCleveland Hopkins Intl
$341
American Airlines
May 9
CLE8:11 amCleveland Hopkins Intl
8h 26m
2 stops
MBJ3:37 pmMontego Bay Sangster Intl
May 12
MBJ4:37 pmMontego Bay Sangster Intl
19h 11m
2 stops
CLE12:48 pmCleveland Hopkins Intl
$357

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 March 23, 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
Quickest round-trip

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 5/1

11:13 am-5:59 pm

1 stop6h 46m

San Juan Luis Munoz Marin Intl

Tue 5/5

3:33 pm-11:11 pm

1 stop7h 38m

$212

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Fri 4/17

10:00 pm-10:48 pm

1 stop24h 48m

San Juan Luis Munoz Marin Intl

Sun 4/26

6:30 am-12:31 am

1 stop18h 01m

$213

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 4/15

7:38 pm-12:23 pm

1 stop16h 45m

San Juan Luis Munoz Marin Intl

Tue 4/21

3:19 pm-11:40 pm

1 stop8h 21m

$214

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Mon 5/4

5:50 am-2:48 pm

1 stop8h 58m

Saint Thomas Island Cyril E King

Wed 5/6

3:59 pm-11:46 pm

1 stop7h 47m

$270

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Wed 4/22

6:04 am-4:15 pm

1 stop10h 11m

Saint Thomas Island Cyril E King

Wed 4/29

11:27 am-12:26 am

2 stops12h 59m

$275

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Fri 4/10

6:00 am-12:20 pm

1 stop6h 20m

Saint Thomas Island Cyril E King

Thu 4/16

1:22 pm-10:38 pm

1 stop9h 16m

$290

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Sat 4/18

6:00 am-3:10 pm

1 stop10h 10m

Montego Bay Sangster Intl

Sat 4/25

4:12 pm-11:59 pm

1 stop6h 47m

$352

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Fri 4/24

6:49 pm-11:35 am

2 stops16h 46m

Saint Thomas Island Cyril E King

Mon 4/27

11:27 am-11:36 pm

1 stop12h 09m

$358

ClevelandSt. John's

CLE - ANU

CLEANU

Cleveland Hopkins Intl

Sat 4/18

6:00 am-12:54 pm

1 stop6h 54m

St. John's V.C. Bird Intl

Sat 4/25

2:00 pm-11:50 pm

1 stop9h 50m

$567

ClevelandSt. John's

CLE - ANU

CLEANU

Cleveland Hopkins Intl

Sat 4/18

6:00 am-12:54 pm

1 stop6h 54m

St. John's V.C. Bird Intl

Sat 4/25

2:00 pm-11:50 pm

1 stop9h 50m

$569

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 $246. If you don’t want to visit Caribbean in May, then you should wait until April 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 $216. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $320. 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 evening is the cheapest time of day to fly from Cleveland to Caribbean when you can find flight prices for as low as $250. Flying to Caribbean in the evening 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 $323 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 $267 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

$619

Fastest flight time

4h 10m

Direct flights

Mon, Wed and Fri

Airports in Caribbean

195 airports
The best flight deal from Cleveland to Caribbean found on momondo in the last 72 hours is $619
The fastest flight from Cleveland to Caribbean takes 4h 10m
Direct flights go from Cleveland to Caribbean on Monday, Wednesday and Friday. There are no airlines offering direct flights.
There are 195 airports in Caribbean. From Cleveland there are direct flights to Punta Cana (PUJ).
  • 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
DeltaPriceFrom $102Free CancellationRating
7.9
8,318 reviews
Search Delta flights
Spirit AirlinesPriceFrom $137Free CancellationRating
6.3
8,538 reviews
Search Spirit Airlines flights
JetBluePriceFrom $160Free CancellationRating
7.2
2,908 reviews
Search JetBlue flights
FrontierPriceFrom $160Free CancellationRating
5.7
3,020 reviews
Search Frontier flights
American AirlinesPriceFrom $220Free CancellationRating
7.1
11,486 reviews
Search American Airlines flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,462 reviews
Search United Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,324 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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1 adult
Wed 4/22
Wed 4/29

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