Cheap flights from Cleveland to Caribbean from $142

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 6/8. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
7:24 pm - 2:33 pm
CLE
-
SJU
43h 09m
2 stops
Frontier Logo
5:15 pm - 12:43 am
SJU
-
CLE
7h 28m
1 stop
$289Frontier
Sat, Jun 6 - Wed, Jun 10
Frontier Logo
2:29 pm - 11:29 pm
CLE
-
SJU
9h 00m
1 stop
Frontier Logo
6:00 am - 1:24 pm
SJU
-
CLE
7h 24m
1 stop
$291Frontier
Tue, Aug 18 - Wed, Aug 19
American Airlines Logo
6:30 am - 2:50 pm
CLE
-
MBJ
8h 20m
1 stop
American Airlines Logo
1:55 pm - 12:43 am
MBJ
-
CLE
10h 48m
1 stop
$372American Airlines
Sun, Nov 15 - Sat, Nov 21
United Airlines Logo
6:00 am - 12:40 pm
CLE
-
AUA
6h 40m
1 stop
United Airlines Logo
4:30 pm - 11:44 pm
AUA
-
CLE
7h 14m
1 stop
$375United Airlines
Wed, Jun 10 - Wed, Jun 17
American Airlines Logo
5:31 am - 1:17 pm
CLE
-
MBJ
8h 46m
1 stop
American Airlines Logo
5:13 pm - 11:47 am
MBJ
-
CLE
17h 34m
2 stops
$377American Airlines
Thu, Aug 13 - Mon, Aug 17
United Airlines Logo
6:52 pm - 1:30 pm
CLE
-
MBJ
19h 38m
1 stop
United Airlines Logo
1:48 pm - 11:58 pm
MBJ
-
CLE
9h 10m
1 stop
$380United Airlines
Fri, Oct 23 - Mon, Oct 26
Delta Logo
8:05 am - 3:00 pm
CLE
-
STT
6h 55m
1 stop
Delta Logo
3:02 pm - 12:36 am
STT
-
CLE
9h 34m
1 stop
$434Delta
Sat, Sep 5 - Tue, Sep 8
Delta Logo
7:00 am - 1:44 pm
CLE
-
STT
6h 44m
1 stop
Delta Logo
2:54 pm - 9:54 pm
STT
-
CLE
7h 00m
1 stop
$470Delta
Sat, Sep 26 - Sat, Oct 3
JetBlue Logo
6:25 am - 1:00 pm
CLE
-
PLS
6h 35m
1 stop
JetBlue Logo
2:25 pm - 11:59 pm
PLS
-
CLE
9h 34m
1 stop
$562JetBlue
Tue, Jul 28 - Thu, Jul 30
JetBlue Logo
6:25 am - 1:00 pm
CLE
-
PLS
6h 35m
1 stop
JetBlue Logo
2:25 pm - 11:59 pm
PLS
-
CLE
9h 34m
1 stop
$567JetBlue
Sun, Jul 19 - Thu, Jul 30

Frontier flights from Cleveland to Caribbean

Our best Frontier deals on Cleveland to Caribbean flight tickets
Frontier
Jun 6
CLE7:24 pmCleveland Hopkins Intl
43h 09m
2 stops
SJU2:33 pmSan Juan Luis Munoz Marin Intl
Jun 10
SJU5:15 pmSan Juan Luis Munoz Marin Intl
7h 28m
1 stop
CLE12:43 amCleveland Hopkins Intl
$289
Frontier
Aug 18
CLE2:29 pmCleveland Hopkins Intl
9h 00m
1 stop
SJU11:29 pmSan Juan Luis Munoz Marin Intl
Aug 19
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 24m
1 stop
CLE1:24 pmCleveland Hopkins Intl
$291
Frontier
Jul 4
CLE2:05 pmCleveland Hopkins Intl
10h 32m
1 stop
SJU12:37 amSan Juan Luis Munoz Marin Intl
Jul 7
SJU7:30 amSan Juan Luis Munoz Marin Intl
16h 08m
1 stop
CLE11:38 pmCleveland Hopkins Intl
$292

American Airlines flights from Cleveland to Caribbean

Our best American Airlines deals on Cleveland to Caribbean flight tickets
American Airlines
Jun 6
CLE3:54 pmCleveland Hopkins Intl
6h 51m
1 stop
SJU10:45 pmSan Juan Luis Munoz Marin Intl
Jun 10
SJU6:21 amSan Juan Luis Munoz Marin Intl
17h 18m
1 stop
CLE11:39 pmCleveland Hopkins Intl
$336
American Airlines
Jun 1
CLE7:08 amCleveland Hopkins Intl
15h 53m
1 stop
SJU11:01 pmSan Juan Luis Munoz Marin Intl
Jun 4
SJU7:00 amSan Juan Luis Munoz Marin Intl
17h 23m
1 stop
CLE12:23 amCleveland Hopkins Intl
$346
American Airlines
Nov 15
CLE6:30 amCleveland Hopkins Intl
8h 20m
1 stop
MBJ2:50 pmMontego Bay Sangster Intl
Nov 21
MBJ1:55 pmMontego Bay Sangster Intl
10h 48m
1 stop
CLE12:43 amCleveland Hopkins Intl
$372

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 May 20, 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

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 6/6

7:24 pm-2:33 pm

2 stops43h 09m

San Juan Luis Munoz Marin Intl

Wed 6/10

5:15 pm-12:43 am

1 stop7h 28m

$289

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Tue 8/18

2:29 pm-11:29 pm

1 stop9h 00m

San Juan Luis Munoz Marin Intl

Wed 8/19

6:00 am-1:24 pm

1 stop7h 24m

$291

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Sun 11/15

6:30 am-2:50 pm

1 stop8h 20m

Montego Bay Sangster Intl

Sat 11/21

1:55 pm-12:43 am

1 stop10h 48m

$372

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

Wed 6/10

6:00 am-12:40 pm

1 stop6h 40m

Oranjestad Reina Beatrix

Wed 6/17

4:30 pm-11:44 pm

1 stop7h 14m

$375

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Thu 8/13

5:31 am-1:17 pm

1 stop8h 46m

Montego Bay Sangster Intl

Mon 8/17

5:13 pm-11:47 am

2 stops17h 34m

$377

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

Fri 10/23

6:52 pm-1:30 pm

1 stop19h 38m

Montego Bay Sangster Intl

Mon 10/26

1:48 pm-11:58 pm

1 stop9h 10m

$380

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sat 9/5

8:05 am-3:00 pm

1 stop6h 55m

Saint Thomas Island Cyril E King

Tue 9/8

3:02 pm-12:36 am

1 stop9h 34m

$434
Quickest round-trip

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sat 9/26

7:00 am-1:44 pm

1 stop6h 44m

Saint Thomas Island Cyril E King

Sat 10/3

2:54 pm-9:54 pm

1 stop7h 00m

$470

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Tue 7/28

6:25 am-1:00 pm

1 stop6h 35m

Providenciales

Thu 7/30

2:25 pm-11:59 pm

1 stop9h 34m

$562

ClevelandProvidenciales

CLE - PLS

CLEPLS

Cleveland Hopkins Intl

Sun 7/19

6:25 am-1:00 pm

1 stop6h 35m

Providenciales

Thu 7/30

2:25 pm-11:59 pm

1 stop9h 34m

$567

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, September 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 $138. If you don’t want to visit Caribbean in September, then you should wait until March to fly from Cleveland, when ticket prices are also cheap, with an average price of $416.

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 $259. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $375. 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 $266. Flying to Caribbean in the afternoon is an ideal time because this is during off-peak travel hours. Flights in the evening are often more expensive with an average ticket price of $328.

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 from Cleveland 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 $337 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 $270 on momondo.

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

There is only 1 cabin class available to choose from on Cleveland 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

$559

Fastest flight time

4h 14m

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 $559
The fastest flight from Cleveland to Caribbean takes 4h 14m
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).

Frequently asked questions about flying from Cleveland to Caribbean

  • 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
8,452 reviews
Search Delta flights
JetBluePriceFrom $160Free CancellationRating
7.2
2,982 reviews
Search JetBlue flights
FrontierPriceFrom $172Free CancellationRating
5.6
2,945 reviews
Search Frontier flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,738 reviews
Search United Airlines flights
American AirlinesPriceFrom $225Free CancellationRating
7.1
11,643 reviews
Search American Airlines flights
SouthwestPriceFrom $246Free CancellationRating
7.9
4,284 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
Fri 6/19
Fri 6/26

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