Cheap flights from Cleveland to Caribbean Islands 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 Islands departing on 3/2. 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
6:29 pm - 2:53 am
CLE
-
SJU
7h 24m
1 stop
Frontier Logo
3:18 pm - 11:14 pm
SJU
-
CLE
7h 56m
1 stop
$194Frontier
ma., mar. 2 - lø., mai 2
Frontier Logo
4:31 pm - 2:01 am
CLE
-
SJU
9h 30m
1 stop
Frontier Logo
6:00 am - 1:14 pm
SJU
-
CLE
7h 14m
1 stop
$196Frontier
fr., apr. 10 - fr., apr. 17
Frontier Logo
4:47 pm - 12:43 am
CLE
-
SJU
6h 56m
1 stop
Frontier Logo
6:39 pm - 7:31 pm
SJU
-
CLE
24h 52m
1 stop
$199Frontier
on., mar. 4 - on., mar. 11
Delta Logo
5:50 am - 2:48 pm
CLE
-
STT
8h 58m
1 stop
Delta Logo
3:05 pm - 12:34 am
STT
-
CLE
9h 29m
1 stop
$270Delta
on., apr. 22 - fr., apr. 24
Spirit Airlines Logo
6:31 pm - 1:38 am
CLE
-
SDQ
7h 07m
1 stop
Spirit Airlines Logo
2:52 am - 5:13 pm
SDQ
-
CLE
14h 21m
1 stop
$302Spirit Airlines
ti., mar. 17 - ma., mar. 23
Spirit Airlines Logo
6:31 pm - 2:35 pm
CLE
-
AUA
20h 04m
1 stop
Spirit Airlines Logo
3:41 pm - 4:30 pm
AUA
-
CLE
24h 49m
1 stop
$311Spirit Airlines
on., apr. 8 - to., apr. 16
American Airlines Logo
6:00 am - 1:25 pm
CLE
-
MBJ
8h 25m
1 stop
American Airlines Logo
1:15 pm - 12:05 am
MBJ
-
CLE
9h 50m
1 stop
$312American Airlines
ma., apr. 13 - lø., apr. 18
American Airlines Logo
7:40 pm - 11:24 am
CLE
-
MBJ
16h 44m
2 stops
American Airlines Logo
4:37 pm - 12:48 pm
MBJ
-
CLE
19h 11m
2 stops
$317American Airlines
lø., mai 9 - ti., mai 12
United Airlines Logo
6:00 am - 12:50 pm
CLE
-
AUA
6h 50m
1 stop
United Airlines Logo
4:30 pm - 9:52 am
AUA
-
CLE
17h 22m
1 stop
$353United Airlines
ti., mar. 24 - ma., mar. 30
Delta Logo
6:00 am - 1:58 pm
CLE
-
UVF
7h 58m
1 stop
Delta Logo
3:18 pm - 12:29 am
UVF
-
CLE
9h 11m
1 stop
$464Delta
on., mar. 18 - on., mar. 25

Frontier flights from Cleveland to Caribbean Islands

Our best Frontier deals on Cleveland to Caribbean Islands flight tickets
Frontier
Mar 2
CLE6:29 pmCleveland Hopkins Intl
7h 24m
1 stop
SJU2:53 amSan Juan Luis Munoz Marin Intl
May 2
SJU3:18 pmSan Juan Luis Munoz Marin Intl
7h 56m
1 stop
CLE11:14 pmCleveland Hopkins Intl
$194
Frontier
Apr 10
CLE4:31 pmCleveland Hopkins Intl
9h 30m
1 stop
SJU2:01 amSan Juan Luis Munoz Marin Intl
Apr 17
SJU6:00 amSan Juan Luis Munoz Marin Intl
7h 14m
1 stop
CLE1:14 pmCleveland Hopkins Intl
$196
Frontier
Mar 4
CLE4:47 pmCleveland Hopkins Intl
6h 56m
1 stop
SJU12:43 amSan Juan Luis Munoz Marin Intl
Mar 11
SJU6:39 pmSan Juan Luis Munoz Marin Intl
24h 52m
1 stop
CLE7:31 pmCleveland Hopkins Intl
$199

Delta flights from Cleveland to Caribbean Islands

Our best Delta deals on Cleveland to Caribbean Islands flight tickets
Delta
Mar 2
CLE12:35 pmCleveland Hopkins Intl
10h 21m
1 stop
SJU11:56 pmSan Juan Luis Munoz Marin Intl
Mar 5
SJU6:15 amSan Juan Luis Munoz Marin Intl
8h 07m
1 stop
CLE1:22 pmCleveland Hopkins Intl
$256
Delta
Apr 22
CLE5:50 amCleveland Hopkins Intl
8h 58m
1 stop
STT2:48 pmSaint Thomas Island Cyril E King
Apr 24
STT3:05 pmSaint Thomas Island Cyril E King
9h 29m
1 stop
CLE12:34 amCleveland Hopkins Intl
$270
Delta
Mar 1
CLE6:00 amCleveland Hopkins Intl
9h 22m
1 stop
STT4:22 pmSaint Thomas Island Cyril E King
Mar 6
STT4:15 pmSaint Thomas Island Cyril E King
6h 43m
1 stop
CLE9:58 pmCleveland Hopkins Intl
$295

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 februar 20, 2026.
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

ma. 3/2

6:29 pm-2:53 am

1 stop7h 24m

San Juan Luis Munoz Marin Intl

lø. 5/2

3:18 pm-11:14 pm

1 stop7h 56m

$194

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

fr. 4/10

4:31 pm-2:01 am

1 stop9h 30m

San Juan Luis Munoz Marin Intl

fr. 4/17

6:00 am-1:14 pm

1 stop7h 14m

$196

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

on. 3/4

4:47 pm-12:43 am

1 stop6h 56m

San Juan Luis Munoz Marin Intl

on. 3/11

6:39 pm-7:31 pm

1 stop24h 52m

$199

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

on. 4/22

5:50 am-2:48 pm

1 stop8h 58m

Saint Thomas Island Cyril E King

fr. 4/24

3:05 pm-12:34 am

1 stop9h 29m

$270

ClevelandSanto Domingo

CLE - SDQ

CLESDQ

Cleveland Hopkins Intl

ti. 3/17

6:31 pm-1:38 am

1 stop7h 07m

Santo Domingo Las Americas

ma. 3/23

2:52 am-5:13 pm

1 stop14h 21m

$302

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

on. 4/8

6:31 pm-2:35 pm

1 stop20h 04m

Oranjestad Reina Beatrix

to. 4/16

3:41 pm-4:30 pm

1 stop24h 49m

$311

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

ma. 4/13

6:00 am-1:25 pm

1 stop8h 25m

Montego Bay Sangster Intl

lø. 4/18

1:15 pm-12:05 am

1 stop9h 50m

$312

ClevelandMontego Bay

CLE - MBJ

CLEMBJ

Cleveland Hopkins Intl

lø. 5/9

7:40 pm-11:24 am

2 stops16h 44m

Montego Bay Sangster Intl

ti. 5/12

4:37 pm-12:48 pm

2 stops19h 11m

$317

ClevelandOranjestad

CLE - AUA

CLEAUA

Cleveland Hopkins Intl

ti. 3/24

6:00 am-12:50 pm

1 stop6h 50m

Oranjestad Reina Beatrix

ma. 3/30

4:30 pm-9:52 am

1 stop17h 22m

$353

ClevelandCastries

CLE - UVF

CLEUVF

Cleveland Hopkins Intl

on. 3/18

6:00 am-1:58 pm

1 stop7h 58m

Castries Hewanorra

on. 3/25

3:18 pm-12:29 am

1 stop9h 11m

$464

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 $245. The month of April is another great option to travel to Caribbean Islands, with average flight prices from Cleveland averaging around $278.

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 $218. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $294. 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 $248. 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 morning because they tend to be around $283. 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 Punta Cana 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 $319 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 $260 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

Mon, Wed and Fri

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 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).
  • 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
DeltaPriceFrom $104Free CancellationRating
7.9
8,228 reviews
Search Delta flights
JetBluePriceFrom $154Free CancellationRating
7.2
2,898 reviews
Search JetBlue flights
FrontierPriceFrom $156Free CancellationRating
5.7
3,046 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $180Free CancellationRating
6.3
8,482 reviews
Search Spirit Airlines flights
American AirlinesPriceFrom $216Free CancellationRating
7.2
11,334 reviews
Search American Airlines flights
United AirlinesPriceFrom $225Free CancellationRating
7.4
9,335 reviews
Search United Airlines flights
SouthwestPriceFrom $246Free CancellationRating
8.0
4,298 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.

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1 adult
sø. 3/22
sø. 3/29

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