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Cheap flights from Cleveland to Caribbean Islands from $88

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 10/27. 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 Islands

Cheap round-trip flights

American Airlines Logo
12:48 pm - 11:59 pmCLE-SJU
11h 11m1 stop
American Airlines Logo
1:50 pm - 12:15 amSJU-CLE
10h 25m1 stop
$175American Airlines
Find Deal
Fri, Oct 24 - Tue, Oct 28
United Airlines Logo
7:00 am - 1:45 pmCLE-SJU
6h 45m1 stop
United Airlines Logo
1:05 am - 9:23 amSJU-CLE
8h 18m1 stop
$187United Airlines
Find Deal
Sun, Sep 7 - Thu, Sep 11
American Airlines Logo
1:05 pm - 11:59 pmCLE-SJU
10h 54m1 stop
American Airlines Logo
5:30 am - 5:49 pmSJU-CLE
12h 19m1 stop
$190American Airlines
Find Deal
Wed, Oct 15 - Sat, Oct 18
Delta Logo
5:20 am - 12:52 pmCLE-SJU
7h 32m1 stop
Delta Logo
1:10 pm - 11:05 pmSJU-CLE
9h 55m1 stop
$205Delta
Find Deal
Mon, Oct 20 - Sat, Oct 25
Delta Logo
5:30 am - 12:59 pmCLE-SJU
7h 29m1 stop
Delta Logo
7:15 am - 5:18 pmSJU-CLE
10h 03m1 stop
$215Delta
Find Deal
Sat, Oct 4 - Sat, Oct 11
Spirit Airlines Logo
4:45 pm - 9:44 amCLE-STT
16h 59m1 stop
Spirit Airlines Logo
10:49 am - 6:56 pmSTT-CLE
8h 07m1 stop
$232Spirit Airlines
Find Deal
Sat, Sep 13 - Thu, Sep 18
Spirit Airlines Logo
4:45 pm - 11:04 amCLE-SJU
18h 19m1 stop
Spirit Airlines Logo
1:59 am - 3:50 pmSJU-CLE
13h 51m2 stops
$233Spirit Airlines
Find Deal
Sat, Sep 20 - Fri, Sep 26
Frontier Logo
11:37 am - 4:07 pmCLE-SJU
4h 30mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$242Frontier
Find Deal
Mon, Aug 11 - Fri, Aug 15
Frontier Logo
11:37 am - 4:07 pmCLE-SJU
4h 30mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$251Frontier
Find Deal
Mon, Aug 11 - Fri, Aug 15
United Airlines Logo
6:00 am - 2:44 pmCLE-SJU
8h 44m1 stop
United Airlines Logo
1:05 am - 1:19 pmSJU-CLE
12h 14m2 stops
$252United Airlines
Find Deal
Sat, Sep 20 - Fri, Sep 26

United Airlines flights from Cleveland to Caribbean Islands

Our best United Airlines deals on Cleveland to Caribbean Islands flight tickets
United Airlines
Sep 7
CLE7:00 amCleveland Hopkins Intl
6h 45m
1 stop
SJU1:45 pmSan Juan Luis Munoz Marin Intl
Sep 11
SJU1:05 amSan Juan Luis Munoz Marin Intl
8h 18m
1 stop
CLE9:23 amCleveland Hopkins Intl
$187
Find similar
United Airlines
Sep 20
CLE6:00 amCleveland Hopkins Intl
8h 44m
1 stop
SJU2:44 pmSan Juan Luis Munoz Marin Intl
Sep 26
SJU1:05 amSan Juan Luis Munoz Marin Intl
12h 14m
2 stops
CLE1:19 pmCleveland Hopkins Intl
$252
Find similar
United Airlines
Oct 4
CLE11:15 amCleveland Hopkins Intl
12h 42m
2 stops
SJU11:57 pmSan Juan Luis Munoz Marin Intl
Oct 11
SJU3:56 pmSan Juan Luis Munoz Marin Intl
8h 02m
1 stop
CLE11:58 pmCleveland Hopkins Intl
$265
Find similar

Frontier flights from Cleveland to Caribbean Islands

Our best Frontier deals on Cleveland to Caribbean Islands flight tickets
Frontier
Aug 7
CLE11:37 amCleveland Hopkins Intl
28h 52m
1 stop
STT4:29 pmSaint Thomas Island Cyril E King
Aug 11
STT5:14 pmSaint Thomas Island Cyril E King
25h 09m
1 stop
CLE6:23 pmCleveland Hopkins Intl
$191
Find similar
Frontier
Aug 11
CLE11:37 amCleveland Hopkins Intl
4h 30m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Aug 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 37m
CLE10:37 amCleveland Hopkins Intl
$242
Find similar
Frontier
Aug 11
CLE11:37 amCleveland Hopkins Intl
4h 30m
SJU4:07 pmSan Juan Luis Munoz Marin Intl
Aug 15
SJU6:00 amSan Juan Luis Munoz Marin Intl
4h 37m
CLE10:37 amCleveland Hopkins Intl
$251
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 July 31, 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

Fri 10/24

12:48 pm-11:59 pm

1 stop11h 11m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:50 pm-12:15 am

1 stop10h 25m

$175

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sun 9/7

7:00 am-1:45 pm

1 stop6h 45m

San Juan Luis Munoz Marin Intl

Thu 9/11

1:05 am-9:23 am

1 stop8h 18m

$187

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Wed 10/15

1:05 pm-11:59 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Sat 10/18

5:30 am-5:49 pm

1 stop12h 19m

$190

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 10/20

5:20 am-12:52 pm

1 stop7h 32m

San Juan Luis Munoz Marin Intl

Sat 10/25

1:10 pm-11:05 pm

1 stop9h 55m

$205

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 10/4

5:30 am-12:59 pm

1 stop7h 29m

San Juan Luis Munoz Marin Intl

Sat 10/11

7:15 am-5:18 pm

1 stop10h 03m

$215

ClevelandSaint Thomas Island

CLE - STT

CLESTT

Cleveland Hopkins Intl

Sat 9/13

4:45 pm-9:44 am

1 stop16h 59m

Saint Thomas Island Cyril E King

Thu 9/18

10:49 am-6:56 pm

1 stop8h 07m

$232

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 9/20

4:45 pm-11:04 am

1 stop18h 19m

San Juan Luis Munoz Marin Intl

Fri 9/26

1:59 am-3:50 pm

2 stops13h 51m

$233

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 8/11

11:37 am-4:07 pm

Nonstop4h 30m

San Juan Luis Munoz Marin Intl

Fri 8/15

6:00 am-10:37 am

Nonstop4h 37m

$242

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Mon 8/11

11:37 am-4:07 pm

Nonstop4h 30m

San Juan Luis Munoz Marin Intl

Fri 8/15

6:00 am-10:37 am

Nonstop4h 37m

$251

ClevelandSan Juan

CLE - SJU

CLESJU

Cleveland Hopkins Intl

Sat 9/20

6:00 am-2:44 pm

1 stop8h 44m

San Juan Luis Munoz Marin Intl

Fri 9/26

1:05 am-1:19 pm

2 stops12h 14m

$252

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 $267. The month of June is another great option to travel to Caribbean Islands, with average flight prices from Cleveland averaging around $277.

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 $227. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around $317. 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 evening. momondo users have found flights departing from Cleveland to Caribbean Islands in the evening 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 $313 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 $254 on momondo.

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

There are 1 cabin classes 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

Best Price Found

$88

Fastest flight time

4h 24m

Direct flights

Every day

Airports in Caribbean Islands

9 airports
The best one-way flight to Caribbean Islands from Cleveland in the past 72 hours is $88. The best round-trip flight deal from Cleveland to Caribbean Islands found on momondo in the last 72 hours is $175.
The fastest flight from Cleveland to Caribbean Islands takes 4h 24m
Direct flights go from Cleveland to Caribbean Islands every day.
There are 9 airports near Caribbean Islands: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Montego Bay Sangster Intl (MBJ), Punta Cana (PUJ), Christiansted Henry Rohlsen (STX), Providenciales (PLS), Simpson Bay Princess Juliana (SXM), Oranjestad Reina Beatrix (AUA), San Juan Luis Munoz Marin Intl (SJU)
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  • 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
8,049 reviews
Search Spirit Airlines flights
FrontierPriceFrom $145Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
DeltaPriceFrom $181Free CancellationRating
8.0
7,981 reviews
Search Delta flights
JetBluePriceFrom $203Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
United AirlinesPriceFrom $241Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $289Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $319Free CancellationRating
8.0
4,246 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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