$113 Find Cheap Flights from Cleveland to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Caribbean departing on 11/17. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Cleveland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$382
Santo Domingo
Santo Domingo1 stop$347
Montego Bay
Montego Bay1 stop$300
Oranjestad
Oranjestad1 stop$309
Nassau
Nassau1 stop$411
Kingston
Kingston1 stop$363
Simpson Bay
Simpson Bay1 stop$365
Providenciales
Providenciales1 stop$406
Port of Spain
Port of Spain2 stops$573
Bridgetown
Bridgetown2 stops$573
George Town
George Town1 stop$387
Willemstad
Willemstad2 stops$341
St. John's
St. John's1 stop$610
Puerto Plata
Puerto Plata1 stop$480
Aguadilla
Aguadilla2 stops$225
Punta Cana
Punta Cana1 stop$382
Santo Domingo
Santo Domingo1 stop$347
Montego Bay
Montego Bay1 stop$300
Oranjestad
Oranjestad1 stop$309
Nassau
Nassau1 stop$411
Kingston
Kingston1 stop$363
Simpson Bay
Simpson Bay1 stop$365
Providenciales
Providenciales1 stop$406
Port of Spain
Port of Spain2 stops$573
Bridgetown
Bridgetown2 stops$573
George Town
George Town1 stop$387
Willemstad
Willemstad2 stops$341
St. John's
St. John's1 stop$610
Puerto Plata
Puerto Plata1 stop$480
Aguadilla
Aguadilla2 stops$225

Book Cheap Cleveland to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Cleveland to Caribbean

Thu, Nov 20 - Mon, Nov 24
Multiple Airlines Logo
3:40 pm - 4:28 pmCLE-SJU
23h 48m2 stops
Multiple Airlines Logo
5:19 pm - 1:11 pmSJU-CLE
20h 52m1 stop
$256Multiple Airlines
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Thu, Nov 20 - Mon, Nov 24
Frontier Logo
5:30 am - 1:06 amCLE-SJU
18h 36m1 stop
Frontier Logo
3:59 am - 3:32 pmSJU-CLE
12h 33m1 stop
$258Frontier
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Sat, Dec 6 - Sat, Dec 13
United Airlines Logo
12:33 pm - 12:36 amCLE-SJU
11h 03m2 stops
United Airlines Logo
8:10 am - 4:41 pmSJU-CLE
9h 31m1 stop
$259United Airlines
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Thu, Jan 1 - Sat, Jan 10
Frontier Logo
7:59 pm - 1:24 amCLE-SJU
4h 25mnonstop
Frontier Logo
3:55 am - 7:53 amSJU-CLE
28h 58m1 stop
$260Frontier
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Tue, Dec 9 - Fri, Dec 12
American Airlines Logo
6:01 am - 5:52 pmCLE-SJU
10h 51m2 stops
American Airlines Logo
7:00 am - 4:33 pmSJU-CLE
10h 33m1 stop
$271American Airlines
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Tue, Mar 3 - Wed, Mar 4
American Airlines Logo
6:00 am - 4:09 pmCLE-SJU
9h 09m1 stop
American Airlines Logo
9:25 am - 6:16 pmSJU-CLE
9h 51m1 stop
$285American Airlines
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Sat, Nov 15 - Thu, Nov 20
United Airlines Logo
11:00 am - 10:22 pmCLE-SJU
10h 22m2 stops
United Airlines Logo
2:05 am - 9:37 amSJU-CLE
8h 32m1 stop
$298United Airlines
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Sat, Nov 29 - Sat, Dec 6
Delta Logo
6:00 am - 3:20 pmCLE-AUA
8h 20m1 stop
Delta Logo
4:35 pm - 12:27 amAUA-CLE
8h 52m1 stop
$322Delta
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Thu, Jan 1 - Wed, Jan 7
Delta Logo
7:30 am - 3:20 pmCLE-AUA
6h 50m1 stop
Delta Logo
4:35 pm - 12:39 amAUA-CLE
9h 04m1 stop
$380Delta
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Wed, Dec 31 - Sun, Jan 4
Southwest Logo
5:50 am - 1:45 pmCLE-PLS
7h 55m2 stops
Southwest Logo
2:40 pm - 12:05 amPLS-CLE
9h 25m2 stops
$1,371Southwest
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Booking Insights

KAYAK's insights & trends for Cleveland to Caribbean flights

Get data-powered insights and trends into flights from Cleveland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Cleveland to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean from Cleveland found in the last 72 hours was to San Juan, at $362 round-trip. The most popular route is from Cleveland (CLE) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $362.

Can I save money by flying with a layover from Cleveland to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $506, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Cleveland to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Cleveland to Caribbean is May, when tickets cost $266 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $481 and $389 respectively.

What’s the cheapest day of the week to fly from Cleveland to Caribbean?

The average price of all round-trip flights from Cleveland to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Saturday. On your return trip to Cleveland, you should consider flying back on a Wednesday, and avoid Tuesdays for better deals.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Cleveland to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Cleveland to Caribbean, you should book around 2 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$113
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Cleveland to San Juan Airport

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Cleveland to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Cleveland to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Cleveland to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Cleveland to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Cleveland to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Cleveland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $257 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $348.

  • How many flights are there between Cleveland and Caribbean per day?

    There is a maximum of 1 nonstop flight a day that takes off from Cleveland and lands in Caribbean, with an average flight time of 4h 17m. The most common departure time is 12:00 pm and most flights take off in the morning. Each week, there are 3 flights.

Reviews of the top 5 airlines serving from Cleveland to Caribbean

 
Need help choosing which airline to fly with from Cleveland to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4243 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025OAK - BUR
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

Flight delayed and missed connection. Rescheduled flight cancelled after 6 hrs wait. Rerouted thru ORD, flight cancelled, overnight stay in ORD. Still in the air on new flight!

We are too tired and frustrated to comment politely at this point

Terrible. Our luggage was delayed and couldn’t be delivered for several days. We got bad information from the airline agents at baggage claim. We had to pick up our car so we wouldn’t be charged for an extra day. We got lost in the maze of airport parking. The baggage claim agents didn’t offer us any compensation for our extra time and expense. We are tired, hungry and very frustrated.

The flight was flawless and we even arrived between 20 and 25 minutes early!

The only thing to like was that we eventually got to our destination

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

The single worst check in experience I could imagine. I’ll never do any business with Frontier or any affiliated company

Too many extra fees, uncomfortable, little leg room. Will not recommend this airline.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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