$125 Find Cheap Flights from Cleveland to Caribbean Islands - Compare and Save

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Cheap Flights from Cleveland to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan
4h 25mNonstop
from $254per person
Oranjestad
6h 40m2 stops
from $306per person
Nassau
4h 45m2 stops
from $352per person
Simpson Bay
6h 50m2 stops
from $362per person
Providenciales
5h 50m2 stops
from $381per person
Willemstad
7h 22m2 stops
from $386per person
Punta Cana
4h 10mNonstop
from $388per person
Christiansted
7h 35m2 stops
from $398per person
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Booking Insights

KAYAK's insights & trends for Cleveland to Caribbean Islands flights

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

What is the cheapest Cleveland to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from Cleveland found in the last 5 days was to San Juan, at $235 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 5 days was $235.

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

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $490 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $750.

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

No, with an average price for the route of $395, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Cleveland to Caribbean Islands is February, when tickets cost $568 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $696 and $654 respectively.

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

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

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

To get a below average price on the flight from Cleveland to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 15% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low season

October

Cheapest flight

$125
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Cleveland to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Cleveland to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Cleveland to Caribbean Islands

 
Need help choosing which airline to fly with from Cleveland to Caribbean Islands? 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.
7.8
DeltaOverall score based on 8564 reviews
7.8Comfort
7.8Entertainment
7.2Food
8.1Boarding
8.5Crew
Airline reviews

wifi too slow or would not connect and entertainment kept on freezing

4.0 OkayAlexander, Aug 2026
Read more Delta reviews

wifi too slow or would not connect and entertainment kept on freezing

The flight was over 2 hours late.. once we finally got boarded things were fine

Didn't like sitting on the waiting pad for 30 minutes right after departing the gate. If you're going to do that, just don't board so people can still get up and walk around in the terminal. My luggage was damaged by the baggage handlers.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Only water, tea or coffee served midflight, even to comfort seating. Man next to me needed two seats and took up a portion of my seat and Delta did nothing.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

Delta made it easy, comfortable and timely. The crew was fantastic.

Flight was delayed 14 hours due to DC air show and weather. Missed connection to MUC.

The entertainment options on the seat back video boards were nice.

There was no WiFi available, there were mechanical problems with the plane and we landed at C 124, then the gate was switched to A 26, then all the way back to C126! For a 75 yo woman traveling alone, this was a difficult journey, indeed!

Teeny tiny bathrooms, crew was not realistic about when we'd arrive.

Very bad! They kept delaying my flight and wouldn’t do anything about it

IAD with the archaic people movers is just a place to be avoided.

Cabin was pitch black, even during meal service. The reading lights for seat 2E/F did not work, and seat 2E did not recline.

The flight from Cleveland to Newark was great. The connecting flight wasn’t so good.

Flight was not comfortable and crew was rude and not wanted to help, i would never choose united if there is alternate options . not cooperative with baby

Seat comfort is still an issue. Seats way too hard or lacking lumbar support. Entertainment system has lots of nice features like “Don’t wake me for meals”. The Bluetooth headphone pairing works well if you know how to make your pods available for pairing. While this trip I didn’t find any of the many many movies that interesting, there is plenty in there for all tastes. Crew were excellent. Captain was good about telling us how limg seat belt sign would be on while going around a storm system. Wi-Fi was quite good for only $8 bucks for mileage plus members. Be sure to load a credit card into your United app to pay for food or drinks.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

It was a code share with Alaska - would have been great if I actually made it on the plane, claimed I didn’t have a ticket or a seat even thought I was checked in.

Plenty of overhead space but forced to check my carry-ons both legs

The flight from CLE to JFK was fantasti! Pilots and cre were informative and accommodating.

Everything was ok except that we had to de-ice the plane which took about 20 mins. I realize this is a safety issue, but it caused us to miss a connection in Charlotte by 15 mins which meant a four hour layover. I think the thing that bothered me was American Airlines knew we were only 15 mins late, so couldn’t they have waited for us? There were about 10 of us that had to take alternate planes. I remember recently waiting 15 to 20 mins for passengers connecting with flights we were on. Just wondering why they couldn’t do the same for ours.

Another American flight delay. Gate staff was gratuitously abusive of anyone expressing frustration. This will be my last American Airlines flight

Abysmal, getting delayed approximately 13 times, having to switch out a crew with another crew that timed out within an hour, and customer service representatives that abandoned the stranded travelers. Terrible service

Flight attendants used to be nice to people. And any flight over 5 hours should have some kind of food other than tiny pretzels and one drink comped.

Good experience with this flight. Boarding was smooth with no issues. The short flight was good with quick drink & snack service. Nice easy way to get back from DC.

Very good flight that left on time and arrived earlier than anticipated, which was a plus! The crew members were very welcoming and helpful. However, the temperature on the flight was very cold - almost to the point of extreme discomfort. Additionally, requiring passengers to pay $8 for headphones to access the JetBlue entertainment was disappointing. Those earbud jacks are not used with most technology and would not be able to be used. There was no option to use Bluetooth for my own earbuds. Beyond those inconveniences, the flight was good.

My original flight was cancelled. My replacement flight was delayed over 2 hours. I lost my whole day in NY

Delays were crazy long (over an hour) both for boarding and baggage claim

awful expereince. boarding was a mess and not communicated, then we sat on a hot plane and were at risk of getting kicked off

2 hour delay and a lack of air conditioning on the plane. Not a good combination

Complete and total debacle from start to finish. HUGE mistake picking this airline. NEVER again! Rudest staff in the business.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

There was a screen but no earphones that could use the older input so I could listen to anything.

If jet blue is going to offer tv at every seat, fix the headphone connection so you can hear. Haven’t had a usable headphone jack in years

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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.

Finally a Frontier on time and efficient. I've had problems before with your airline, but this time everything went fine.

My costume jewelry was stolen out of my bag. Got to airport and my bag weighed 45 pounds- 5 pounds over cost me $100 Long lines in tier one. No entertainment No WiFi no free drinks or snacks

I did not like that people are purposely split ip who book at the same time because we didn’t buy seats. No other airline does that.

There was extremely long wait times to check in my bags and pass through TSA. I almost missed my flights on several occasions.

On both our outgoing flight and our return flight, Frontier split up our seats. We were two adults and two small children, one an infant. Both flights were only about half full with full rows of empty seats. Yet, the airline split us up. No, we did not spend the extra $40 per person each way to purchase seat assignments ahead of time. But should we have to do this? If so, then the advertised ticket price was $40 off. What makes this even more egregious is that the plane was not full. So, there was no reason for Frontier to split up our group other than to extract an extra $320. A stewardess even had the nerve to tell me “if you want your family to sit together, I recommend that you purchase seat assignments next time.” On a half empty flight? Ridiculous. We will not be flying Frontier again.

The Frontier app wasn’t working. So I could not pay for a carry on the week prior to flying. They charged me 99$ at the gate to carry on a duffle bag.

I fly Frontier because it’s affordable. I understand that the seats are tight and not the most comfortable…but that’s part of it. The problem with this flight was that there was a group of travelers directly behind me at the back of the plane who were ridiculously loud and obnoxious the entire flight. I’m pretty sure they were drunk and I could periodically smell an odd odor that I believe was one of them using a smokeless vape pen. The stewards had to remind them to keep quiet during the pre-flight instruction, but that was it. They never said another thing to them for the rest of the flight. It was a miserable.

Flight delayed 3 times, resulting in late arrival, rental car place gave car away resulting in increased BS charges because I was late. Frontier blows.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental