$105 Find Cheap Flights from Caribbean to Cleveland

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Cleveland departing on 5/16. 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 Caribbean to Cleveland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Cleveland 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 Caribbean to Cleveland

Wed, May 27 - Sun, Jun 7
Frontier Logo
6:00 am - 2:42 pm
SJU
-
CLE
8h 42m
1 stop
Frontier Logo
9:57 pm - 2:46 am
CLE
-
SJU
28h 49m
1 stop
$192Frontier
Wed, May 6 - Sat, May 9
Frontier Logo
2:56 pm - 9:51 pm
SJU
-
CLE
6h 55m
1 stop
Frontier Logo
9:57 pm - 8:04 am
CLE
-
SJU
10h 07m
1 stop
$194Frontier
Wed, May 6 - Wed, May 13
Frontier Logo
6:00 am - 11:11 pm
SJU
-
CLE
17h 11m
1 stop
Frontier Logo
9:57 pm - 8:04 am
CLE
-
SJU
10h 07m
1 stop
$197Frontier
Fri, May 8 - Fri, May 15
American Airlines Logo
11:27 am - 12:26 am
STT
-
CLE
12h 59m
2 stops
American Airlines Logo
7:40 pm - 12:35 pm
CLE
-
STT
16h 55m
1 stop
$290American Airlines
Fri, May 29 - Sat, Sep 12
American Airlines Logo
2:08 pm - 11:49 pm
MBJ
-
CLE
8h 41m
1 stop
American Airlines Logo
8:09 pm - 11:00 am
CLE
-
MBJ
15h 51m
1 stop
$316American Airlines
Fri, May 1 - Mon, May 4
United Airlines Logo
2:20 pm - 11:26 am
PUJ
-
CLE
21h 06m
1 stop
United Airlines Logo
7:55 pm - 3:12 pm
CLE
-
PUJ
19h 17m
1 stop
$367United Airlines
Fri, May 8 - Sun, May 17
United Airlines Logo
2:10 pm - 10:44 pm
STT
-
CLE
8h 34m
1 stop
United Airlines Logo
6:00 am - 12:20 pm
CLE
-
STT
6h 20m
1 stop
$380United Airlines
Thu, May 21 - Wed, May 27
Delta Logo
1:55 pm - 11:20 pm
AUA
-
CLE
9h 25m
1 stop
Delta Logo
7:49 pm - 12:00 pm
CLE
-
AUA
16h 11m
1 stop
$386Delta
Sat, May 9 - Wed, May 13
Delta Logo
1:16 pm - 6:48 pm
NAS
-
CLE
5h 32m
1 stop
Delta Logo
6:00 am - 11:51 am
CLE
-
NAS
5h 51m
1 stop
$458Delta
Fri, May 15 - Fri, May 22
Southwest Logo
8:45 am - 6:00 pm
NAS
-
CLE
9h 15m
2 stops
Southwest Logo
10:55 am - 6:30 pm
CLE
-
NAS
7h 35m
1 stop
$486Southwest
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$105
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 14% lower on average.
Flight from San Juan Airport to Cleveland

FAQs for booking flights from Caribbean to Cleveland

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

    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 Caribbean to Cleveland.

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

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

    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 to Cleveland with an airline and back to Caribbean with another airline.

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

    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 to Cleveland from Caribbean 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 Caribbean to Cleveland

 
Need help choosing which airline to fly with from Caribbean to Cleveland? 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 4330 reviews
8.0Comfort
8.6Crew
7.0Food
8.1Boarding
7.5Entertainment
Airline reviews

The seat was not comfortable. 1D. My back was sore all night and the next day.

8.0 ExcellentJolene, Apr 2026
LAS - DAL
Read more Southwest reviews

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Transparency from pilots, quick boarding and exiting the plane, staff greeted to each and everyone,

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.

Pilots lied about waiting on “paperwork”. Sat in the plane for over an hour, waiting on some papers to be printed according to the pilot and then all of a sudden he says good news maintenance is finally on their way. Maybe they can fix it before we get our paperwork. Ended up missing my connection in LaGuardia and as a result, had a fly home to Lexington instead of the Louisville airport. Then paid $100 to uber to Louisville since it was midnight by the time I got in. I wish they would just be transparent with passengers sometimes and not try to beat around the bush on why things are delayed.

The WiFi was horrific. I fly delta often and love their (usually reliable and free) WiFi. On this flight it was intermittent and when it did connect was extremely slow. I couldn’t get any work done while I was on the flight which was extremely frustrating. I was also in the exit row seat where there is now immediate seat in front of you, so while the leg room was nice, I couldn’t even watch the TV when the internet wasn’t working. Finally, for the last 20 mins of the flight, the announcement indicator came on the TV screens and took them over, even though no announcement was being made. Really disappointed.

The flight was way too HOT! And the plane did not have any in-flight TV entertainment.

The tray table was broken and the food was terrible.

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

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

Dinner was good, but the breakfast served in the morning was horrible.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Lounges are packed and very poor, food is really bad, for business class in an airline is well below expectations

The international / itallian speakers did not seem as friendly and professional as the others. Drink selections were denied ( a beer) until questioned about lack of ANY beer on the plane and then four options were given.

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

It was good. However, I didn’t expect for a delayed flight. Need to catch bus or ride going to Bakersfield since I need to be there the funeral of my Uncle.

I was able to get the AA customer Service desk to put me on an earlier flight without any issues.

The seat was comfortable, the attendants were very nice and WiFi made my life so much easier with work. Kudos!

AA was a very good experience. The employees are wonderful

Flight was 3 hours delayed. They gave our plan to two other routes. Need to knock that off.

To have arrived on time and not 3 hours late after having already spent $100 to change to an earlier flight, only to arrive back home close to the original flight time.

No gate in Rome. Had stairs. Got separated from my wife in a wheel chair. Customs was a zoo. If AA doesnt have landing rights, it should be advertised.

I almost missed my flight and they helped me out enormously

Business class was very good, one of my best flights

The "on the ground" A/C was not working. It was so hot while waiting to get in the air, a passenger from the rear of the plan declared "I just can't!" and waited in the gangway until time to close the doors. It was miserable. But the crew were champs and had an amazing attitude. I know they were as miserable as we were but didn't let that affect their performance.

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

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