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$68 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 6/4. 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
0 bags
Thu 6/20
Thu 6/27

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Good to know

Low season

March

High season

July

Cheapest flight

$68
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly with an average 3% increase in price.
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.

See more FAQs

Prefer to fly non-stop from Caribbean to Cleveland?

Find which airlines fly direct from Caribbean to Hopkins Intl, which days they fly and book direct flights.

Nonstop departures

Caribbean to Cleveland Hopkins Intl

Monday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Tuesday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Wednesday

ANA, Aer Lingus, Aeromexico, +48 more

ANA, Aer Lingus, +49 more

Thursday

ANA, Aer Lingus, Aeromexico, +45 more

ANA, Aer Lingus, +46 more

Friday

ANA, Aer Lingus, Aeromexico, +47 more

ANA, Aer Lingus, +48 more

Saturday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Sunday

ANA, Aer Lingus, Aeromexico, +48 more

ANA, Aer Lingus, +49 more

See more direct flights

Nonstop returns

Cleveland Hopkins Intl to Caribbean

Monday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Tuesday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Wednesday

ANA, Aer Lingus, Aeromexico, +48 more

ANA, Aer Lingus, +49 more

Thursday

ANA, Aer Lingus, Aeromexico, +45 more

ANA, Aer Lingus, +46 more

Friday

ANA, Aer Lingus, Aeromexico, +47 more

ANA, Aer Lingus, +48 more

Saturday

ANA, Aer Lingus, Aeromexico, +46 more

ANA, Aer Lingus, +47 more

Sunday

ANA, Aer Lingus, Aeromexico, +48 more

ANA, Aer Lingus, +49 more

See more direct flights
See more direct flights

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
DeltaOverall score based on 10615 reviews
7.9Comfort
8.6Crew
8.0Entertainment
7.4Food
8.2Boarding
Airline reviews

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

8.0 ExcellentDavid, May 2024SJU - JFK
Read more about Delta reviews

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

The 676 plane is much more comfortable in business class than the A330 and he food was a little better. I didn’t use the entertainment.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

They were an hour late and they didn’t have my wheelchair for me

The Flight crew didn’t serve us until about 1.5 hours into the flight because of turbulence but after it ended it was fine to move around. They served us water only and snacks and then NEVER, NOT ONE TIME came through to collect trash until right before landing about 1.5 hours later. There was absolutely no need for that. They crew was just standing around talking and visiting with each other and really never tried to see if we might want something besides water or even try to come pick up trash. This is VERY unusual for a Delta flight but it was not what I would have expected for a 4 hour flight.

The 1st class male crew member was very pleasant - the short female with round glasses , maybe in 50’s had no personality- never spoke when delivering my food, drink, & never smiled the whole trip! In fact looked annoyed when the boarding proses was happening- I would never hire this woman - unfriendly . Have never dealt with a crew member like her-

5-hour delay due to storms in Tanoa and airspace restricted by Miami traffic controllers.

A regional sized plane was used for a cross country flight with no overhead bin space. I had to "pink check" my laptop and my medications. I was NOT pleased!!!!

Fantastic. Smooth boarding with an infant. Never experienced it with any other carriers.

This was a Lufthansa flight, not United. The CSA at the counter, Ashley, was not only incompetent, but quite rude. Me and two other PAX waited over 7 minutes standing in front of her and another CSA and they ignored us. We joked that we must have accidently taken invisibility pills. She could have at least said "I'll be with you in a moment, I'm currently....". I could go on about how rude she and the other CSAs were (whispering, not communicating with me, blaming the situation on others, etc.). She would not work for me. Then, she gave me literally the worst seat on the plane. the worst. My seat kept getting bumped (rammed twice by the crew with their carts and about every 5 minutes by someone using the bathroom), listening to the bathroom all night, crowded seat, etc.

My seat was broken. WiFi didn’t work. Gate crew at HOU were rude and condescending. Treated all the passengers badly. Bad experience, United.

First flight of the day… MINIMUM FUEL! 15 minute landing delay at HOU due to fog turned into a 2+ hour delay! Rather than circle, they had to divert to another city to refuel! Sat on tarmac at Austin to refuel. We ALL missed our connections! The crew, including pilots, were clueless. Crew was really a mess. At HOU, Untied employees were exceedingly rude to all. It was pitiful.

The check in from Panama to Houston was good. From Houston to Toronto was definitely an experience. The Pilot from Houston to Toronto was exceptional. He probably saved our lives by noticing a dent in the fuselage. Everyone was taken off the plane and we boarded a new plane

An hour and a half late is UNACCEPTABLE. The negative impact to our family is unconscionable. And for the price we were forced to pay...

We enjoyed that we boarded and took off on time. We didn’t like that our connection flight was a twenty minute walk through the airport with only one hour in between flights.

No lounge access with “United First” ticket. False alarm about late flight, jeopardizing connection. Wrong meal. Loose power socket would not hold plug, could not charge device. In-flight access to text messaging did not work. Toilet seat on plane would not stay up.

We ended up with seats in the very back. So they did not recline. Have no idea why, we reserved and checked in very early. The isles were very narrow and the seats had very little leg room. But they did give us water, and a snack.

Boarding was terrible. My wife uses a wheel chair and she was in an incredibly hot closed metal cargo box for close to 20 minutes before getting on board

Delayed so that missed connecting flight. Connecting flight was also delayed on the tarmac but they closed the gate before the rescheduled time.

Attendants were rude. Scowling. Seats were miserable and we paid extra.

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

2 hour flight with no drink service from the bahamas?!! There was very little turbulence and the turbulence didnt seem to affect first class drink service. I understand that they may not be able to pour all kinds of drinks, but thye can hand out bottles of water at lease

As no headphones/ ear pieces in back of seat for entertainment system, would have been to been offered rather than asking & waiting a long time. I know we are in economy but cost of ticket was high.

The flight was short. However, my bag was delayed and was put on another flight.

Flight attendant was incredible. Very efficient, friendly and pleasant. Patricia was one of the best I have ever seen. Please give her a big raise!

LIT to DFW - 3 hours late; the entire plane had been boarded before they told us there was a delay due to a weather-related ground stop in Dallas. DFW to MAY - 2+ hours late due to A/C needing to be repaired after everyone had boarded, then when we finally reach the runway, the First Officer timed out and we had to taxi all the way back to the gate and wait for a new one. I arrived in New Orleans 5+ hours later than I should have. Return flights were completely cancelled; rebooked through the app to fly through CLT instead of DFW. MSY to CLT had no issues, but CLT to LIT was delayed 1.25 hrs because flight attendants had not arrived to the airport yet. At least they didn’t make us all sit on the plane to wait for them. I should have driven.

Tray table was filthy when I sat down. I needed to have someone come clean it because there was food and stains on it WiFi didn’t work after paying for in-flight WiFi. Food was terrible and was not filling at all Chicken was rubbery Flight attendant had an attitude, interrupted me and wasn’t able to answer basic questions about the food selection such as “does the chicken have red sauce in it”. If your flight attendants are not going to know what is in the meals so we can make an educated decision based on dietary restrictions, they shouldn’t be on the plane. My 1.5 year old niece was sleeping and dropped her binkie. I went on the ground under the chairs looking for it. It was at that time that she came up to me as I’m CLEARLY on all 4s with a flashlight and said “I need to get by”. I said one moment please I’m getting something from under the seat (while my head was literally under the seat). Her reply was “no you need to move now” and proceeded to almost push me out of the way. I looked up and all I saw was her toes under my eyes. When I looked in front of me, her private parts were inches away from my face. I then made a comment “you couldn’t waited 2 seconds?” and her response was, “no I need to use the bathroom”. I understand that and would never want to be the reason someone couldn’t get to the bathroom but I was under the seat. She could’ve gone around the other way instead of harassing me, basically placing her private parts on my head and borderline pushing me out of the way. You don’t pay that much for this deplorable experience. This was by far the worst experience I have ever had on American. I will be absolutely thinking twice and thrice about flying American Airlines again. I would rather pay more to fly delta because at least I know their WiFi will work and their flight attendants won’t have a shitty attitude for no reason, nor will they act the way this woman did. Unacceptable.

Liked - nothing. Disliked - delayed 35+ min sitting on the plane. Caused me to miss my connection in Charlotte. American Airlines is the worst US Air Carrier company with atrocious customer service.

It was the worst ever, i will be filing a lawsuit to get a refund. Our flight was delayed 4 hours so we would miss our connecting flight, we were not rebooked to our destination the same day, we were not offered any options to get home on the same day despite being clear that we absolutely cannot get stranded at night due to family, we were forced to book our own flights on a different airline to get home, and spririt is refusing a refund because our flight wasn't cancelled, only delayed. oh yeah, and they lost our luggage on the first part of the trip and you cannot get a hold of customer service when anything goes wrong, on hold for 30+ minutes. and their app breaks so you can't use that either.

This recognisable no-frills airline gets me from point-A to point-B. I was able to get to Chicago without stress. The checked baggage collection and reclaim could be improved.

The crew was the best and very accommodating I know you don't offer any complimentary items but water and coffee will not break the bank !!

My flight was cancelled!!! I had to spend 200.00 on another flight!!

The whole day was a nightmare. Flight extremely late. Boarding was a mess of a nightmare.

When we landed, they kept us on the plane for almost 25 minutes. Could do better.

worst trip ever Spirit lost our Baggs which were never put on the plane in Atlanta. 24 hours ago they are telling me now that the bags are still missing.

Never been on this flight as i had missed it due to delayed connecting flight

Horrible. Delays, no customer support and fake promises and everything. i am suffering to help as due to connecting flight getting missed no support on ground and customer support window is closed and we are sitting o ground without anything

Missed our departing flight due to poor baggage drop staff. At the airport with 2 & 1/2 hours to spare and waited in bag check in until 15 minutes prior to gates closing before baggage staff asked us to move to the front of the line. We weren’t the only passengers that missed the flight. Poor organizational operations by Spirit staff. Otherwise , the return trip was fine.

Plane could have been more on time. More leg room .

I arrived 1 hour prior to boarding, and they said I was too late for a domestic flight. First time I heard that :-(

Check in online was easy. Seats aren’t very comfortable

Fecal matter in seat back pocket. Presumably from a kids diaper.

Worst airline to travel with. They treat you like a prisoner in a jailhouse barking out orders and threats. Nickle and dime you to the same price or higher than a respectable airline like one of the big 3 . Might as well fly with standard airlines

Well I mean u get what u pay for so 🤷‍♂️

Over an hour delay in departure but I was notified beforehand. Another delay on tarmac upon arrival at LGA. We ended up departing the plane almost 2 hours later than expected

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.

I checked a bag because it was $5 less than carry on. They managed to lose my bag on a 2.5 hr direct flight! Frontier has no airport staff at baggage claim to help. As soon as I got home around 11 pm I tried to use their online system to file the claim for lost bag - system wouldn't take the # on my baggage claim ticket - said it was not the correct number. Also said that I had not checked a bag, which wasn't true - even my online boarding pass showed that I had checked a bag. Wasted about an hour on that process with no luck. Tried again in the morning - same thing. So tried online chat with Frontier bot - waited 35-40" twice to be connected to a baggage agent and it never happened. Eventually drove to PDX after work and waited 2 hrs for the Frontier ticket agents to arrive prior to the next Frontier flight out of PDX and FINALLY got some help from one of them, to take me to lost luggage area where I was able to retrive my bag. Probably took 4-5 hrs. of my time and endless frustration to get my bag. This was my first -- and LAST -- experience flying Frontier Airlines. Check-in was also extremely difficult and time consuming. The flight itself (and staff) were fine but everything else about the experience was a total disaster! The fact that Frontier literally has NO WAY to connect to a human voice for customer service (in this case for lost luggage) is the WORST!!!!!

Frontier is a crappy airline nothing about it is honest

Book cheap flights from Caribbean to Cleveland

Recent round-trip flight deals

5/30Thu
nonstopFrontier
4h 51mSJU-CLE
6/3Mon
nonstopFrontier
4h 19mCLE-SJU
$157
5/30Thu
nonstopFrontier
4h 51mSJU-CLE
6/3Mon
nonstopFrontier
4h 19mCLE-SJU
$158
6/5Wed
1 stopSpirit Airlines
9h 35mSJU-CLE
6/12Wed
1 stopSpirit Airlines
12h 30mCLE-SJU
$212
8/14Wed
1 stopSpirit Airlines
6h 50mSJU-CLE
8/21Wed
1 stopSpirit Airlines
6h 28mCLE-SJU
$228
10/1Tue
2 stopsAmerican Airlines
7h 38mSJU-CLE
10/8Tue
2 stopsAmerican Airlines
7h 48mCLE-SJU
$321
9/30Mon
2 stopsAmerican Airlines
10h 45mSJU-CLE
10/8Tue
1 stopAmerican Airlines
14h 39mCLE-SJU
$323
9/27Fri
1 stopDelta
9h 43mNAS-CLE
10/1Tue
1 stopDelta
5h 13mCLE-NAS
$393
9/13Fri
1 stopDelta
7h 44mPLS-CLE
9/20Fri
1 stopDelta
5h 44mCLE-PLS
$432
6/24Mon
1 stopUnited Airlines
10h 39mPOS-CLE
8/11Sun
1 stopUnited Airlines
17h 08mCLE-POS
$521
6/24Mon
1 stopUnited Airlines
15h 30mPOS-CLE
8/12Mon
1 stopUnited Airlines
32h 33mCLE-POS
$539

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Recent one-way flight deals

6/4Tue
1 stopSpirit Airlines
25h 37mSJU-CLE
$68
5/30Thu
nonstopFrontier
4h 51mSJU-CLE
$79
6/6Thu
nonstopFrontier
4h 48mSJU-CLE
$80
6/4Tue
3 stopsSpirit Airlines
34h 22mSJU-CLE
$90
5/30Thu
2 stopsAmerican Airlines
10h 10mSJU-CLE
$162
10/14Mon
1 stopUnited Airlines
9h 13mSJU-CLE
$205
11/16Sat
1 stopAmerican Airlines
7h 23mSJU-CLE
$206
6/9Sun
1 stopUnited Airlines
9h 05mSJU-CLE
$246
9/30Mon
1 stopDelta
9h 43mNAS-CLE
$276
10/26Sat
1 stopDelta
8h 09mPUJ-CLE
$285

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Last minute flights from Caribbean to Cleveland

Last minute flight, train and bus deals

5/23Thu
nonstopFrontier
4h 51mSJU-CLE
5/27Mon
nonstopFrontier
4h 19mCLE-SJU
$177
5/23Thu
nonstopFrontier
4h 51mSJU-CLE
5/29Wed
nonstopFrontier
4h 19mCLE-SJU
$178
5/23Thu
multi-stopSpirit Airlines
9h 10mSDQ-CLE
5/27Mon
multi-stopSpirit Airlines
10h 16mCLE-SDQ
$282
5/25Sat
multi-stopSpirit Airlines
6h 16mSJU-CLE
6/8Sat
multi-stopSpirit Airlines
12h 52mCLE-SJU
$286
5/23Thu
multi-stopAmerican Airlines
9h 39mSJU-CLE
5/28Tue
multi-stopAmerican Airlines
9h 18mCLE-SJU
$402
5/23Thu
multi-stopAmerican Airlines
9h 52mSJU-CLE
5/27Mon
multi-stopAmerican Airlines
11h 57mCLE-SJU
$404
5/22Wed
multi-stopUnited Airlines
15h 42mSJU-CLE
5/27Mon
multi-stopUnited Airlines
6h 29mCLE-SJU
$495
5/23Thu
multi-stopUnited Airlines
9h 05mSJU-CLE
6/1Sat
multi-stopUnited Airlines
15h 24mCLE-SJU
$518
5/22Wed
multi-stopDelta
11h 13mSDQ-CLE
5/26Sun
multi-stopDelta
18h 36mCLE-SDQ
$532
5/22Wed
multi-stopDelta
11h 13mSDQ-CLE
5/26Sun
multi-stopDelta
11h 45mCLE-SDQ
$596

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Flights to Cleveland