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Find cheap flights from Cleveland to Caribbean from $39

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 5/15. 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 5/30
Thu 6/6

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$208
Montego Bay
Montego Bay1 stop$269
Santo Domingo
Santo Domingo1 stop$214
Oranjestad
Oranjestad1 stop$304
Nassau
Nassau1 stop$395
Kingston
Kingston1 stop$403
Simpson Bay
Simpson Bay1 stop$283
Providenciales
Providenciales1 stop$413
Port of Spain
Port of Spain1 stop$567
Bridgetown
Bridgetown2 stops$374
George Town
George Town1 stop$491
Aguadilla
Aguadilla1 stop$218
Willemstad
Willemstad1 stop$471
St. John's
St. John's1 stop$615

Good to know

Low season

September

High season

May

Cheapest flight

$39
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from Cleveland to San Juan

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 to Caribbean from Cleveland 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 to Caribbean with an airline and back to Cleveland 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 to Caribbean from Cleveland up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 19% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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
DeltaOverall score based on 10895 reviews
8.2Boarding
7.9Comfort
8.6Crew
8.0Entertainment
7.4Food
Airline reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

6.0 GoodJames, Apr 2024TPA - RDU
Read more about Delta reviews

Delayed due to an ill passenger after loading. Not preventable on Delta's part. Was in first class. The seats are becoming worn and detaching from their velcro attachments. Only got snacks on flight. The attendant was not the friendliest.

I would fly again the whole experience was great. The only feed back I can give that they don't do that American Airlines does is the crew there is more humorous with boarding and thank their passengers. It makes it more fun to fly with them. I would however fly Delta again.

Big plane, long flight, absolutely no leg room and basically non existent air! I am 5”4’ and always travel Main Cabin, I was miserable on this plane and could barely move when we arrived in Cabo due to the cramped leg area!

From Atlanta to Cabo I would have hoped on a plane that size I would have been able to breathe and wiggle my feet a little! The leg room in that plane is non existent and I am only 5”4’. And the air vent either wasn’t working very well or just could not blow air from the ceiling to the seat area as I was suffocating through the entire flight! And please don’t say I would have been more comfortable in first class because I cannot afford those rates and have always travelled Main Cabin without issues !

The pilots were good. Disappointing when planes don't have electrical ports

I liked the piloting of the aircraft. Very disappointed about lack of electrical ports. Also, although a short flight. there was enough time to hand out snacks to comfort + seats as was done for first class.

I had a wonderful experience flying with delta. The gentleman taking care of us on our flight was so nice, accommodating, and attentive. He always was smiling and giving pins to the kids which made me smile. The flight was quick too and without turbulence. Thank you for the great flying experience.

Delta is one of the best airlines I have flown

Made the Atlanta to Pittsburgh trip many times, with Delta no issues

I always fly with Delta. My friends tell me their horror stories of flying with other airlines. I just smile and say, “You should fly Delta”

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

All flights were on time and boarding was issue free

Terrible! The plane was old and you are required to connect your own device to their Wi-Fi rather than have entertainment options in the back of the seat in front of you. The Wi-Fi went out during the flight and there was only one plug for the devices every two seats. Three out of five surrounding my family did not work. The seats and spaces under them were so small I could not fit my backpack, which I’ve always brought on flights and fit before no problem. The crew were unpleasant and patronizing.

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Food was terrible Not many options Stewards dont care Delay

Water service would be great. The way they board is terrible. Slow passengers first😂😂 They need to smart up a bit

Our original business class flight was cancelled so we not only downgraded but we were also spread out across the plane not sitting together in separate middle seats. My poor kids were scared and couldn’t see me on the flight and the crew wasn’t sensitive to the situation and what the airlines did to us. Very dissatisfied with United airlines.

Crew were fine, drinks and snacks were as well but we were delayed for around 2 hrs which made our entry into Mexico delayed as well with the influx of arrivals at the same time. Sort of wasted our first day of vacation. We left Pittsburgh at 630am and did not arrive in Mexico until late dinner time.

The ride was good but no food ot entertainment hence, it was just over an hour flight.

There was a group of school age passengers that were very loud and unruly with their chaperones were no where to be found.

LATE LATE LATE!!! Plagued by late AA flights on this trip. Such a drag. This one was by far the worst.

WiFi connected but only let you go to the AA website, not even text messaging worked.

Too bad that first class seats do not recline significantly causing discomfort

I think the seats on some of their planes are uncomfortable. You can be ok on a short flight of two hours but no more than that. The delays, and also the refreshments on the plane were not enough.

Flight delayed over an over all day until it cancelled at 1:30am. Would not repeatedly delay that late. Offer hotel rooms and rebook early. Very difficult for families with small children

Not sure why JAL partnered with American Airlines because their service is no where near similar. Flight attendants were not friendly and didn’t smile. Food was horrible…

this is starting to seem like an american airlines standard. delayed flights and fake apologies… getting tired of it

Terrible boarding , Business class seats are sub standard. As usual crew will miss your food too

Just get Economy Plus for international flights, so worth it the extra room, bigger seats…

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

The guy with severe body odor sat next to me. For the whole duration of the flight it was a torture. The airline should have better policy on limiting people with bad body odor to board the flight. Passengers should not be the ones to endure bad odor for the whole duration of the flight. The airline should be e the one to ensure decent air quality for ever passenger.

Overall it was a miserable experience... I will never fly spirit for more than a 3 hour flight or overnight.

The boarding attendant was slightly rude when I asked about checking our stroller. Made me feel like I was bothering her.

My wife and I are both handicapped and at boarding they upgraded us to a seat closer to the front rather than all the way towards the back. Much appreciated.

Not much seat room, but that was unexpected. But the seat headrest was very uncomfortable.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries.

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Spirit canceled the flight in March and never notified me!

Seats suck, not enough room, overcrowded planes, hectic situation all together.

Pretty good. Would’ve been excellent if we would have left on time and the crew wasn’t late.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

They cancelled the flight then did nothing to help us rebook. It was awful - I won’t fly with them again

The process of buying the ticket and navigating all the hidden charges that Frontier throws at you was a terrible experience. The actual airport experience and flying was fine.

The truck that was refueling the plane drove away with the hose still connected to the plane and ripped part of the plane off with it

Not have to pay for every single item to take a flight. Seating and delays sucked.

Book cheap flights from Cleveland to Caribbean

Recent round-trip flight deals

5/14Tue
1 stop
14h 11mCLE-SJU
5/22Wed
nonstop
4h 51mSJU-CLE
$141
5/14Tue
2 stopsSpirit Airlines
23h 19mCLE-SJU
5/15Wed
2 stopsSpirit Airlines
11h 48mSJU-CLE
$151
5/14Tue
nonstopFrontier
4h 20mCLE-SJU
5/25Sat
nonstopFrontier
4h 51mSJU-CLE
$178
5/12Sun
1 stopAmerican Airlines
8h 47mCLE-SJU
5/16Thu
1 stopAmerican Airlines
6h 53mSJU-CLE
$187
5/11Sat
1 stopFrontier
16h 34mCLE-SJU
5/14Tue
nonstopFrontier
4h 32mSJU-CLE
$188
5/11Sat
2 stopsAmerican Airlines
9h 05mCLE-SJU
5/16Thu
2 stopsAmerican Airlines
10h 48mSJU-CLE
$252
5/11Sat
2 stopsUnited Airlines
11h 43mCLE-SJU
5/15Wed
1 stopUnited Airlines
11h 41mSJU-CLE
$298
9/5Thu
1 stopDelta
11h 09mCLE-SJU
9/9Mon
1 stopDelta
10h 10mSJU-CLE
$324
9/3Tue
1 stopDelta
7h 14mCLE-STT
9/10Tue
1 stopDelta
10h 08mSTT-CLE
$418
5/3Fri
1 stopUnited Airlines
7h 35mCLE-NAS
5/13Mon
1 stopUnited Airlines
18h 26mNAS-CLE
$684

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Recent one-way flight deals

5/15Wed
1 stopSpirit Airlines
12h 28mCLE-SJU
$39
5/15Wed
1 stopSpirit Airlines
12h 28mCLE-SJU
$46
5/14Tue
nonstopFrontier
4h 20mCLE-SJU
$81
5/14Tue
nonstopFrontier
4h 20mCLE-SJU
$89
5/12Sun
2 stopsAmerican Airlines
9h 18mCLE-SJU
$93
5/6Mon
1 stopAmerican Airlines
11h 38mCLE-SJU
$94
5/11Sat
2 stopsDelta
18h 20mCLE-AUA
$145
5/24Fri
1 stopUnited Airlines
22h 16mCLE-AUA
$236
5/11Sat
2 stopsDelta
17h 55mCLE-SDQ
$314
9/25Wed
3 stopsUnited Airlines
19h 47mCLE-SJU
$396

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Last minute flights from Cleveland to Caribbean

Last minute flight, train and bus deals

5/4Sat
multi-stop
7h 17mCLE-SJU
5/14Tue
multi-stop
27h 01mSJU-CLE
$202
5/5Sun
multi-stop
6h 19mCLE-SJU
5/11Sat
nonstop
4h 32mSJU-CLE
$205
5/2Thu
multi-stopFrontier
10h 50mCLE-SJU
5/12Sun
nonstopFrontier
4h 32mSJU-CLE
$208
5/1Wed
multi-stopFrontier
16h 33mCLE-SJU
5/10Fri
nonstopFrontier
4h 32mSJU-CLE
$209
5/5Sun
multi-stopSpirit Airlines
6h 19mCLE-SJU
5/8Wed
multi-stopSpirit Airlines
11h 48mSJU-CLE
$222
5/5Sun
multi-stopSpirit Airlines
6h 19mCLE-SJU
5/8Wed
multi-stopSpirit Airlines
28h 59mSJU-CLE
$227
5/4Sat
multi-stopAmerican Airlines
10h 35mCLE-SJU
5/6Mon
multi-stopAmerican Airlines
11h 22mSJU-CLE
$336
5/3Fri
multi-stopAmerican Airlines
8h 23mCLE-SJU
5/10Fri
multi-stopAmerican Airlines
11h 22mSJU-CLE
$341
5/2Thu
multi-stopUnited Airlines
7h 35mCLE-NAS
5/11Sat
multi-stopUnited Airlines
18h 26mNAS-CLE
$684
5/2Thu
multi-stopUnited Airlines
5h 38mCLE-NAS
5/11Sat
multi-stopUnited Airlines
6h 31mNAS-CLE
$687

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