$89 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 4/7. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Cleveland

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$178
Overall average: $217
Frontier
Sat 2/14Sat 2/21
SJU - CLE • 1 stop
Cheapest non-stop
$503
Frontier
Thu 2/19Thu 5/14
PUJ - CLE • Non-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Cleveland!
Flight Deals
Useful Info
Flight Deals

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

Sat, Feb 14 - Sat, Feb 21
Frontier Logo
1:52 pm - 11:09 pm
SJU
-
CLE
10h 17m
1 stop
Frontier Logo
6:29 pm - 12:54 am
CLE
-
SJU
29h 25m
1 stop
$178Frontier
Wed, Feb 4 - Sat, Feb 7
Frontier Logo
8:00 am - 2:39 pm
SJU
-
CLE
7h 39m
1 stop
Frontier Logo
8:00 am - 3:26 pm
CLE
-
SJU
6h 26m
1 stop
$180Frontier
Thu, Feb 5 - Sun, Feb 8
Multiple Airlines Logo
8:00 am - 4:40 pm
SJU
-
CLE
9h 40m
1 stop
Multiple Airlines Logo
3:10 pm - 6:58 pm
CLE
-
SJU
26h 48m
1 stop
$212Multiple Airlines
Wed, Feb 4 - Wed, Mar 4
Multiple Airlines Logo
3:32 pm - 10:59 pm
SDQ
-
CLE
8h 27m
1 stop
Multiple Airlines Logo
7:04 pm - 2:20 pm
CLE
-
SDQ
18h 16m
1 stop
$305Multiple Airlines
Thu, Feb 19 - Thu, May 14
United Airlines Logo
2:55 pm - 1:10 pm
PUJ
-
CLE
23h 15m
1 stop
United Airlines Logo
9:00 am - 3:12 pm
CLE
-
PUJ
30h 12m
1 stop
$349United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
12:56 pm - 9:50 am
PUJ
-
CLE
21h 54m
1 stop
United Airlines Logo
8:00 pm - 12:59 pm
CLE
-
PUJ
15h 59m
1 stop
$388United Airlines
Thu, Feb 19 - Thu, May 14
American Airlines Logo
5:41 pm - 12:10 pm
PUJ
-
CLE
19h 29m
1 stop
American Airlines Logo
6:49 pm - 10:50 am
CLE
-
PUJ
16h 01m
2 stops
$424American Airlines
Wed, May 6 - Thu, May 14
American Airlines Logo
11:27 am - 11:36 pm
STT
-
CLE
12h 09m
1 stop
American Airlines Logo
6:49 pm - 1:05 pm
CLE
-
STT
18h 16m
2 stops
$466American Airlines
Wed, May 6 - Thu, May 14
Delta Logo
1:15 pm - 10:40 pm
STT
-
CLE
9h 25m
1 stop
Delta Logo
6:00 am - 3:21 pm
CLE
-
STT
9h 21m
1 stop
$470Delta
Fri, May 15 - Mon, Sep 7
Delta Logo
6:10 am - 11:44 pm
STI
-
CLE
17h 34m
2 stops
Delta Logo
7:15 am - 7:28 pm
CLE
-
STI
12h 13m
1 stop
$484Delta
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$89
Best time to beat the crowds but there is an average 28% increase in price.
Most popular time to fly and prices are also 12% 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 4266 reviews
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
8.1Boarding
Airline reviews

Great flight but super high price. Glad it was a business trip and not personal

10.0 ExcellentPieter, Jan 2026
LGB - DAL
Read more Southwest reviews

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The flight crew was extremely rude and especially not helpful when our flight was delayed.

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

My requested wheelchair never appeared. So many entertainment choices yet, I found little of interest and no internet option to search on my own. Both were minor issues.

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Unfortunately weather delayed our flight waiting for our plane to arrive and due to a little snow time was needed to deice the plane so departure was very delayed and I missed the connecting flight

Mean flight attendant. I wanted to reuse my plastic cup, but he (Matthew) said he can't for safety. I then said "I don't want water then" and he poured me a glass. I hope Matthew gets herpes and spends the rest of his life poor, lonely, and homeless.

Very good. Because of the delays with my previous flight, I missed my connection, but I was able to book another flight through the United app easily.

It was great. There were some issues prior to takeoff. The weather was poor so we had to go through deicing, and we were delayed a bit by the pilots' concern about one of the engines, but that's aviation. The pilots handled everything with aplomb, and kept us apprised

Reliable, nice crew, I fly often on that flight and I like it all.

I wish there were outlets to charge my iPhone. The crew was great; we had a female pilot who was great with explaining what was happening and delays,

The seats were comfortable and we had leg room. Great entertainment.

The flight crew where really good. Better then the crew from BNE to SFO

Delayed, toilets did not flush, pilot parked to far away from Gate

Was happy we finally got upgraded in 1st class. The seat getting old. The cushiness need some improvement.

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

Could we please end the loud announcements about credit card offers on your flights? We are trying to sleep, work, watch videos, etc. and if we need a credit card, we will ask for one. Flying is already not what it used to be.

I would like the crew to talk LESS over the PA and specifically about credit card offers. I am trying to work, sleep, watch a movie and the PA was booming about a credit card offer. Could we go back to the days when the customer was more important than selling a credit card?

No enough space plus only allowing one laggage instead of two like other airlines.

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

When I got to the waiting area, it was full but when the time came to board, rgete was no plane. The women where you would show your ticket, gave the news saying there was a maintenance problem and that it be an extra half hour wait. We never did see the plane but ultimately, Noone ever saw the plane because there was a fire on one engine. Needless to say, the wait time before it was announced what really happened, was a few hours. Many, many missed their plane transfer because they entered their first train. Also, the electronic info panels up on the different wall for all to see the status of each flight, never stated anything having to do with the long, long hold up. Many people had major problems because they had to swith planes during their trip and that never happened...

Good for a budget airline! It was easy to get on, staff was really nice. Can’t say anything about the food or entertainment because it wasn’t available, which is fine.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

It was costly and difficult to check in. $85 to take a small suitcase with me, carry on or checked and $75 on the return trip, Plus $25 if I didn't check my self in check in $25, because I couldn't do it on the kiosk. Small very uncomfortable seats, waited on the runway for near an hour each way. It was my worst flight to date.

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

A 630departure flight Delayed 6hours! They changed my gate, I moved to the new gate. Had our flight on the screen for 12noon departure. I go get above to eat, check screen again and the flight was gone, no notice no announcement, nothing!! They sent my bag on the flight I wasn’t on, got it back to me 3days later. Thank goodness they did refund my money but I will NEVER fly them again.

Due to weather, my flight was delayed, further delayed, then canceled. I eventually got through to a support person who helped me find a different route out of MSP, but to get to DIA, they didn't want to, but eventually did help with the connection ticket purchase. But even this replacement flight was delayed time and time again, and I would have missed my connecting flights and I didn't want to get stuck in a layover city, so after 12 hours at the airport with two young boys who were very tired, we just cancelled our plans and spent the week at home, instead of Nana's.

Plane and crew on board were fine. Everything else was terrible.

The third party booking with cheapflightsfares was awful. Kayak should NOT partner with them. They sold me a bundle including seat selection and carry-on, but did not book the carry-ons with Frontier, so I’m out of pocket for $414 more while I await resolution.

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
Beachwood
Independence
Mentor
Kent
North Olmsted
Huron
Streetsboro
Medina
Willoughby
Kelleys Island
Cleveland Heights
Orange
Sheffield
Concord
Grafton
Valley City

Everything you need to know for your flight to Cleveland

Information on the airport you'll fly into in Cleveland