$148 Find Cheap Flights from Caribbean to Cleveland - Compare and Save

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 7/8. 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.
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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

Thu, Aug 6 - Mon, Sep 21
Frontier Logo
6:00 am - 2:36 pm
SJU
-
CLE
8h 36m
1 stop
Frontier Logo
3:40 pm - 11:57 pm
CLE
-
SJU
32h 17m
2 stops
$268Frontier
Sun, Aug 9 - Sun, Aug 23
Frontier Logo
7:10 am - 11:38 pm
SJU
-
CLE
16h 28m
1 stop
Frontier Logo
2:04 pm - 12:34 am
CLE
-
SJU
10h 30m
1 stop
$274Frontier
Fri, Aug 21 - Mon, Aug 31
American Airlines Logo
3:47 pm - 11:38 pm
SJU
-
CLE
7h 51m
1 stop
American Airlines Logo
4:54 pm - 11:59 pm
CLE
-
SJU
7h 05m
1 stop
$278American Airlines
Tue, Oct 6 - Mon, Oct 19
Multiple Airlines Logo
2:43 pm - 2:57 pm
PUJ
-
CLE
24h 14m
2 stops
Multiple Airlines Logo
9:19 pm - 4:31 pm
CLE
-
PUJ
19h 12m
1 stop
$401Multiple Airlines
Mon, Aug 3 - Sun, Aug 16
American Airlines Logo
6:20 am - 6:38 pm
KIN
-
CLE
11h 18m
1 stop
American Airlines Logo
6:15 am - 7:42 pm
CLE
-
KIN
14h 27m
1 stop
$402American Airlines
Tue, Oct 6 - Thu, Oct 15
Multiple Airlines Logo
2:43 pm - 2:57 pm
PUJ
-
CLE
24h 14m
2 stops
Multiple Airlines Logo
9:19 pm - 7:54 pm
CLE
-
PUJ
22h 35m
1 stop
$406Multiple Airlines
Thu, Dec 24 - Sun, Jan 3
Delta Logo
1:50 pm - 12:35 am
STT
-
CLE
11h 45m
1 stop
Delta Logo
6:00 am - 3:05 pm
CLE
-
STT
8h 05m
1 stop
$412Delta
Wed, Oct 7 - Sat, Oct 17
United Airlines Logo
4:40 pm - 9:07 am
PUJ
-
CLE
16h 27m
1 stop
United Airlines Logo
4:07 pm - 2:27 pm
CLE
-
PUJ
22h 20m
1 stop
$425United Airlines
Thu, Oct 22 - Sun, Oct 25
United Airlines Logo
3:35 pm - 11:59 pm
PUJ
-
CLE
8h 24m
1 stop
United Airlines Logo
6:00 am - 12:08 pm
CLE
-
PUJ
6h 08m
1 stop
$446United Airlines
Fri, Jul 31 - Fri, Aug 21
Delta Logo
4:59 pm - 12:49 am
MBJ
-
CLE
6h 50m
1 stop
Delta Logo
7:05 am - 3:34 pm
CLE
-
MBJ
9h 29m
1 stop
$480Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$148
Best time to beat the crowds with an average 20% drop in price.
Most popular time to fly and prices are also 5% 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.
7.9
SouthwestOverall score based on 4250 reviews
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
8.1Boarding
Airline reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Other than a bit of a delay, everything was good. Again, the boarding process and picking seats is the only thing I don't enjoy.

Short flight with plenty of open seats. Drinks and snacks were still provided even on such a short flight. <1 hr

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

My experience with Southwest as a whole was good but coming out of Cancun to Chicago it was terrible. Not only was it a language barrier with customer service we stood there to ask questions and they act like they didn't even see you. So the first come approach is not all that great anymore.

Always a great experience. Crew is great at communicating things during flight

very disappointed by plane having no power outlets for our electronics

I kept getting h notifications that the flight was delayed. At the airport it was only 2 mins delay. Very confusing. No WiFi on the plan. Snacks very salty. No alternative

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

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.

Boarding and crew were fantastic, but I paid for a window seat with no window. Seat 11D on a CRJ-900 apparently does not have a window. Lesson learned.

The gate agent was most helpful in getting me on to fly standby. I greatly appreciate it.

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Although the flight left late, we arrived early. It was one of the quickest boarding and off boarding experiences I’ve had. It was kind of annoying the only drinks they had were water, coffee, and tea. The flight was very smooth, temperature was just right, and flight attendants were friendly.

Delayed in taking off because no flight crew. The in seat entertainment was working properly.

The WiFi has been awful on my last few Delta Air Lines flights.

Great - This was the last flight before hurricane closures and did a quick turnaround to get the plane heading north. Much appreciated.

The Gate Attendant @ Gate B36 was rude The flight was good but the entertainment system was not functioning as expected. The snacks were ok but could be better The flight crew was excellent.

The airline was fine, but I did want to share about Kayak's error through Underpricer. The original booking was purchased with ANA, and Kayak booked it with United. This is a mistake that should not be happening, since the price I paid was with ANA and that was my preference. I appreciate the efforts done to make this right by paying for the seat preference, but sitting in the back of the airplane under economy is not enough to make this error right. ANA Airlines was the experience I wanted considering this was a life time experience that my family and I wanted to have as part of our Japanese experience. Please work on your affiliation with Underpricer to make the right bookings that the customer pays for. In my situation, I could of paid less for a United ticket versus my original payment with ANA Airlines.

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Really hard landing... as in slammed into the runway then hit the brakes really hard ...

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

United is today and old, the planes, the staff, the business processes. Yet they expect premium prices for a less than average flight experience. I should have remembered to stay away from them and will remember to stay away from them in the future since I'm traveling a lot again. In a nutshell, they suck eggs.

The flight was clean and on schedule, but connections could have been better

Seat horribly lacking in lumbar support. Bluetooth earphone connection Jair wouldn’t work. Food options were quite tasty and staff was professional and efficient as well as welcoming.

You can’t checking with no carry on bag, the entertainment was awesome and the crew very friendly and polite🫶

Fine. Nothing to write home about. The plane left on time, and arrived on time.

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

After changing the departure gate 5 times making us mo e from one side of the airport to the other and then back the flight was delayed nearly 2 hours. The male flight attendant had a bad attitude with the guest being condescending, disrespectful with people who were already on edge.

American continues to decline in their customer service and its beyond disappointing.

Flight was delayed and after being in the airport for like seven hours, it was canceled.

Charlotte NC agents were great and ended up with decent seats after having to switch flights amidst Hurricane situation. CMH was a different story. Doors to flight closed 15 minutes before departure so we nearly were left behind. Flight crew were OK but nothing to brag about for sure

The one gate agent was very abrupt and rude. Not a good look for American for the day

The plane was very clean. The crew was excellent. The flight was delayed slightly but other than that no issues.

Experience was bad. 3.5 hour delay for a 2.5 hour trip. There was no r Transparency about the reason for the delay and it was done 30 mins at a time.

Flight was delayed, I tried to leave 2days earlier was told to report to airport for standby only to be turned away after paying for an Uber both way from Little Elm TX.

Flight got delayed for 5 hours no good explanation was offered ;(

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

Four and a half hour delay in total. What frustrates me most is the poor communication and disorganization.

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

The flight was canceled, then delayed twice, we were moved gates twice. Short staff at the counter and check in. We waited for our flight 9 hours. Will never use Frontier ever again, or Spirit.

It's Frontier: low-frills but boarding first because I paid for a carry-on was an unexpected perk, and the fact that it was direct and fast makes up for the lack of amenities.

There was only room for a quarter of the passengers to sit at the gate at MCO. The gate attendant allowed people who did not require assistance to board early before they realized and started to turn people back. The flight was extremely uncomfortable due to pressure. My ears, eyes, sinuses and joints were very painful the whole flight. My sister also complained about her ears and sinuses as well as joints and while deplaning I heard several other passengers complain about the same issues. I’ve never felt that much discomfort flying before and I’ve been doing it for over 40 years.

Got to where I needed to be safely. Thank you!

Even though my personal item fit into the testing compartment they had, the agent charged me for the bag and threatened to not let me board if I didn’t pay. He was doing this with everyone that was boarding, everyone was so pises. Never flying Frontier again

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