$140 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 8/4. 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
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, Sep 16 - Sat, Sep 19
American Airlines Logo
6:27 am - 7:30 pm
SJU
-
CLE
13h 03m
2 stops
American Airlines Logo
4:31 pm - 9:24 am
CLE
-
SJU
16h 53m
2 stops
$238American Airlines
Thu, Aug 13 - Tue, Aug 18
Frontier Logo
6:00 am - 2:36 pm
SJU
-
CLE
8h 36m
1 stop
Frontier Logo
2:04 pm - 12:56 am
CLE
-
SJU
10h 52m
1 stop
$248Frontier
Tue, Aug 4 - Fri, Aug 14
Frontier Logo
6:00 am - 2:36 pm
SJU
-
CLE
8h 36m
1 stop
Frontier Logo
1:54 pm - 12:41 am
CLE
-
SJU
10h 47m
1 stop
$252Frontier
Mon, Sep 21 - Sat, Sep 26
Delta Logo
12:59 pm - 11:02 pm
MBJ
-
CLE
9h 03m
1 stop
Delta Logo
8:10 am - 3:34 pm
CLE
-
MBJ
8h 24m
1 stop
$357Delta
Sat, Sep 12 - Fri, Sep 18
United Airlines Logo
2:40 pm - 11:28 am
MBJ
-
CLE
19h 48m
1 stop
United Airlines Logo
4:07 pm - 11:43 am
CLE
-
MBJ
20h 36m
1 stop
$362United Airlines
Sat, Sep 12 - Fri, Sep 18
American Airlines Logo
5:16 pm - 9:15 am
MBJ
-
CLE
14h 59m
2 stops
American Airlines Logo
8:49 pm - 12:53 pm
CLE
-
MBJ
17h 04m
2 stops
$371American Airlines
Thu, Jul 9 - Wed, Jul 15
Southwest Logo
3:45 pm - 12:20 am
AUA
-
CLE
8h 35m
1 stop
Southwest Logo
1:35 pm - 12:45 pm
CLE
-
AUA
23h 10m
2 stops
$489Southwest
Wed, Jul 22 - Wed, Jul 29
Delta Logo
4:31 pm - 12:17 am
STT
-
CLE
7h 46m
1 stop
Delta Logo
8:05 am - 3:20 pm
CLE
-
STT
7h 15m
1 stop
$609Delta
Thu, Jul 9 - Wed, Jul 15
Southwest Logo
1:45 pm - 12:20 am
AUA
-
CLE
10h 35m
2 stops
Southwest Logo
1:35 pm - 12:45 pm
CLE
-
AUA
23h 10m
2 stops
$638Southwest
Thu, Jul 30 - Mon, Aug 3
United Airlines Logo
1:22 pm - 9:59 pm
STT
-
CLE
8h 37m
1 stop
United Airlines Logo
6:00 am - 12:20 pm
CLE
-
STT
6h 20m
1 stop
$804United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$140
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 4246 reviews
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

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.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

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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