$146 Find Cheap Flights from Caribbean Islands 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 9/30. 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 Islands to Cleveland

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands 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 Islands to Cleveland

Wed, Oct 14 - Wed, Oct 28
Frontier Logo
9:49 pm - 9:02 am
SJU
-
CLE
11h 13m
1 stop
Frontier Logo
8:25 am - 3:25 pm
CLE
-
SJU
7h 00m
1 stop
$266Frontier
Wed, Sep 23 - Tue, Sep 29
Frontier Logo
3:08 am - 7:03 pm
SJU
-
CLE
15h 55m
1 stop
Frontier Logo
9:10 pm - 3:17 pm
CLE
-
SJU
18h 07m
1 stop
$267Frontier
Thu, Aug 13 - Mon, Aug 17
Multiple Airlines Logo
6:00 am - 2:36 pm
SJU
-
CLE
8h 36m
1 stop
Multiple Airlines Logo
6:33 pm - 4:11 pm
CLE
-
SJU
45h 38m
2 stops
$321Multiple Airlines
Wed, Sep 9 - Sat, Sep 12
Multiple Airlines Logo
8:45 am - 7:47 pm
SJU
-
CLE
11h 02m
2 stops
Multiple Airlines Logo
7:45 am - 5:03 pm
CLE
-
SJU
9h 18m
1 stop
$335Multiple Airlines
Wed, Sep 23 - Thu, Oct 1
American Airlines Logo
11:51 am - 11:42 pm
SJU
-
CLE
11h 51m
2 stops
American Airlines Logo
6:19 am - 3:40 pm
CLE
-
SJU
9h 21m
1 stop
$364American Airlines
Wed, Sep 23 - Thu, Oct 1
American Airlines Logo
11:51 am - 11:42 pm
SJU
-
CLE
11h 51m
2 stops
American Airlines Logo
6:00 am - 3:40 pm
CLE
-
SJU
9h 40m
2 stops
$364American Airlines
Thu, Aug 27 - Sat, Sep 19
United Airlines Logo
1:00 am - 1:09 pm
SJU
-
CLE
12h 09m
2 stops
United Airlines Logo
6:00 am - 12:34 pm
CLE
-
SJU
6h 34m
1 stop
$364United Airlines
Tue, Sep 15 - Thu, Sep 24
United Airlines Logo
1:00 am - 1:09 pm
SJU
-
CLE
12h 09m
2 stops
United Airlines Logo
7:00 am - 1:45 pm
CLE
-
SJU
6h 45m
1 stop
$364United Airlines
Thu, Sep 24 - Tue, Sep 29
Southwest Logo
6:30 am - 4:45 pm
SJU
-
CLE
10h 15m
2 stops
Southwest Logo
6:25 am - 4:25 pm
CLE
-
SJU
10h 00m
2 stops
$364Southwest
Fri, Sep 11 - Tue, Sep 15
Southwest Logo
6:30 am - 4:45 pm
SJU
-
CLE
10h 15m
2 stops
Southwest Logo
11:40 am - 9:00 pm
CLE
-
SJU
9h 20m
2 stops
$364Southwest
Useful Info

Good to know

Low season

January

Cheapest flight

$146
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from San Juan Airport to Cleveland

FAQs for booking flights from Caribbean Islands to Cleveland

  • How does KAYAK find such low prices on flights from Caribbean Islands 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 Islands to Cleveland.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to Cleveland?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Cleveland from Caribbean Islands 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 Islands 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 Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean Islands to Cleveland

 
Need help choosing which airline to fly with from Caribbean Islands 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.
7.4
United AirlinesOverall score based on 10063 reviews
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
6.7Food
Airline reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

4.0 OkayN, Jul 2026
PHL - ORD
Read more United Airlines reviews

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

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🫶

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

The boarding crew was very helpful with a little special problem I had. The inflight crew - so-so.

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.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight was delayed. But my finances flight with JetBlue a week before same route was extra delayed and then cancelled at 2am when his flight was suppose to take off at 7pm was never provided a hotel or anything. Came back to airport and his rescheduled flight was cancelled again for 2 days later. Was told since it was a weather issue they don’t do refunds. But that’s a lie because I booked him on another airline at the same time and they were able to take off perfectly fine

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

Plane was delayed multiple times. I would like to request a refund. Was due to arrive Thursday evening ended up arriving Friday morning.

The seats were roomier than other airplanes I’ve been on.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

Checking-in in Barbados was excellent, connecting in JFK to JAX was a nightmare, had to wait over 1 hour and 20 minutes to receive my check bag. After receiving my checked bag and going to the gate to check in for my flight to Jax the crew there had no clue. They first told me that I had missed the flight and had to rebooked.. after trying to speak with JetBlue reservations (without luck) I was asked to leave my Phone number for a recall, I did so and my call was returned after 15 hours. I finally looked at the information board and saw the flight that I was originally scheduled for was still at the gate. I alerted an JetBlue employee of my findings and was told to rush to the gate and see if I could still board. The agent at the boarding gate apparently was having a very bad day, after lecturing me on how late I was (which was not a fault of mine) let me on the flight. A VERY BAD EXPERIENCE. I will NEVER fly JetBlue ever in my life again.

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

The flight kept getting delayed, but the ground crew did not communicate well to the passengers in the terminal. First, we were told that it was an engine issue. That was understandable. We asked, after the third delay, if it would be canceled; they reassured us that that would not happen because a new plane was on its way from Washington DC. Four hours later, that is exactly what happened. No announcement was made only people who had the JetBlue app learned of the cancellation. They rebooked us on a flight that would get into our destination 36 hours after our original time I had to spend an exorbitant amount of money to book an additional flight with a different airline, the following morning in order to make it to my conference in time. Not to mention the fact that by the time I discovered the cancellation on the departures board, it was too late for me to receive a refund on my lodging in the destination city for that night. Because I had booked with KAYAK, I did not receive any JetBlue email with rebooking information. This is what the information information desk kept telling everyone who inquired about a rebooking. This was my first time flying with JetBlue. Needless to say, after extremely poor communication andover $1000 of additional expense later, I will not be flying with them again.

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