$107 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 4/19. 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.

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

Fri, May 8 - Fri, May 15
Frontier Logo
11:00 am - 10:40 pm
SJU
-
CLE
11h 40m
1 stop
Frontier Logo
12:55 pm - 12:50 am
CLE
-
SJU
11h 55m
1 stop
$186Frontier
Sat, Apr 25 - Sat, May 2
Frontier Logo
8:00 am - 3:20 pm
SJU
-
CLE
7h 20m
1 stop
Frontier Logo
9:05 pm - 10:39 am
CLE
-
SJU
13h 34m
1 stop
$189Frontier
Fri, May 8 - Sun, May 17
American Airlines Logo
2:05 pm - 11:59 pm
STT
-
CLE
9h 54m
1 stop
American Airlines Logo
6:04 am - 4:15 pm
CLE
-
STT
10h 11m
1 stop
$270American Airlines
Tue, May 12 - Mon, Sep 7
Delta Logo
4:59 pm - 12:32 am
MBJ
-
CLE
6h 33m
1 stop
Delta Logo
6:00 am - 3:34 pm
CLE
-
MBJ
10h 34m
1 stop
$307Delta
Tue, May 12 - Mon, Sep 7
American Airlines Logo
12:25 pm - 9:33 pm
MBJ
-
CLE
8h 08m
1 stop
American Airlines Logo
6:45 am - 12:31 pm
CLE
-
MBJ
6h 46m
1 stop
$308American Airlines
Fri, May 8 - Fri, May 15
United Airlines Logo
4:12 pm - 11:59 pm
MBJ
-
CLE
6h 47m
1 stop
United Airlines Logo
3:06 pm - 3:10 pm
CLE
-
MBJ
25h 04m
1 stop
$312United Airlines
Thu, May 7 - Wed, Sep 9
Delta Logo
1:18 pm - 9:43 pm
MBJ
-
CLE
7h 25m
1 stop
Delta Logo
6:00 am - 1:04 pm
CLE
-
MBJ
8h 04m
1 stop
$317Delta
Thu, May 7 - Mon, May 11
United Airlines Logo
4:40 pm - 9:40 am
PUJ
-
CLE
17h 00m
1 stop
United Airlines Logo
6:00 am - 12:40 pm
CLE
-
PUJ
6h 40m
1 stop
$340United Airlines
Thu, May 7 - Thu, Sep 3
Multiple Airlines Logo
1:16 pm - 6:27 pm
MBJ
-
CLE
28h 11m
1 stop
Multiple Airlines Logo
10:00 am - 11:20 am
CLE
-
MBJ
26h 20m
1 stop
$351Multiple Airlines
Wed, Apr 8 - Mon, Apr 27
Multiple Airlines Logo
4:35 pm - 5:13 pm
STT
-
CLE
24h 38m
1 stop
Multiple Airlines Logo
7:00 am - 4:15 pm
CLE
-
STT
9h 15m
1 stop
$406Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$107
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 15% 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 4331 reviews
7.0Food
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
Airline reviews

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

6.0 GoodDavid, Mar 2026
RSW - BWI
Read more Southwest reviews

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Wonderful crew, great movie selection and good food. I prefer Airbus to Boeing, much more comfortable

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

I lost my plane and spend 5 hours at the airport arriving at Buffalo at 1 am taxis are very expensive at that time.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

we did a return flight from Paris CDG to SFO. This trip was much better than the departing flight SFO to CDG. The food was better quality, the crew was nicer, and the interior of the plane seemed cleaner.

They promise free wi-fi prior to boarding and then once on board you are informed you have to purchase wifi even after being a mileagePlus member.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

Awful. No counter attendants. No dinner offered due to delays.

Horrible service no Wi-Fi connection on both leg of the flight and they are refusing to fix bad service

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

We had excellent customer service despite the chaos at George Bush airport in Houston!

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Delays with no explanation. It could have been handled better.

The crew acted like they had never done this and kept barking passive aggressive orders at people. + the security line + the delay + sitting on the tarmac for 2 hours + none of the apps or signage updating with correct times

More inflight connection. And leg space is horrible. And the paying for baggage I'd ridiculous!!!

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

Our flight was canceled. I will never use Kayak nor Frontier for travel again. The entire experience was a headache.

Frontier.. nickel and dime add-ons. Flight late, on time, late again, last minute gate change, arrival gate required a shuttle to the terminal. They sure keep you guessing.. if you like a little chaos and airport anxiety, this is the airline for you!

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
Concord
Sheffield
Grafton
Valley City

Everything you need to know for your flight to Cleveland

Information on the airport you'll fly into in Cleveland