$71 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 2/18. 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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Everything you should know

Cheapest round-trip
$145
Overall average: $294
Frontier
Thu 1/15Sun 1/18
SJU - CLE • 1 stop
Cheapest non-stop
$513
Frontier
Sun 2/8Sun 2/15
PUJ - CLE • Non-stop
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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

Thu, Jan 15 - Sun, Jan 18
Frontier Logo
6:00 am - 1:38 pm
SJU
-
CLE
8h 38m1 stop
Frontier Logo
3:45 pm - 1:20 am
CLE
-
SJU
8h 35m1 stop
$145Frontier
Sat, Feb 14 - Sat, Feb 21
Frontier Logo
7:05 am - 7:54 pm
SJU
-
CLE
13h 49m1 stop
Frontier Logo
6:29 pm - 12:54 am
CLE
-
SJU
29h 25m1 stop
$159Frontier
Thu, Jan 15 - Mon, Jan 19
Frontier Logo
6:00 am - 1:38 pm
SJU
-
CLE
8h 38m1 stop
Frontier Logo
5:30 am - 2:00 pm
CLE
-
SJU
7h 30m1 stop
$166Frontier
Tue, Feb 10 - Tue, Feb 17
Multiple Airlines Logo
5:47 pm - 7:43 pm
PUJ
-
CLE
26h 56m1 stop
Multiple Airlines Logo
7:04 pm - 4:36 pm
CLE
-
PUJ
20h 32m1 stop
$297Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
American Airlines Logo
5:59 pm - 10:30 am
AUA
-
CLE
17h 31m1 stop
American Airlines Logo
6:00 am - 4:50 pm
CLE
-
AUA
9h 50m2 stops
$303American Airlines
Tue, Feb 10 - Tue, Feb 17
Multiple Airlines Logo
5:47 pm - 7:43 pm
PUJ
-
CLE
26h 56m1 stop
Multiple Airlines Logo
8:46 pm - 4:36 pm
CLE
-
PUJ
18h 50m2 stops
$314Multiple Airlines
Tue, Feb 10 - Tue, Feb 17
American Airlines Logo
6:07 pm - 12:35 pm
PUJ
-
CLE
19h 28m2 stops
American Airlines Logo
7:44 pm - 1:41 pm
CLE
-
PUJ
16h 57m2 stops
$360American Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
2:55 pm - 4:54 pm
PUJ
-
CLE
26h 59m1 stop
United Airlines Logo
8:00 pm - 12:59 pm
CLE
-
PUJ
15h 59m1 stop
$368United Airlines
Tue, May 5 - Tue, Sep 8
Delta Logo
6:10 am - 11:39 pm
STI
-
CLE
17h 29m1 stop
Delta Logo
7:15 am - 7:28 pm
CLE
-
STI
12h 13m1 stop
$460Delta
Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
6:00 am - 1:18 pm
SDQ
-
CLE
8h 18m1 stop
United Airlines Logo
6:15 am - 3:06 pm
CLE
-
SDQ
7h 51m1 stop
$464United Airlines
Useful Info

Good to know

Low seasonSeptember
Cheapest flight$79
Best time to beat the crowds but there is an average 29% 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 4256 reviews
7.5Entertainment
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

10.0 ExcellentAnonymous, Dec 2025
DAL - CHS
Read more Southwest reviews

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Did not realize internet screen was hidden between seats and no info printed!!!!

I went to washroom twice and once there was no toilet seat cover and the other no toilet paper at all. I don't think it was ever replenished or checked before we boarded as it was very early on in the flight.

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Advertised fruit trays with cheese, but only snacks handed out!

The plant way delayed departing by 3 hours. It was an old airplane with broken seats and armrests. The bathroom made a hollering sound. A really crappy flight experience and travel day all around.

Premium economy is like the forgotten class. Aside from meal service never saw a flight attendant. Any additional beverages required going to the very back of the plane to request and there was rarely an attendant there. Seat leg / foot rest hardly elevates and not well suite for someone under 5’6. Bulky armrests

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

everything was pretty good. Houston airport is awful. Unnecessarily inefficient; people working there are rude. Badly run

United airlines has the best customer experience from booking to arrival. I always fly United airlines. The mileage program is excellent

They did the one thing that really matters - got to Chicago early.

I liked the snacks and the flight attendants were friendly.

The flight was delayed for 1:30 hours for maintenance issues. They should give more information about connecting flights. For a Business Cabin the Crew was mediocre.

Very turbulent trip made it pretty bearable, plus the lack of refreshments served and the lack of any air conditioning before takeoff which took an hour or more.

Flight was late - I was downgraded from first class to coach

Not good - outbound flight was delayed and missed my connection even though I got to the gate after running through the airport - the agent would not let me on because the door was closed (flight had not left). There was no notification from United - overall experience was very disappointing. Additionally, I was downgraded from first class to coach on the alternative flight

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

WiFi didn’t work the entire flight. Very disappointing. Minimal food and options - sadly the state of current affairs. All other aspects of the flight were fine.

Great flight - friendly and attentive team! Seats in coach were comfy, but a little cramped - but that is the case with all airlines ;)

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Not clean and was told I would get a great seat and it was not great at all

Good- no snacks on a 4+ hour flight is painful but more painful was the lack of WiFi.

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

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

Better than expected. Staff were friendly and nice on both flights.

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

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