$64 Find Cheap Flights from Caribbean Islands 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 1/12. 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
$148
Overall average: $316
Frontier
Sat 1/24Mon 1/26
SJU - CLE • 1 stop
Cheapest non-stop
$425
Frontier
Wed 12/24Mon 12/29
SJU - CLE • Non-stop
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Flight Deals
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Flight Deals

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

Sat, Jan 24 - Mon, Jan 26
Frontier Logo
4:36 pm - 12:43 am
SJU
-
CLE
9h 07m1 stop
Frontier Logo
7:10 am - 3:12 pm
CLE
-
SJU
7h 02m1 stop
$148Frontier
Wed, Dec 24 - Wed, Jan 7
Frontier Logo
6:00 am - 5:50 pm
SJU
-
CLE
12h 50m1 stop
Frontier Logo
4:53 pm - 9:08 am
CLE
-
SJU
15h 15m1 stop
$158Frontier
Wed, Dec 24 - Thu, Jan 8
Frontier Logo
4:16 pm - 11:13 pm
SJU
-
CLE
7h 57m1 stop
Frontier Logo
7:24 pm - 2:50 am
CLE
-
SJU
6h 26m1 stop
$159Frontier
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
11:15 am - 6:03 pm
SJU
-
CLE
7h 48m1 stop
Multiple Airlines Logo
9:59 pm - 3:35 pm
CLE
-
SJU
16h 36m2 stops
$176Multiple Airlines
Mon, Jan 12 - Sun, Jan 18
Multiple Airlines Logo
4:40 pm - 11:11 pm
AUA
-
CLE
31h 31m2 stops
Multiple Airlines Logo
3:45 pm - 3:35 pm
CLE
-
AUA
22h 50m1 stop
$276Multiple Airlines
Thu, Jan 15 - Sun, Jan 18
United Airlines Logo
3:00 pm - 10:14 pm
AUA
-
CLE
8h 14m1 stop
United Airlines Logo
7:55 pm - 1:50 pm
CLE
-
AUA
16h 55m1 stop
$312United Airlines
Wed, Jan 28 - Wed, Feb 4
American Airlines Logo
4:50 pm - 10:00 am
AUA
-
CLE
18h 10m2 stops
American Airlines Logo
6:00 am - 2:00 pm
CLE
-
AUA
7h 00m1 stop
$316American Airlines
Fri, Feb 6 - Mon, Feb 9
United Airlines Logo
12:56 pm - 6:59 pm
PUJ
-
CLE
7h 03m1 stop
United Airlines Logo
6:15 am - 1:49 pm
CLE
-
PUJ
6h 34m1 stop
$356United Airlines
Mon, Jan 12 - Sun, Jan 18
American Airlines Logo
3:46 pm - 11:40 pm
AUA
-
CLE
8h 54m1 stop
American Airlines Logo
2:10 pm - 3:50 pm
CLE
-
AUA
24h 40m1 stop
$366American Airlines
Mon, Jan 26 - Fri, Jan 30
Delta Logo
6:39 am - 4:22 pm
STI
-
CLE
10h 43m1 stop
Delta Logo
12:33 pm - 8:34 pm
CLE
-
STI
7h 01m1 stop
$460Delta
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$64
Best time to beat the crowds but there is an average 39% 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 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 4 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.
7.9
DeltaOverall score based on 8008 reviews
8.5Crew
8.1Boarding
7.9Entertainment
7.3Food
7.9Comfort
Airline reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

6.0 GoodJeff, Dec 2025
JFK - MIA
Read more Delta reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

Movie selection is good. Crew did not understand mileage program and were no help. Sick later. Food?

Staff on board was excellent. Positive upbeat helpful- like it used to be.

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

For an expensive flight to another country, United has a lot of nerve serving pretzels and no meals (unless, of course, you want to buy something to eat). Unacceptable.

The food is terrible. The same pasta or chicken with bad taste and presentation

United have really come back. Airport and boarding process is clear and good, app and information also very good

The Sears in the 800s are not too good perfect Airbus why cant the new 737 fix that

Flight was delayed 8 times. We were sitting at the airport for 14 hours. We got 2 hours of sleep (if that) on what was not meant to be a red-eye.

It was probably one of the worst flights I’ve been on. The restrooms were never cleaned or stocked. The food was very subpar, and i usually enjoy airline food, so I was disappointed. It was just all around a bad experience. The only saving grace was the flight attendants.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

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.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

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