$112 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 4/14. 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

Sat, May 30 - Tue, Jun 2
Frontier Logo
4:45 pm - 12:38 am
SJU
-
CLE
7h 53m
1 stop
Frontier Logo
3:42 pm - 4:49 am
CLE
-
SJU
13h 07m
1 stop
$192Frontier
Wed, May 27 - Sat, May 30
Frontier Logo
6:00 am - 2:42 pm
SJU
-
CLE
8h 42m
1 stop
Frontier Logo
4:01 pm - 11:58 pm
CLE
-
SJU
7h 57m
1 stop
$210Frontier
Fri, May 8 - Fri, May 15
American Airlines Logo
5:05 pm - 11:59 pm
STT
-
CLE
6h 54m
1 stop
American Airlines Logo
6:49 pm - 1:15 pm
CLE
-
STT
18h 26m
2 stops
$270American Airlines
Thu, Apr 2 - Mon, Apr 6
American Airlines Logo
4:42 pm - 9:01 am
STT
-
CLE
16h 19m
1 stop
American Airlines Logo
6:22 pm - 11:35 am
CLE
-
STT
17h 13m
1 stop
$275American Airlines
Fri, May 8 - Sun, May 10
United Airlines Logo
2:10 pm - 10:44 pm
STT
-
CLE
8h 34m
1 stop
United Airlines Logo
6:00 am - 12:20 pm
CLE
-
STT
6h 20m
1 stop
$290United Airlines
Fri, May 1 - Fri, May 8
Delta Logo
2:10 pm - 11:05 pm
MBJ
-
CLE
7h 55m
1 stop
Delta Logo
8:05 am - 3:34 pm
CLE
-
MBJ
8h 29m
1 stop
$307Delta
Thu, Apr 16 - Thu, Apr 23
United Airlines Logo
1:52 pm - 1:21 am
MBJ
-
CLE
10h 29m
1 stop
United Airlines Logo
3:08 pm - 3:10 pm
CLE
-
MBJ
25h 02m
1 stop
$312United Airlines
Tue, May 12 - Sat, Sep 12
Delta Logo
4:59 pm - 9:17 am
MBJ
-
CLE
15h 18m
1 stop
Delta Logo
6:00 am - 3:34 pm
CLE
-
MBJ
10h 34m
1 stop
$353Delta
Fri, Apr 17 - Fri, Apr 24
Multiple Airlines Logo
10:49 am - 11:59 pm
STT
-
CLE
13h 10m
1 stop
Multiple Airlines Logo
5:00 pm - 11:30 am
CLE
-
STT
18h 30m
2 stops
$392Multiple Airlines
Fri, Apr 17 - Thu, Apr 30
Multiple Airlines Logo
2:35 pm - 11:55 pm
SDQ
-
CLE
9h 20m
1 stop
Multiple Airlines Logo
3:44 pm - 4:29 pm
CLE
-
SDQ
24h 45m
2 stops
$399Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$112
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 4320 reviews
8.1Boarding
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
Airline reviews

Boarding was easy. The seats are small and fairly uncomfortable

8.0 ExcellentNicole, Mar 2026
LGB - OAK
Read more Southwest reviews

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

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

No pilots so we were two hours late taking off and then no gate agents when we arrived in Salt Lake.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Hopped on time for the flight only to get deplaned and delayed another 2.5 hours.

Terrible experience! delay 2 time and say i dont have ticket

Both my flight where delayed Had 25min to make it to my transfer flight

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

Everything was on time and service on the flight was great!

The boarding in Buenos Aires (at the on ramp) was not great. They had to check every carry on. Not a United problem but was a Buenos Aires problem.

Staff and aircraft were good. However, weather in Houston lee to a ground stop. We were looking at circling behind three other planes until the stop was lifted. Pilot said we didn’t have enough fuel for that. So we flew on to New Orleans as the closest port with immigration and customs staff. Landed there and sat in the plane for two hours plus while staff was sorted. Turned away by ICE. Waited for pilots to be switched out, but after they were approved by ICE. Then had to wait to get a runway because so many planes were ahead of us. Finally took off and flew back to Houston. We all missed our connecting flights because it took too long. Hotel voucher from United was only a link to booking site. Total BS. Finally got a flight out the next day after a night without sleep because all the Houston hotels were booked by rodeo and spring break crowds.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

Really good. I accidentally left my duffel on the plane and the reps were so friendly in retrieving it.

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

As a first class customer, there was no power the entire flight which limited my ability to work. I find this unacceptable. The first 11 rows on the left side of the plan were out. I was only offered the option to charge my phone which was not the issue because my laptop was out of power. I asked if there was anything that can be done for me, and the answer was, "no". I was not offered any type of compensation for this AA problem which caused me unnecessary stress due to inability to address business issues on an already challenging travel day. Flight attendants tried to reset the power once but that was the extent of their support. Very disappointing for the lack of expected services on a flight. Please contact me with customer focused response to this complaint.

We changed our flight because of weather. Unfortunately we were on hold for over an hour, but since we were 5 people who all booked individually, we felt more comfortable doing it with an agent. It all worked out in the end.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

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.

Easy boarding. Rows are smaller but that may be an older and bigger me now :)

It would have been nice if American tried to care.

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!

This is my second time flying with Frontier. My current experience was very favorable. The staff from the gate to the plane was friendly, warm and professional. The food options lacked in my opinion. This area needs some attention in my opinion.

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
Sheffield
Concord
Grafton
Valley City

Everything you need to know for your flight to Cleveland

Information on the airport you'll fly into in Cleveland