$101 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 5/23. 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

Thu, May 28 - Mon, Jun 1
Frontier Logo
6:00 am - 1:09 pm
SJU
-
CLE
7h 09m
1 stop
Frontier Logo
9:57 pm - 1:15 pm
CLE
-
SJU
15h 18m
1 stop
$192Frontier
Fri, May 15 - Tue, May 19
Frontier Logo
8:59 am - 8:52 pm
SJU
-
CLE
11h 53m
1 stop
Frontier Logo
6:30 am - 2:08 am
CLE
-
SJU
19h 38m
1 stop
$194Frontier
Thu, May 14 - Wed, Aug 26
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
$310Delta
Fri, May 15 - Fri, Aug 28
American Airlines Logo
12:56 pm - 11:59 pm
MBJ
-
CLE
10h 03m
1 stop
American Airlines Logo
6:05 am - 1:58 pm
CLE
-
MBJ
8h 53m
1 stop
$316American Airlines
Fri, May 29 - Sat, Sep 12
American Airlines Logo
5:17 pm - 10:51 am
MBJ
-
CLE
16h 34m
2 stops
American Airlines Logo
7:06 pm - 9:10 am
CLE
-
MBJ
15h 04m
2 stops
$321American Airlines
Thu, May 14 - Sat, Aug 29
Delta Logo
2:21 pm - 12:48 am
MBJ
-
CLE
9h 27m
1 stop
Delta Logo
6:00 am - 3:34 pm
CLE
-
MBJ
10h 34m
1 stop
$331Delta
Fri, Jul 31 - Sat, Aug 15
United Airlines Logo
4:12 pm - 11:44 pm
MBJ
-
CLE
6h 32m
1 stop
United Airlines Logo
7:55 pm - 3:10 pm
CLE
-
MBJ
20h 15m
1 stop
$383United Airlines
Fri, Jul 31 - Sun, Aug 16
United Airlines Logo
4:12 pm - 11:44 pm
MBJ
-
CLE
6h 32m
1 stop
United Airlines Logo
6:00 am - 3:10 pm
CLE
-
MBJ
10h 10m
1 stop
$387United Airlines
Mon, Jun 8 - Tue, Jun 16
Multiple Airlines Logo
12:41 pm - 7:57 am
SDQ
-
CLE
19h 16m
2 stops
Multiple Airlines Logo
4:36 pm - 4:29 pm
CLE
-
SDQ
23h 53m
1 stop
$395Multiple Airlines
Tue, May 12 - Fri, Aug 14
Multiple Airlines Logo
9:25 am - 1:09 pm
PUJ
-
CLE
27h 44m
1 stop
Multiple Airlines Logo
6:45 am - 2:34 pm
CLE
-
PUJ
7h 49m
1 stop
$398Multiple Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$104
Best time to beat the crowds with an average 14% drop 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 8465 reviews
8.5Crew
7.8Entertainment
8.1Boarding
7.9Comfort
7.2Food
Airline reviews

Round trip flight to Canada and back to the US was smooth and efficient.

8.0 ExcellentBrent, Apr 2026
YWG - MSP
Read more Delta reviews

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

My business class seat was inoperable and unable to recline for 10 hour flight.

Flew steerage class. Short on leg room unless you pay more. No window unless you pay more. Etc. United is trying to squeeze every cent from you. It doesn’t make for any loyalty.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

Outstanding service, great food, friendly & efficient crew, safe & comfortable flight

Staff were not attentive, wifi did not work, cut my head in the bathroom due to the position of the soap on the sink, had blood running down my face, told staff, they had no expression no sympathy, didn't even say "sorry", they said "oh we will have a look at that" about 10 mins later the purser brought me a bandaid, still no sorry.... Shocking

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

Poor... food was horrible, boarding very slow, service on board mediocre

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

They didn’t offer a water, even after I asked

Zero issues with this flight. Crew was outstanding and flight was super. Plane was clean and fine. The seats need more padding and water should be provided without cost. I recognize it's Frontier but there are some things that should still be part of the flight. But still very satisfied with the experience and quality.

They switched our terminal 3 times and we were delayed for four plus hours!!!

It was an early flight and most people napped/slept and the crew let us which was nice.

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!!

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
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Concord
Sheffield
Grafton
Valley City

Everything you need to know for your flight to Cleveland

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