$119 Find Cheap Flights from Caribbean Islands to Cleveland - Compare and Save

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 8/19. 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

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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

Wed, Aug 19 - Sat, Aug 22
American Airlines Logo
6:00 am - 11:50 pm
SJU
-
CLE
17h 50m
1 stop
American Airlines Logo
12:56 pm - 11:43 pm
CLE
-
SJU
10h 47m
1 stop
$238American Airlines
Wed, Aug 19 - Sat, Aug 22
Frontier Logo
6:00 am - 9:57 pm
SJU
-
CLE
15h 57m
1 stop
Frontier Logo
7:45 am - 3:58 pm
CLE
-
SJU
8h 13m
1 stop
$277Frontier
Wed, Aug 5 - Wed, Aug 26
Frontier Logo
6:00 am - 2:36 pm
SJU
-
CLE
8h 36m
1 stop
Frontier Logo
7:45 am - 3:58 pm
CLE
-
SJU
8h 13m
1 stop
$280Frontier
Mon, Aug 10 - Tue, Aug 18
Frontier Logo
7:10 am - 11:38 pm
SJU
-
CLE
16h 28m
1 stop
Frontier Logo
7:45 am - 3:58 pm
CLE
-
SJU
8h 13m
1 stop
$284Frontier
Fri, Jul 31 - Fri, Aug 21
United Airlines Logo
2:40 pm - 11:14 am
MBJ
-
CLE
19h 34m
1 stop
United Airlines Logo
6:27 pm - 1:30 pm
CLE
-
MBJ
20h 03m
1 stop
$404United Airlines
Sat, Aug 29 - Tue, Sep 15
Multiple Airlines Logo
3:35 pm - 11:12 pm
SDQ
-
CLE
7h 37m
1 stop
Multiple Airlines Logo
3:40 pm - 4:29 pm
CLE
-
SDQ
24h 49m
2 stops
$438Multiple Airlines
Sat, Aug 29 - Tue, Sep 15
Multiple Airlines Logo
9:38 am - 11:12 pm
PUJ
-
CLE
13h 34m
1 stop
Multiple Airlines Logo
8:10 am - 5:05 pm
CLE
-
PUJ
32h 55m
2 stops
$441Multiple Airlines
Fri, Jul 31 - Fri, Aug 21
Delta Logo
4:59 pm - 12:49 am
MBJ
-
CLE
6h 50m
1 stop
Delta Logo
7:05 am - 3:34 pm
CLE
-
MBJ
9h 29m
1 stop
$470Delta
Fri, Jul 3 - Sun, Jul 5
Southwest Logo
12:35 pm - 8:40 pm
MBJ
-
CLE
7h 05m
1 stop
Southwest Logo
6:35 am - 2:35 pm
CLE
-
MBJ
9h 00m
2 stops
$592Southwest
Wed, Sep 23 - Sat, Sep 26
United Airlines Logo
6:00 am - 9:51 pm
STI
-
CLE
15h 51m
1 stop
United Airlines Logo
12:25 pm - 10:52 pm
CLE
-
STI
10h 27m
1 stop
$615United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flight$119
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 13% 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 airlines flying 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.
7.4
United AirlinesOverall score based on 9830 reviews
7.7Boarding
6.6Food
7.1Entertainment
8.1Crew
7.3Comfort
Airline reviews

This planes staff was top tier. Everything went great and had a great flight home.

10.0 ExcellentKati, Jun 2026
DEN - DFW
Read more United Airlines reviews

This planes staff was top tier. Everything went great and had a great flight home.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

This was an overnight flight, and in the morning they did know coffee service. How you can throw passengers in a San Francisco airport at 5:40 a.m. in the morning and not giving them Coffee is a crime.

Our flight was delayed several Times due to mechanical issues. Although I understand this may happen at times, it was very inconvenient and we had to book a hotel for an overnight stay. We were traveling with my 3-yo grandson and waiting at the airport from noon until 6:30pm with no reassurance that our next rescheduled flight would depart, we had to decide what’s best for him. A day later, I found out that I may be able to demand compensation if my flight is delayed more than 4 hours. I will hav to read the fine print next time.

The pilot had to extend the flight time from san antonio to Houston to burn off fuel. This caused a lot of unnecessary stress since we had a tight connection to Aruba. And with no other flights going to Aruba we were worried about spending a night in Houston. We had to to run to our connection because of the flight crews mistake. Not happy.

Service was professional and quick. Premium economy seat was comfortable given the class

I'm a United 1K member and have ben for 10 years. The gate agent had no control over the boarding process and had us passengers queued for hours as delays were announced. On the plane, the overhead air nozzle was broken so col over was powering through on me and the passenger next to me. Not a great experience for a million miler on United. Feel free to contact me. Josh Smigel - DM426089

Like: departed and arrived on time. Unlike: Food options for purchase allways bad, 1 of 2 of the crew members not very friendly at all. Seats and leg room aweful. At this point I am thinking on switching to AA.

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

I missed my flight and had to buy new tickets Rome- Boston

Awfully rude American worker at door when we started boarding flight. Then, walk into a blazing hot airplane with no air conditioning until twenty minutes into the flight. Free entertainment was non existent! My husband, along with the fellow passenger in our row, and I could not get entertainment to work, no WIFI! Really?? Been flying American a long time. Was very disappointed.

Flight was delayed by 6 hours... the level of incompetence was truly astounding. I won't be flying American Airlines again. I don't care if AA is direct and there is a layover with another airline, I'll take the layover.

Leave on time. We waited on the plane for hour hours and it was hot and smelly

Check in was easy. Flights were smooth. Flight attendants were courteous and friendly.

Two hours delay, probably one hour because they didn’t bring catering and they had to bring water in board. There a change of aircraft. But delays galore at CLT so it must be a CLT and/or AA operation issue. The 1 hr additional delays because nobody could bring 2 packs of water sooner is probably the best example of this airline operates

Crew was nice, aircraft dated, entertainment same. Internet is expensive and terribly slow. Food pretty bad

Horrible experience. Food was ridiculous, insufficient, and not appetizing at all. They served sugary granola bar for breakfast. Furthermore, my bags were delayed and delivered damaged and American made it impossible to file for damages. Furthermore, the flights were delayed causing unnecessary stress given the connecting flights. It was awful experience, would never want to fly American.

My flight times changed 4 times since I originally booked the flight. The last time being the day of flight - a 2 hour delay. This meant instead of getting into IAH at 9:30p, I got in at 2:30a. This was very disappointing!!!

Flight was delayed 5 hours. Initial reason for delay was 'maintenance' - which makes sense. Then, the additional 2 hours continued to say it was maintenance - when I know EWR had a 2 hour delay. AA did not say that. Additionally, when boarding, there was only one agent at the counter for a long time - until another came to help. After boarding, we had to wait another 45 minutes due to 'no catering'. So while we waited for catering, AA continued to board additional passengers - which seemed odd - and raised questions about what really was going on. I sat in First Class. During the flight, the flight crew allowed a significant number of non-First Class passengers to use the front bathroom - which created a very crowded environment in First Class which was uncomfortable. This also delayed First Class passengers from using the bathroom. Overall, horrible experience.

My table was broken so it made it difficult to eat the food during the service. I was also informed that my luggage did not make it with me to Phoenix. I live two hours away so this makes it even more stressful to try and arrange a time for pick up

Traveling to a place near Cleveland?

Book flights to Cleveland if you plan to visit one of these locations
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Everything you need to know for your flight to Cleveland

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