$88 Find Cheap Flights from Cleveland to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Cleveland to Caribbean departing on 10/27. 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

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Cheap Flights from Cleveland to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$319
Santo Domingo
Santo Domingo1 stop$337
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad1 stop$347
Nassau
Nassau2 stops$457
Kingston
Kingston2 stops$465
Simpson Bay
Simpson Bay1 stop$408
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$508
Bridgetown
Bridgetown1 stop$471
George Town
George Town1 stop$505
Willemstad
Willemstad1 stop$540
St. John's
St. John's2 stops$657
Puerto Plata
Puerto Plata1 stop$477
Aguadilla
Aguadilla1 stop$234
Punta Cana
Punta Cana1 stop$319
Santo Domingo
Santo Domingo1 stop$337
Montego Bay
Montego Bay1 stop$351
Oranjestad
Oranjestad1 stop$347
Nassau
Nassau2 stops$457
Kingston
Kingston2 stops$465
Simpson Bay
Simpson Bay1 stop$408
Providenciales
Providenciales1 stop$439
Port of Spain
Port of Spain1 stop$508
Bridgetown
Bridgetown1 stop$471
George Town
George Town1 stop$505
Willemstad
Willemstad1 stop$540
St. John's
St. John's2 stops$657
Puerto Plata
Puerto Plata1 stop$477
Aguadilla
Aguadilla1 stop$234

Book Cheap Cleveland to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Cleveland to Caribbean 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 Cleveland to Caribbean

Fri, Oct 24 - Tue, Oct 28
American Airlines Logo
12:48 pm - 11:59 pmCLE-SJU
11h 11m1 stop
American Airlines Logo
1:50 pm - 12:15 amSJU-CLE
10h 25m1 stop
$175American Airlines
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Sun, Sep 7 - Thu, Sep 11
United Airlines Logo
7:00 am - 1:45 pmCLE-SJU
6h 45m1 stop
United Airlines Logo
1:05 am - 9:23 amSJU-CLE
8h 18m1 stop
$187United Airlines
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Sat, Oct 4 - Sat, Oct 11
Delta Logo
5:30 am - 12:59 pmCLE-SJU
7h 29m1 stop
Delta Logo
7:15 am - 5:18 pmSJU-CLE
10h 03m1 stop
$215Delta
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Mon, Sep 1 - Fri, Sep 26
Delta Logo
5:30 am - 1:10 pmCLE-SJU
7h 40m1 stop
Delta Logo
5:41 pm - 12:39 amSJU-CLE
6h 58m1 stop
$225Delta
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Sat, Sep 13 - Thu, Sep 18
Spirit Airlines Logo
4:45 pm - 9:44 amCLE-STT
16h 59m1 stop
Spirit Airlines Logo
10:49 am - 6:56 pmSTT-CLE
8h 07m1 stop
$232Spirit Airlines
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Sat, Sep 20 - Fri, Sep 26
Spirit Airlines Logo
4:45 pm - 11:04 amCLE-SJU
18h 19m1 stop
Spirit Airlines Logo
1:59 am - 3:50 pmSJU-CLE
13h 51m2 stops
$233Spirit Airlines
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Mon, Aug 11 - Fri, Aug 15
Frontier Logo
11:37 am - 4:07 pmCLE-SJU
4h 30mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$242Frontier
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Sat, Nov 1 - Sat, Nov 8
Southwest Logo
2:45 pm - 11:45 pmCLE-SJU
9h 00m1 stop
Southwest Logo
4:05 pm - 9:55 pmSJU-CLE
6h 50m1 stop
$247Southwest
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Mon, Aug 11 - Fri, Aug 15
Frontier Logo
11:37 am - 4:07 pmCLE-SJU
4h 30mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$251Frontier
Find Deal
Tue, Aug 26 - Wed, Sep 10
Southwest Logo
11:40 am - 10:30 pmCLE-SJU
10h 50m1 stop
Southwest Logo
1:35 pm - 10:10 pmSJU-CLE
8h 35m2 stops
$284Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Cleveland to Caribbean flights

Get data-powered insights and trends into flights from Cleveland to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Cleveland to Caribbean flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Cleveland to Caribbean.

The cheapest ticket to Caribbean from Cleveland found in the last 72 hours was to San Juan, at $168 round-trip. The most popular route is from Cleveland (CLE) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $168.

Can I save money by flying with a layover from Cleveland to Caribbean?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $394, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Cleveland to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Cleveland to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Cleveland to Caribbean is May, when tickets cost $267 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $460 and $379 respectively.

What’s the cheapest day of the week to fly from Cleveland to Caribbean?

The average price of all round-trip flights from Cleveland to Caribbean clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Tuesday and more expensive on a Saturday. On your return trip to Cleveland, you should consider flying back on a Wednesday, and avoid Tuesdays for better deals.

How far in advance should I book a flight from Cleveland to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Cleveland to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Cleveland to Caribbean, you should book around 2 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonSeptember
Cheapest flight$88
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 23% increase in price.
Flight from Cleveland to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Cleveland to Caribbean?

    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 Cleveland to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Cleveland to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Cleveland to 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 Cleveland to Caribbean?

    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 from Cleveland to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Cleveland to Caribbean?

    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 from Cleveland to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $256 on average. Morning departures are around 13% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $348.

Reviews of the top 5 airlines serving from Cleveland to Caribbean

 
Need help choosing which airline to fly with from Cleveland to Caribbean? 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
DeltaOverall score based on 7980 reviews
7.9Comfort
8.2Boarding
8.5Crew
7.9Entertainment
7.3Food
Airline reviews

Delayed and took off even later than the scheduled delay time

8.0 ExcellentAnonymous, Jul 2025DTW - SEA
Read more Delta reviews

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

Boarding in Orlando was not good. Giant mob at the gate, should have been lines.

The worst. They don’t follow procedure for boarding per group. Flight got delayed for no understandably reasons, they changed our destination from PR to Miami, left us inside a plane for more than 8 hours, then cancelled flight in Miami leaving us stranded. Poorly managed re-accommodation for a new flight and overnight stay so I have to spend in a new ticket and my own hotel room to been able to get to my office next day. Lost 2 days of work and as a doctor, patients loosing their appointments. to other flights and besides

Decent clean onboard experience. Okay discount airline experience. Unfortunately, any customer service interactions are difficult and unhelpful. There is no service. Also, a premium seat only gets you premium boarding if you line up first. Once they start general boarding you must go to the back of the line. Not very premium

baggage clamed had to wait over a hour and half for all people on my flight it was terrible

The ticketing agents were rude but then we had a great gate agent very nice we had to ride a buss out to where the plane was parked but it was in some back corner of the airport when we got to the plane the captain who was great btw was cleaning the plane because the same rude ticketing agent told them they we not contracted to vacuum the plane. The ride to las Vegas was fine We had a connecting flight to Dallas. The flight was fine but when we arrived in Dallas everyone who flew on any frontier airlines the picked up bags from baggage claim D15 had to wait over a hour for their bags to start we arrived at 11:30pm ish to the gate we didn't leave the baggage clamed till 12:50 am very not happy and i used to fly frontier 4 times a week for work in Denver i will not be using them again

I was 2 hr arrive in the airport and 45 min in the line . After take to my turn . The agent tell me I’m later . I can not board . So my vacation was going to the floor . Just for their bad customer service agent in the airline

Frontier Airlines was AWFUL. I was an hour early for my flight and the lady refused to check me in. I had to purchase a whole new ticket with a different airline.

My flight was canceled I was promised a reginf still not received.

Late, terrible communication, horrible planning of passenger seating until the literal last minute. One of the worst flying experiences of my life. Y'all suck

Both legs of the flight were changed. The day of the flight and length of the trip.

Everything you need to know for your flight to Caribbean

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