$93 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 7/12. 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

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Best Caribbean Flight Deals from Cleveland

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$307
Montego Bay
Montego Bay1 stop$357
Oranjestad
Oranjestad1 stop$350
Nassau
Nassau1 stop$471
Kingston
Kingston1 stop$613
Simpson Bay
Simpson Bay1 stop$263
Providenciales
Providenciales2 stops$446
Port of Spain
Port of Spain1 stop$527
Bridgetown
Bridgetown1 stop$516
George Town
George Town1 stop$556
Willemstad
Willemstad1 stop$530
St. John's
St. John's1 stop$567
Puerto Plata
Puerto Plata1 stop$477
Aguadilla
Aguadilla1 stop$239
Punta Cana
Punta Cana1 stop$319
Santo Domingo
Santo Domingo1 stop$307
Montego Bay
Montego Bay1 stop$357
Oranjestad
Oranjestad1 stop$350
Nassau
Nassau1 stop$471
Kingston
Kingston1 stop$613
Simpson Bay
Simpson Bay1 stop$263
Providenciales
Providenciales2 stops$446
Port of Spain
Port of Spain1 stop$527
Bridgetown
Bridgetown1 stop$516
George Town
George Town1 stop$556
Willemstad
Willemstad1 stop$530
St. John's
St. John's1 stop$567
Puerto Plata
Puerto Plata1 stop$477
Aguadilla
Aguadilla1 stop$239

Cheap Flights from Cleveland to Caribbean

 
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

Sat, Jun 28 - Thu, Jul 3
 Logo
1:00 pm - 7:19 pmCLE-SJU
6h 19m1 stop
 Logo
5:01 am - 9:48 amSJU-CLE
4h 47mnonstop
Sat, Jun 28 - Thu, Jul 3
 Logo
1:00 pm - 7:19 pmCLE-SJU
6h 19m1 stop
 Logo
5:01 am - 9:48 amSJU-CLE
4h 47mnonstop
Tue, Jul 1 - Fri, Jul 11
Frontier Logo
8:25 pm - 12:44 amCLE-SJU
4h 19mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$178Frontier
Find Deal
Mon, Jul 14 - Thu, Aug 14
Frontier Logo
11:37 am - 4:07 pmCLE-SJU
4h 30mnonstop
Frontier Logo
6:00 am - 10:37 amSJU-CLE
4h 37mnonstop
$186Frontier
Find Deal
Fri, Oct 31 - Mon, Nov 3
Delta Logo
7:15 am - 4:25 pmCLE-SJU
9h 10m1 stop
Delta Logo
6:30 pm - 12:36 amSJU-CLE
7h 06m1 stop
$205Delta
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Thu, Aug 7 - Sun, Aug 10
United Airlines Logo
6:22 pm - 5:30 amCLE-SJU
11h 08m1 stop
United Airlines Logo
2:05 am - 11:14 amSJU-CLE
9h 09m1 stop
$275United Airlines
Find Deal
Wed, Sep 24 - Sat, Sep 27
United Airlines Logo
8:40 am - 11:57 pmCLE-SJU
15h 17m2 stops
United Airlines Logo
3:56 pm - 11:58 pmSJU-CLE
8h 02m1 stop
$295United Airlines
Find Deal
Wed, Jul 23 - Mon, Jul 28
Delta Logo
12:34 pm - 10:23 pmCLE-SJU
9h 49m1 stop
Delta Logo
7:00 am - 7:05 pmSJU-CLE
12h 05m1 stop
$305Delta
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Mon, Sep 22 - Fri, Sep 26
American Airlines Logo
6:00 am - 3:25 pmCLE-PUJ
9h 25m1 stop
American Airlines Logo
1:35 pm - 10:50 pmPUJ-CLE
9h 15m1 stop
$319American Airlines
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Mon, Sep 22 - Fri, Sep 26
American Airlines Logo
5:24 am - 3:25 pmCLE-PUJ
10h 01m2 stops
American Airlines Logo
1:35 pm - 11:08 pmPUJ-CLE
9h 33m2 stops
$323American Airlines
Find Deal
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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 $131 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 $131.

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 $367, 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 $266 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $462 and $381 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 Friday. On your return trip to Cleveland, you should consider flying back on a Wednesday, and avoid Saturdays 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. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.


Good to know

Low seasonSeptember
High seasonDecember
Cheapest flight$93
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 22% 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 $254 on average. Morning departures are around 15% 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.

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 7946 reviews
8.2Boarding
7.9Comfort
7.9Entertainment
7.3Food
8.5Crew
Airline reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

10.0 ExcellentHartaj, Jun 2025EWR - RDU
Read more Delta reviews

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Great flight! Only complaint I had was that I didn’t get breakfast that morning because I don’t eat eggs for breakfast.. I ate an energy bar I bought in the airport which I had never done before. Otherwise, another great Delta flight!

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

Terrible. Out flight was delayed for 21 (twenty one) hours. United is a joke.

Boarding was mayhem. Late boarding by 15 minutes because of lack of staff (missing 1 flight attendant. We had to wait for an arrival of another plane before we could board). Flight was a little rough, but cannot blame on airlines.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

Boarding was a breeze, however, two of the flights that I boarded with Spirit did not have Wi-Fi available.

Seats uncomfortable, hard to check luggage, etc. It was like the last flight out of Hanoi

Need screens for tv/movies. Seats are more cramped than any other airlines. Seats are hard. They don’t recline. And in flight time should not be used for sales pitches.

Good experience except for the drunk woman who was with a child. Sad

The ease of booking the flight was very good. Speaking with customer service was also good. However, the crew people are unfriendly and unwelcoming which I found this as unprofessional. As far as comfort it was mediocre. This was my first time flying Spirit and I chose them because of the flight times met my needs and my budget. However, I would be reluctant to fly on Spirit again. In addition, if the crew were more friendly and at least appeared somewhat happy and welcoming personally it would probably make the experience of flying with Spirit better.

Tell them to chose a better, less bumpy route :( my seat had no window all the way at the end 😔

Seats too hard, too much lumbar. Space between rows was extremely tight, so tight hard to place item under seat in front of me. No tv screens. Zero plugs for charging phones. Too many sales pitches

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It was horrible. We were not allowed on the flight by spirit staff at the gate during boarding because I had a guitar. The same guitar I had at check in which I paid for and they said I can take it on the plane. We missed our flight, lost our luggage, and had to pay another $900 to rebook flights. Worst travel experience ever and spirit staff are the worst staff ever.

Cancelled flight after I arrived at airport after 75 min drive and parking. Next flight was 4 days in the future. Had to scramble and buy a much more expensive flight on another carrier.

Book with frontier airlines with the mentality that they'll cancel your flight, kick you off and lose your luggage. Anything besides that is a win. Compare prices with other airlines (to include luggage) and if frontier is still worth it, book it but know all of their policies.

You get what you pay for nothing essentially but a hard uncomfortable seat that doesn’t recline and kids screaming all around you and chaotic boarding and limited check bag weight allowance when compared to other airlines

I never got to experience the flight because they delayed my first flight and I missed this one. Then Frontier didn't want to help me rebook a flight to get me to my final destination.

The Boarding process in Denver was chaotic, and since the line was so long, we were lined up very far from the gate. If there were any announcements from the gate staff, we didn't hear them. The flight attendants were spectacular. The only negative part of the flight was sitting by a 2 1/2 year old who was unruly and unfortunately had parents that matched his behaviors. Also, the restaurants in Denver on the E concourse, they didn't have food (passengers could only order 1 item on the entire menu) or the restaurants had 12-14 people waiting for orders to be prepared and another 6 people waiting to order. If you have a layover in Denver and need to grab food, be prepared to visit the shops with pre-packaged sandwiches, or you can visit another concourse but it may take a while to transit throughout the airport.

I liked the turn-style feature at gate 209B at LAX. Very efficient process. The gate staff also made several, clearly directed announcements so I felt very informed.

Although an hour and a half early was told by staff at check in they had overbooked and could not check us in for the flight.

The crew was delayed because they came on another flight that was delayed due to weather 10pm flight left at 1.30 am The airline made no effort to align alternate crew

I liked the price of the flight and the chance to buy a seat with no person seated in the middle seat.. Also the flight was right on time.

Plane was down graded and I lost my uncharged exit row with more leg room. No mention or offer of refund from podium. Flight attendant was nice to explain this happens often and that I could request a refund via online form submission. I did this and have heard nothing back.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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