$68 Find Cheap Flights from Cincinnati 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 Cincinnati to Caribbean departing on 1/18. 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
0 bags

Search hundreds of travel sites at once for deals on flights to Caribbean

In the last 7 days travelers have searched 41,299,237 times on KAYAK, and here is why:

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Best Caribbean Flight Deals from Cincinnati

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$240
Santo Domingo
Santo Domingo1 stop$344
Montego Bay
Montego Bay1 stop$348
Oranjestad
Oranjestad1 stop$391
Nassau
Nassau1 stop$392
Simpson Bay
Simpson Bay1 stop$433
Kingston
Kingston1 stop$640
Providenciales
Providenciales1 stop$492
Bridgetown
Bridgetown1 stop$605
George Town
George Town1 stop$506
Willemstad
Willemstad2 stops$555
Puerto Plata
Puerto Plata2 stops$650
St. John's
St. John's2 stops$590
Aguadilla
Aguadilla1 stop$158

Good to know

Low season

September

High season

March

Cheapest flight

$68
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Cincinnati to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Cincinnati 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 Cincinnati to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Cincinnati 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 Cincinnati 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 Cincinnati 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 Cincinnati 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 Cincinnati to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Book at least 1 week before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly from Cincinnati is September.
  • Morning departure is around 20% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

Top 5 airlines serving from Cincinnati to Caribbean

Need help choosing which airline to fly with from Cincinnati 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.
8.1
SouthwestOverall score based on 4821 reviews
7.7Entertainment
8.2Boarding
8.7Crew
8.1Comfort
7.2Food
Airline reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

10.0 ExcellentWilliam Drew, Dec 2024SJC - HNL
Read more Southwest reviews

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Much better than the.last. flight on SW on Thanksgiving day

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

The movies using Southwest WiFi kept pausing and I had to restart multiple times.

It went well. Plane wasn't full. Will be great when assigned seating is in place

Everything was great except the food. The pretzels are really crappy.

For the first time in a long time we had a flawless experience with Southwest. Both flights were early and no mechanical errors at all. We were shocked and pleasantly surprised 😮.

It was fine. For some reason the flight was much longer than usual. It may have been explained, but I had noise cancelling earbuds on and missed a couple of announcements. The crew was fine, but there was a flight attendant who kept telling dumb jokes, occasionally one I found distasteful. This was my second time with him, but luckily it was a late flight so he didn't do as many. But I heard all of today's jokes twice, which was two times too many. Good takeout and landing.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

I was with one of the last zones to board. It was kind of annoying to finally get called to board and my whole section was already on the plane. Clearly they boarded with previous zones. So by the time I got on board, there were no spaces for my luggage above my head. I had to put my luggage 4+ rows behind me, which meant that I had to wait even longer to get off the plane, since I had to wait for those rows to clear the aisle before I could retrieve my luggage and exit the plane. This also held up the plane cleaners, as they couldn't service my row until I cleared it, so they were all standing there waiting for me, while I'm standing there waiting for the other passengers to clear the aisle. Anyways, I wasn't in a rush this time, so I just waited, but I could see that being a problem in the future. Now, I could have checked my luggage, of course, but coincidentally, a friend of mine on the same flight got their luggage damaged (wheel completely knocked off) and was told by the Baggage Attendant in the airport that Delta doesn't "cover wheel damage" on luggage. This was disappointing to hear. I'm glad I didn't check mine through. If it were my luggage, I'd be highly frustrated to hear that. It makes me not want to check my luggage in the future.

The dear was very limited in space. I could put my water bottle in seat basket. Also, there was no inflight entertainment in the delta app?

Typically I give delta excellent reviews. Our flight was delayed 2hrs, I was one of the fortunate ones who were able to get to my connecting flight. Also, annoying that on the connecting flight boarding personnel make me put away a small bag into my carryon. It small enough to put in back pocket seat, why hold me and the line up to just push it into my carryon.

Logan airport construction meant that boarding was chaotic crowded and delayed

Everything was great. Great service, excellent communication, and early arrival

We were forced to wait nearly 50 additional minutes before leaving the terminal.

Free Wi-Fi is good. That’s all - food mediocre, unfriendly crew, poor communication after trying to file a claim for my lost bag, which Delta didn’t even know was lost until I told them.

Delta flight attendants poorly managed the boarding process and overhead storage. My bag was checked last minute and no claim ticket was provided. My bag is now lost. Complete incompetence by all flight crew involved.

Inexpensive, got an exit row aisle aeat with no middle passenger, bought a great breakfast sandwich, flight comfortable & arrived ahead of schedule.

Customer service at the gate in the flight was exceptional. On time. Aircraft and seat was decent. Thanks Delta. 💗

We arrived early and finally made it to our gate almost an hour after.

The reason I don’t fly United. No in seat entertainment for a long flight and inconsistent WiFi and entertainment available from my device.

We were delayed 3x and because I didn’t purchase my tickets directly from United Airlines I was told I Have to take care of it myself so I called Underpricer and they helped me but before I changed my flights I took the risk of sticking by what my tickets were and was lucky to have gotten on the original all flight with only 15 mins before take off. not sure if I will do this again

horrible website for checking in- no option just to write the passport number; ludicrous

The planes are so dirty! Food crumbs and finger print smudges, Dust over the vents and carpet stains. It’s disgusting.

Everything good until we waited for jet bridge at SFO. Then pilot gets on speaker & said it won’t reach plane- too short, need to go to different gate. Then 5 min later, adjusted plane/jetbridge & all ok?!?

Nothing, whole flight was a nightmare, was forced to check my carryon bag at the gate, staff was rude and unprofessional

David went above and beyond to make our flight the best that it could be

Was a pain having to leave the plane and reboard but glad the plane was fixed

How badly can you screw up baggage claim? We were told to go to baggage claim too for our bags from this flight. Another flights bags were there. They finished up. More bags from a different flight arrived. Our bags did not Finally the baggage claim belt stopped working and and are flight was still listed on the arrivals for that baggage claim 2. And then nothing It turns out that they had been delivered not only the United baggage claim but far away on a Delta baggage claim No I never told us. It was only the people looking around who had been on the flight But I’m sure there was plenty of time for the employees to raffle through the bags and steal whatever they wanted

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

Flight areas delayed 3 hours , train in the airport didn’t work

Flight attendant walked away once they landed and we were forced to wait another hour after an already 3hr delay.

No overhead space so all carryons were checked. No internet.

The flight was on time and everything went very smoothly.

A thousand choices for movies and nothing to watch. I avoid 'R' rated shows and others with violence and sexual content, which results in a handful of flicks to view and I have them already.

I think I paid for an extra legroom seat and to be honest, there was not a lot of space available for my not very long legs. The flight was totally full and the staff did everything possible to meet the needs of all passengers. My only concern was for the size and spacing of my seat.

Typically, I am always impressed with American personnel. These you run into the rude old hags that are still around. I can tell over my 40 years of flying with them, they have made strides in improving their attitudes.

Two issues. The plane was old and dirty. The armrest looked like an old car that had the vinyl rubbed off. The Seats in these aircraft are about as hard and uncomfortable. I want to tour Italy for a month and I want to buy a one-way ticket to Thailand but I will not sit in the seats these planes have. It is seriously stupid how hard they are.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride. At boarding, the staff could have more pleasant even though it may be an intense time.

Delayed each time on a round trip with no significant weather interference. Updates to flight times came after the fact. 30 min behind in boarding and board and phone still show an on time departure. Some mysterious extra 300 miles that came so surprising they had to fuel while we were already on board?

A lady asked to stop the flight after the tunnel pulled away and we began to depart a flight that was already hours late. The attendance respectfully stopped the the plane and had the tunnel return. After the tunnel returned the passenger claimed to have changed her mind . The tunnel was then put in reverse and the passenger remained on the plane .. They should have sent the sick passenger off the plane like initially replaced. They existed a couple off the plane prior to that situation.. So.. all and all.. it was a long and flight.. .

terrible cascading delays and unhelpful customer service. uncomfortable plane. crew was great, however!

I ended up paying $70+ dollars to for a carryon because the website is confusing and misleading. I now realize I did not need to pay that. I request a refund. I will pay extra to other airlines and not fly Frontier again.

With frontier you get what you pay for. The flight was two hours late. It’s a tight fit for the number of people they bring but you get to where you’re going cheap. Sometimes that’s more important than a nifty drink and cool TV..

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

Although we received an email from Kayak AND the airline, turns out we were not on Frontier’s manifest for the flight. We had to purchase tickets at the gate. Not sure where this transaction fell apart, but it did. We are now disputing the charges for the SLC to PDX flight originally booked through Kayak.

We had an awful experience getting our bags checked in. Frontier’s check in on the app manipulated us into buying the business package because that was the only option available for a checked bag which included two checked bags per person which we did not need. Upon arriving to the airport, we stood in line for what seemed like forever at the baggage check in and there was no one available at the counter. We were first in line and we were afraid we were going to miss our flight due to the baggage attendant being late. After realizing there were a lot of other people waiting at the baggage check in and no one available. I reached out to Frontier and could not get any customer service so I had to call the airport to page the baggage attendant to send someone to the counter to check in our bags before we were able to go through security , I finally spoke to the attendant at the counter and explained to her that we had to pay for two checked bags person a total of six bags when we only had a total of three bags between three people she said to reach out to Frontier and they would issue a refund for the three bags that we paid for and did not need. I reached out to Frontier which I was not able to reach anybody by phone so I had to go through their automated chat feature, which sent me around in circles until I finally reached a representative to assist me. I explained to them what happened and they explained that they were not able to assist me. I continued to push the issue with them as this was very frustrating and they finally put in a customer service ticket where we were issued a flight credit and we were so disappointed because after this experience, we NEVER want to fly Frontier again, and we do not want a credit that we will not use. Frontier charged us almost $500 for us to check three bags which is absolutely absurd! The customer service agents were not able to offer anything else other than a flight credit and I do not feel like my frustrations were truly heard , we will never use Frontier Airlines again ! Truly Theft by Manipulation! They should be ashamed!

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

One crew member was rude about our bags. Be nice about it. We don’t fly a lot. And the fact that you have to pay for a carry on is ridiculous

Book cheap flights from Cincinnati to Caribbean

Recent round-trip flight deals

1/20Mon
1 stopFrontier
6h 41mCVG-SJU
1/27Mon
1 stopFrontier
13h 41mSJU-CVG
$128
1/22Wed
1 stopFrontier
21h 17mCVG-SJU
1/27Mon
1 stopFrontier
13h 41mSJU-CVG
$129
4/27Sun
1 stopAmerican Airlines
16h 14mCVG-SJU
5/1Thu
1 stopAmerican Airlines
5h 48mSJU-CVG
$194
1/31Fri
1 stopAmerican Airlines
11h 49mCVG-SJU
2/8Sat
2 stopsAmerican Airlines
11h 05mSJU-CVG
$219
1/22Wed
1 stopDelta
7h 32mCVG-SJU
1/28Tue
1 stopDelta
10h 30mSJU-CVG
$224
1/5Sun
1 stopDelta
8h 50mCVG-SJU
1/18Sat
1 stopDelta
10h 09mSJU-CVG
$229
1/5Sun
1 stopUnited Airlines
7h 38mCVG-SJU
1/14Tue
1 stopUnited Airlines
9h 46mSJU-CVG
$239
1/28Tue
1 stopUnited Airlines
7h 42mCVG-SJU
2/5Wed
1 stopUnited Airlines
9h 46mSJU-CVG
$284
2/27Thu
2 stopsSouthwest
10h 50mCVG-SJU
3/3Mon
1 stopSouthwest
8h 05mSJU-CVG
$437
5/2Fri
2 stopsSouthwest
10h 55mCVG-SJU
5/5Mon
1 stopSouthwest
7h 10mSJU-CVG
$453

Search by stops

Search by airline

Search by price

Recent one-way flight deals

1/18Sat
1 stopFrontier
15h 59mCVG-SJU
$68
1/10Fri
1 stopFrontier
7h 51mCVG-SJU
$81
1/26Sun
2 stopsUnited Airlines
14h 22mCVG-SJU
$97
5/13Tue
1 stopDelta
8h 29mCVG-SJU
$117
1/30Thu
1 stopAmerican Airlines
16h 51mCVG-SJU
$132
5/4Sun
1 stopAmerican Airlines
16h 09mCVG-SJU
$135
5/10Sat
1 stopDelta
6h 32mCVG-SJU
$152
3/13Thu
1 stopUnited Airlines
7h 38mCVG-SJU
$157
1/10Fri
2 stopsSouthwest
9h 45mCVG-SJU
$227
1/18Sat
2 stopsSouthwest
10h 05mCVG-SJU
$256

Search by stops

Search by airline

Search by price

Last minute flights from Cincinnati to Caribbean

Last minute flight, train and bus deals

12/23Mon
multi-stopFrontier
12h 40mCVG-SJU
12/25Wed
multi-stopFrontier
13h 26mSJU-CVG
$438
12/23Mon
multi-stopFrontier
27h 24mCVG-SJU
12/30Mon
multi-stopFrontier
17h 46mSJU-CVG
$439
12/23Mon
multi-stopAmerican Airlines
10h 15mCVG-SJU
12/28Sat
multi-stopAmerican Airlines
15h 20mSJU-CVG
$444
12/23Mon
multi-stopFrontier
12h 40mCVG-SJU
12/25Wed
multi-stopFrontier
13h 26mSJU-CVG
$468
12/24Tue
multi-stopAmerican Airlines
18h 58mCVG-PUJ
1/10Fri
multi-stopAmerican Airlines
18h 04mPUJ-CVG
$484
12/21Sat
multi-stopDelta
9h 39mCVG-MBJ
12/28Sat
multi-stopDelta
6h 50mMBJ-CVG
$618
12/21Sat
multi-stopDelta
9h 39mCVG-MBJ
12/26Thu
multi-stopDelta
8h 30mMBJ-CVG
$683
12/23Mon
multi-stopSouthwest
12h 10mCVG-SJU
12/30Mon
multi-stopSouthwest
16h 25mSJU-CVG
$894
12/23Mon
multi-stopUnited Airlines
12h 09mCVG-SJU
12/24Tue
multi-stopUnited Airlines
8h 03mSJU-CVG
$924
12/23Mon
multi-stopUnited Airlines
21h 22mCVG-SJU
12/27Fri
multi-stopUnited Airlines
8h 03mSJU-CVG
$969

Search by stops

Search by airline

Search by price

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.