$65 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 2/24. 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

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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$288
Santo Domingo
Santo Domingo2 stops$311
Montego Bay
Montego Bay1 stop$314
Oranjestad
Oranjestad1 stop$364
Nassau
Nassau1 stop$369
Simpson Bay
Simpson Bay2 stops$414
Kingston
Kingston1 stop$359
Providenciales
Providenciales1 stop$503
Bridgetown
Bridgetown1 stop$581
George Town
George Town1 stop$486
Willemstad
Willemstad1 stop$511
St. John's
St. John's2 stops$416
Puerto Plata
Puerto Plata2 stops$529
Aguadilla
Aguadilla1 stop$160

Good to know

Low season

September

High season

March

Cheapest flight

$65
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 17% 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 22% 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 4659 reviews
8.2Boarding
7.2Food
8.1Comfort
8.7Crew
7.7Entertainment
Airline reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

10.0 ExcellentRachel, Jan 2025TPA - MDW
Read more Southwest reviews

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Wi Fi was horrible kept cutting out the whole time and too expensive

I really like open seating. I hate that I've heard this is going away. This is one of the unique things that makes Southwest my goto choice.

Boarding was a little late, but made up for it. It was quick to taxi to the runway, since it's a smallish airport.

Excellent! Only question is how we check in at exactly 24 hours in advance and end up at the end of the B boarding group

Multiple delays and gate changes. Arrived at final destination 6 hours late. All rental cars had been taken.

Employees were kind and funny, as always! Flight was late but no announcements were made for people with tight connections to help them transition quickly. No service due to turbulence.

It was 2 hours 45 minutes late, for no apparently clear reason.

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

Great service. Great staff. Boarding was a little slow, but I think there was a service dog slowing things down.

Flight left early and arrived early. the whole trip was excellent.

Seats were really tight and the seat belts did not give enough slack.

I like in St George and prefer to fly out of CDC than SGU. Hopefully, they will continue the flights out of Cedar

Broken jer bridge. Poor communication about it. Lost 2 of 4 luggage pieces

Overall, it was okay. Seat was a little cramped. Would’ve liked more substantial snacks or opportunity to buy some.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Other then mechanical/ computer problem and 3.5 hours flight delay the flight was great. I guess that what happened when you fly an old airplane now a day.

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?

I liked all the informational texts. I always knew where to go and when .

Boarding is very confusing. They have Line 1 and Line 2 and many many Boarding groups. Everyone lines up under those two lines long before they call zones. If you have a higher zone 2 like I did due to a Premium Plus ticket, it’s very awkward having to ask each person which zone they have. Extremely chaotic process. On board the flight attendants had no charisma whatsoever, even to us paying extra for an upgraded cabin. I asked for a chamomile tea after dinner (as no coffee or tea was even offered) and the FÃ said they didn’t have even though listed on the drink menu. Also, the mid flight service was entirely skipped which was a soup and sandwich combo. Supposedly had a variety of snacks mid flight too but those never materialized either. A few times I walked Back there, not a single flight attendant acknowledged me as they were all deep into their iPhones. I simply Wanted a glass of water since ZERO water runs were made on this 9hr 30 min flight.

Liked the hospitality . The ight took us 6 hrs to get from fort myers to ewr.

Oh my gosh, I loved my experience with United! they made me want to travel more often.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

Smooth flight. As always dinner could have been more generous. Breakfast was great.

AWFUL. I have had the experience of traveling with many airlines across the world, and hands down United Airlines is the worst. Not one flight was on time, and I don’t think I met one crew member or staff member who wasn’t rude.

The service and food needs to improve to catch up with other international flights

Small plane, so no entertainment. Hour delay! Nobody explained wht the delay was all about.

I wasn’t happy with the hour delay from Dallas to McAllen, but that is the nature of travel. I don’t like to fly in general because of all of the problems all the time.

It went up and down at the right time and place. I’m happy with that outcome.

Staff at the gate were incredibly rude, hostile and threatening. Never fly American Airlines.

DO NOT BOOK THROUGH AMERICAN AIRLINES IF YOU HAVE ANY ADDITIONAL NEEDS. Great flight, crew etc. it wasn’t full so had space to stretch out Only downside was there was no GF option for my partner. We booked through American and it was a Qantas flight so despite contacting both airlines to confirm, she didn’t have a gluten free meal for the 16 hour flight (nor the flight in the other direction). The flight attendants did their best to accommodate but it was not super substantial.

Would have been good to have a meal since it was a 5.5 hour flight

Same problems with delays in Dallas. This was weather related and due to the incoming flight being delayed. This was the flight that was delayed due to a missing flashlight which turned out not to be missing.

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

I had a horrible experience from the time I dropped off my bags until the time I landed. The staff taking the bags at the check-in counter prior to security, forced me to check my baby stroller, even though it weighed less than 20 pounds. their excuse was that the wheels were too big. I have never had an issue gate checking this exact same stroller in the past either on American or on any other airline. when I asked for the agent to show me the rule about the size of the wheels on strollers, they told me to look it up on the AA website. I did so, and did not find any indication that wheel size was a problem for gate checking strollers. The only limitation would be the weight of the stroller which mine was below. I was left with a one-year-old child and all of my carry-on luggage, diaper bag, and the like to walk around the airport without the assistance of a stroller and had the same issue when I exited the plane and had to go all the way to baggage claim without a stroller. In addition, while on the airplane, I was told I can only get one bag of cookies as a snack, even though I was with a child. Apparently my child and I were supposed to share a cookie. While this latter issue is a minor one, it is just another example of the absolutely horrible customer service that American Airlines provides. In addition, the 737 aircraft that I was on was extremely hot and the air vents above the seat were so far away from the aisle and middle seats that it was comical. I could barely reach the air vent to adjust it. I had to ask the person in the window seat to do it for me. The whole experience was just a nightmare.

My experience with the phoenix airport was terrible, the personnel lay the ticket counter charged me for a carry on that fit in the carry on size box, and the two women I spoke with were terribly rude and not willing to help.,,, there was one lady “candy” on the flight crew that was amazing and is the only reason I stayed on the flight at all, because the other stewards helping people to get seated on the plane were terrible

I loked walking out on the tarmac to board and no first class. I didn't like that they have no snacks or onboard wifi to bide your time.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

The seats were extremely hard and uncomfortable, even for a budget airline.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Charging $74 for one checked bag is outrageous. I will never fly Frontier again.

Boarding was very well executed. Got my bag right away.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

Our flight was suppose to leave at 9pm and we didn’t board until after 3am. We lost a whole day at our hotel and half a day at a park we paid a lot of money for.

It was a redeye flight, so every passenger just wanted to sleep, but through the entire flight, the flight crew made announcements over the loudspeaker at maximum volume every few minutes making sleep impossible. For example: it’s 2am, and the crew decides to give an extremely detailed announcement about snacks and beverages for sale. And 3am is the perfect time to wake up everyone with a lengthy announcement about how to get a coffee refill and how to take advantage of new offer from frontier for a credit card.

Book cheap flights from Cincinnati to Caribbean

Recent round-trip flight deals

2/3Mon
1 stopFrontier
7h 14mCVG-SJU
2/6Thu
1 stopFrontier
8h 02mSJU-CVG
$129
3/1Sat
1 stopFrontier
12h 14mCVG-SJU
3/4Tue
1 stopFrontier
12h 23mSJU-CVG
$130
1/29Wed
1 stopFrontier
6h 59mCVG-SJU
2/3Mon
1 stopFrontier
16h 35mSJU-CVG
$135
2/3Mon
1 stopUnited Airlines
6h 32mCVG-SJU
2/5Wed
2 stopsUnited Airlines
14h 08mSJU-CVG
$205
2/3Mon
1 stopUnited Airlines
6h 32mCVG-SJU
2/6Thu
2 stopsUnited Airlines
13h 27mSJU-CVG
$212
2/3Mon
1 stopAmerican Airlines
15h 13mCVG-SJU
2/6Thu
2 stopsAmerican Airlines
10h 08mSJU-CVG
$235
2/2Sun
2 stopsAmerican Airlines
9h 28mCVG-SJU
2/4Tue
2 stopsAmerican Airlines
10h 28mSJU-CVG
$265
2/26Wed
1 stopDelta
7h 29mCVG-SJU
3/3Mon
1 stopDelta
10h 28mSJU-CVG
$325
3/25Tue
1 stopDelta
9h 08mCVG-SJU
4/4Fri
1 stopDelta
7h 48mSJU-CVG
$360
3/25Tue
1 stopSouthwest
9h 10mCVG-MBJ
3/28Fri
1 stopSouthwest
7h 40mMBJ-CVG
$633

Search by stops

Search by airline

Search by price

Recent one-way flight deals

2/24Mon
1 stopFrontier
6h 27mCVG-SJU
$65
2/22Sat
1 stopFrontier
15h 36mCVG-SJU
$68
1/26Sun
1 stopDelta
7h 02mCVG-SJU
$118
1/26Sun
2 stopsAmerican Airlines
9h 28mCVG-SJU
$120
1/26Sun
2 stopsAmerican Airlines
9h 28mCVG-SJU
$121
3/2Sun
2 stopsUnited Airlines
10h 55mCVG-SJU
$147
3/19Wed
2 stopsUnited Airlines
13h 43mCVG-SJU
$151
4/2Wed
1 stopDelta
9h 45mCVG-PUJ
$232
1/21Tue
2 stopsSouthwest
9h 45mCVG-SJU
$262
3/22Sat
1 stopSouthwest
8h 10mCVG-SJU
$323

Search by stops

Search by airline

Search by price

Last minute flights from Cincinnati to Caribbean

Last minute flight, train and bus deals

1/20Mon
multi-stopFrontier
11h 24mCVG-SJU
1/27Mon
multi-stopFrontier
11h 48mSJU-CVG
$320
1/19Sun
multi-stopFrontier
7h 49mCVG-SJU
1/23Thu
multi-stopFrontier
8h 02mSJU-CVG
$326
1/19Sun
multi-stopAmerican Airlines
9h 05mCVG-SJU
1/23Thu
multi-stopAmerican Airlines
11h 06mSJU-CVG
$460
1/17Fri
multi-stopAmerican Airlines
16h 51mCVG-SJU
1/25Sat
multi-stopAmerican Airlines
11h 20mSJU-CVG
$477
1/19Sun
multi-stopUnited Airlines
13h 28mCVG-SJU
1/22Wed
multi-stopUnited Airlines
12h 19mSJU-CVG
$525
1/20Mon
multi-stopUnited Airlines
13h 28mCVG-SJU
1/26Sun
multi-stopUnited Airlines
9h 46mSJU-CVG
$546
1/20Mon
multi-stopSouthwest
10h 35mCVG-SJU
1/27Mon
multi-stopSouthwest
11h 25mSJU-CVG
$621
1/19Sun
multi-stopAir Canada
18h 50mCVG-NAS
1/21Tue
multi-stopAir Canada
25h 51mNAS-CVG
$639
1/17Fri
multi-stopAir Canada
20h 40mCVG-PUJ
1/20Mon
multi-stopAir Canada
25h 06mPUJ-CVG
$686
1/19Sun
multi-stopSouthwest
12h 15mCVG-SJU
1/21Tue
multi-stopSouthwest
9h 15mSJU-CVG
$755

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.