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Cheap Flights from Des Moines to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$577
Santo Domingo
Santo Domingo1 stop$702
Montego Bay
Montego Bay1 stop$458
Nassau
Nassau1 stop$558
Kingston
Kingston2 stops$2,043
Providenciales
Providenciales1 stop$638
George Town
George Town1 stop$678
Aguadilla
Aguadilla2 stops$781
Punta Cana
Punta Cana1 stop$577
Santo Domingo
Santo Domingo1 stop$702
Montego Bay
Montego Bay1 stop$458
Nassau
Nassau1 stop$558
Kingston
Kingston2 stops$2,043
Providenciales
Providenciales1 stop$638
George Town
George Town1 stop$678
Aguadilla
Aguadilla2 stops$781
Booking Insights

KAYAK's insights & trends for Des Moines to Caribbean Islands flights

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

Can I save money by flying with a layover from Des Moines to Caribbean Islands?

No, with an average price for the route of $404, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Des Moines to Caribbean Islands?

The cheapest month for flights from Des Moines to Caribbean Islands is February, when tickets cost $624 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $884 and $835 respectively.

How far in advance should I book a flight from Des Moines to Caribbean Islands?

To get a below average price on the flight from Des Moines to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 22% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

August
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 8% lower on average.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Des Moines to Caribbean Islands?

    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 Des Moines to Caribbean Islands.

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

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

    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 Des Moines to Caribbean Islands 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 Des Moines to Caribbean Islands?

    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 Des Moines to 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 4 airlines serving from Des Moines to Caribbean Islands

 
Need help choosing which airline to fly with from Des Moines to Caribbean Islands? 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.
7.9
SouthwestOverall score based on 4224 reviews
7.4Entertainment
7.0Food
8.1Boarding
8.0Comfort
8.6Crew
Airline reviews

the flight was significantly delayed. Not much was done by the airline to compensate passengers

2.0 MediocreChristopher Ryan, Oct 2026
Read more Southwest reviews

the flight was significantly delayed. Not much was done by the airline to compensate passengers

the flight itself was totally fine. The crew were great and very helpful. The flight was delayed, however, over an hour without a lot of information as to why.

Had to walk back and forth between concourses to figure out which gate I was supposed to be at. The app and the flight board in the airport had different gates listed. Was told numerous times to check bags only to get on the plane and find that there was plenty of room for bags. The flight was over an hour late which had me landing after the last train departed. WiFi was unusable

My experience was okay I changed my returning flight and I was charged extra money which I dont think should be the case, especially because I experienced small delays from my going flight. And many flights were either canceled or delayed after my original flight time. I believe some customers should have the ability to change flights due to certain situations

I've taken four flights with Southwest within the last three months and every single flight was delayed.

It was great and arrived home a little sooner than expected which is nice.

I fly out every other weekend and this is the 4th time my flight has been delayed at Southwest. I will be flying out twice a month on average for the next 6-7 months. If this is your average ‘on time’ I’ll probably be flying another airline.

WiFi was inoperable - second in four recent Southwest flights where that was true. I need WiFi for work and if Southwest cannot provide, I’ll stop using it

It’s too cold like fridge and they don’t offer a blanket with expensive price

Boarding now takes twice as long since going with assigned seats.

Bad. Flight was delayed due to maintenance issue with Delta. Seats were small, no service, bag got broken on initial flight. Cramped and hot. Sitting inside with no ac.

Flight attendent didn't let me sit in the empty window seat literally next to me. Doors had closed already so I moved over. She came over, asked for my ticket and made me switch back to the middle. The man on the aisle and I were right on top of each other. Seemed like a real power trip for no reason at all.

The flight was delayed and passengers were told that they will miss connections as flight may get 40-55 min late.

The flight from Atlanta to Tallahassee was delayed, not such a big deal because it arrived almost the same original time. Most of my complaint is that one of the boarding agents and one of the flight attendants seemed bothered and were not very friendly.

Be on time. No issues with weather etc. entirely on airline.

Good flight — left on time due to on time arrival of Pittsburgh flight

I think in the future I cannot fly anything less than Comfort plus. The seats vary depending on the plane. The people are extremely nice and funny. I try to only fly Delta if I can help it.

delayed take-off, then had to circle in air for awhile, wi-fi did not work, then the cabin got extremely hot multiple times and the luggage was at wrong carousel at LGA. In addition, plenty of overhead space so they checked bags too early. Horrible flight.

Flight was fine, it was on-time and was not cancelled which is very good. However the small cabin bag was forced check-in although once I entered into the flight there was lot of space which would have accomodated 10 such bags. Moreover this caused delay on arrival of my bag due to which I missed my booked cab and had to wait for another 20 minutes before the next taxi (Uber) arrived.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

Seats are uncomfortable and left me in pain in my tailbone area. I got about one hour of sleep.

Phx - ORD was nice 737 with starlink and the ORD - grr was ancient bare bones airbus with not even a power port lol

No white linens in premium economy . Salad was literally frozen. Food was terrible. No snacks. Ran out of food. I asked a flight attendant for snack on hour 8!of 16 hour flight and she said they don’t offer snacks and called me crazy for not having my own snacks for the flight.

It was easy to board, and the staff was friendly and helpful. What could have been better is that I shouldn't have to pay extra for a seat that doesn't recline.

Was on the plane sitting longer than the actual flight in air was, boarded at 5:45p and didn't take off until 6:50p flight was only about 30 minutes long. Just was poor experience will booking more with American Airlines.

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

It was better than excellent. The staff in Mason City were great. The young woman that pushed my wheelchair did more than could be expected of her. She came from India 17 years ago. I don't remember her name.

Very rough getting into denver. my kid threw up it was so rough.

Liked that we left on time for each flight. Snacks not the best, but we're okay.

I had requested wheelchair assistance prior to flight. The airport staff had no record of it. It was not provided at Cedar Rapids which was a small airport, so I managed on my own. At O'Hare airport the same thing happened. The staff told me they had no record of my request for a wheel chair. But they finally provided it after a delay when I insisted that I needed it.

The amount of gate changes and delays is completely unacceptable. This has happened on 3 of 4 trips between Chicago and Dallas in 2026.

I didn't like anything about this flight. The only reason anyone drinks Jack is because you ran out of Woodford. You should know to stock more Woodford. When you wait of first class hand and foot from the minute they get on the plane 5 feet from me but then start service from the rear of the plane so main cabin plus gets the scraps, that's how you get people to stop flying your airline.

American Airlines was horrible! The layover flight to DFW was delayed with no clear communication and for us having to stay the whole day which led to staying a night in Dallas was comped with 2 $12 dollar vouchers and a crappy hotel. We missed a whole day in Tokyo for our honeymoon and stressed the whole 24 hours. We were supposed to leave at the same time the following day, but that was delayed hours again. And instead of letting the delayed flight go first, they let the flight that was scheduled ahead of us. American should refund us the day wasted in Dallas that should have been in Tokyo! We had lost out on paid events that we can’t get refunded. When we finally did leave, it was a good flight. You would think that was the only issue with American but we from the LAX layover, we were delayed 6 hours and were given a $12 dollar voucher that covered a drink only. The only communication we were given then was that because they were delayed in a prior flight we were delayed again. I don’t understand why it was only with American that we had such a bad time with! They have definitely left a sour taste in our mouths for our honeymoon! And then they did send an email saying we could have 2K miles…. For what? To be delayed into another day and miss our flight again?

The plane was experiencing problems with the HVAC system, it was very cold in the front of the plane and very hot in the back.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

In flight connectivity (via T-Mobile) was often not working.

Terrible. Internet/kiosk glitch prevented baggage checkin. Line at ticket co in Ter was under serviced and did not move. Agents did not call for flight but rather allowed time to pass. Then told each person as they reached the front if line that it was too late to check bags so they’d have to rebook flights. At least 15 people missed the flight as a result of this incompetence.

It was exactly what I expected, actually arriving sooner than scheduled.

Terrible, they canceled my flight due to an issue they had, couldn't fly me into the same place within 24 hrs so had to fly in 2.5 hrs away from my destination and spend even more money. The customer service was terrible (except at the airport in Charleston). Had to call to get my checked baggage fees reimbursed 2 wks later in which one customer service agent was very rude, wouldn't listen and then hung up on me. The second lady I spoke with was actually able to help me with that part thankfully. Would not recommend flying AA.

Delayed, missed connecting flight, ground crew double charged for international charges, were super rude and told me to just”deal with it” when I complained. Horrible airline, very frustrating.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental