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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 Cana2 stops$602
Santo Domingo
Santo Domingo2 stops$735
Montego Bay
Montego Bay1 stop$404
Nassau
Nassau1 stop$487
Kingston
Kingston2 stops$794
Providenciales
Providenciales1 stop$597
George Town
George Town1 stop$681
Aguadilla
Aguadilla2 stops$506
Punta Cana
Punta Cana2 stops$602
Santo Domingo
Santo Domingo2 stops$735
Montego Bay
Montego Bay1 stop$404
Nassau
Nassau1 stop$487
Kingston
Kingston2 stops$794
Providenciales
Providenciales1 stop$597
George Town
George Town1 stop$681
Aguadilla
Aguadilla2 stops$506
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 $399, 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 $603 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $881 and $831 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 15 weeks before departure.

Good to know

Low season

August
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 11% 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.
8.0
SouthwestOverall score based on 4202 reviews
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
Airline reviews

I like the staff members they were super nice and helpful very sweet people :)

8.0 ExcellentAleia, Sep 2026
Read more Southwest reviews

I like the staff members they were super nice and helpful very sweet people :)

Unfortunately, I left my headphone's case in the bag of the front seat. I was seating on 9C. Hopefully the found it and I can get it back. I have not been able to get in contact with Southwest. Other than that, everything went fine.

Maybe different snack selection. To much sodium in them. I know refrigerators are not available but there has to be healthier items.

Wifi was terrible. I couldn't get any work done on the long flight

It's a shame that SW was previously my preferred carrier until they started imposing all these fees (luggage, seats,etc) and pulling back on other perks. I only flew with them this time due to time frame I needed to be at destination. Wasn't provided gate info during check-in, Gate info wasn't displayed at airport until last minute, gate info didn't match what SW personnel announced at fate. Kind of a mess.

Flight was fine. Only thing was flight was delayed nearly 2 hours. Flight was originally scheduled to depart at 7:50pm but didn't depart until 9:50pm. I got home around midnight. It was later than desired and I had to get up early next day to take kids to practice. I have noticed that last flight of day on West Coast for Southwest always tend to have delays.

Wasn't expecting this, but, we actually ended up getting assigned to the first row of seats!!!!! The extra legroom came in handy

Trash experience on all my flights this week. Delay after delay. The flight I’m waiting for has been delayed 6 times and nearly 3 hours.

Southwest has been a nightmare. Delayed flights, missed connections, systems down. Never again am I flying southwest.

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Late flight, screens not working and still had to pay for a drink

great! appreciated the last minute upgrade to Comfort+ exit row, as well

Crew completed ignored our aisle when giving snacks and coffee

The seats were great and the service was even better. Thank you!

The WiFi on the plane was out. I also thought movie options were lacking.

They changed my seat assignment from window to middle. I have a physical need to sit by the window because of spinal issues. I unboarded in pain, I also was placed between 2 very large men. I am very disappointed and now dealing with the physical aftermath.

These Delta 717 jets are ancient. No entertainment and you have to pay for WiFi that barely works and goes in and out the whole flight. Delta should be ashamed flying this garbage.

The crew were awesome and ready to help as much as possible. The gate agent in Atlanta was tremendously helpful. The delays were ridiculous. Getting home at 4am when I could have driven home faster was unimpressive. Being delayed for countless hours through the night wasn't a great travel experience.

The staff and crew were wonderful. The delays were atrocious. The missed connections problematic. Getting home at 4am and having to go to work at 8 am, not a great situation. The gate agent in Huntsville was amazing. She helped everyone efficiently and with excellent problem solving skills. Her communication was helpful, timely, and thoughtful.

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.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

overall a very good travel experience - left on time, arrived early. Mostly a smooth flight. Polaris seats were excellent, very good service and nice food with options.

The very best airline service I have experienced. Better than domestic airlines first class and I flew Economy Plus!

When we boarded we were treated with care and it never stopped. Got towels before breakfast and after snacks was a lovely touch!

Price was crazy watch it if you Chan he your flight

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.

Legroom was decent, but the seat comfort was horrible; I believe the seat cushions have lost their cushion. I was uncomfortable and had back pain throughout the nearly five-hour flight. WiFi did not work despite my attempts to get it up and running. This was very frustrating as passengers all around me were streaming football games, movies, and accessing email and text messages. One flight attendant suggested it was my seat, but that makes no sense, given WiFi doesn't work that way. On another note, I rarely have a good experience with aainflight.com.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

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