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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$567
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay2 stops$417
Nassau
Nassau1 stop$512
Kingston
Kingston2 stops$787
Providenciales
Providenciales1 stop$598
George Town
George Town1 stop$682
Aguadilla
Aguadilla2 stops$676
Punta Cana
Punta Cana1 stop$567
Santo Domingo
Santo Domingo2 stops$625
Montego Bay
Montego Bay2 stops$417
Nassau
Nassau1 stop$512
Kingston
Kingston2 stops$787
Providenciales
Providenciales1 stop$598
George Town
George Town1 stop$682
Aguadilla
Aguadilla2 stops$676
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 $392, 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 $613 (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 $842 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 6 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.
7.9
SouthwestOverall score based on 4215 reviews
8.0Comfort
7.0Food
7.5Entertainment
8.1Boarding
8.6Crew
Airline reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

6.0 GoodRobert, Oct 2026
Read more Southwest reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

Stop asking fir people to check carry on and then bind are free. Then the wait to get your luggage is ridiculous. This particular flight came with a 45 min wait, after waiting in tarmac waiting for a gate inhaling jet exhaust. And how about those landings?! Do the pilots not know the earth is coming up under the descending plane?! This is the only airline I get sick on. Every. Time.

I understand the delays caused by the storm, but that doesn’t mean the systems had to be chaotic. The app showed one thing, the screens showed something else, and the gates kept changing every 10 minutes. It was a nightmare trying to figure out where to go.

Multiple delays due to weather in Chicago, but the crew did their best to get flights rescheduled and on to their destination. I felt like the crews handled a frustrating situation very well, kudos to them! I was very glad to not have a cancelled flight.

Southwest’s point to point system caused a 2 hour delay due to the crew being late from their inbound flight. Also, the WiFi and entertainment didn’t work on the plane.

One, we were met with more than six hours of delays with no information flowing from the airline to the passenger. I had to continually refresh for updates to departure time - which changed multiple times throughout the day. Updates were never pushed to me nor was an explanation provided for the delay until this morning. Two, while they claim that "due to the short flight" no beverage service would be provided. Our flight was mostly empty. I'd think given the massive inconvenience, SW could have shared a Diet Coke and some peanuts. And BTW, SW used to always make these available on this flight back in the day. Let's be honest, this is cost savings at the customer's expense.

Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.

It was the strangest thing. The flight attendant (who was not very friendly) took our drink orders and then never brought them. I’ve never had that happen before.

Delayed for no reason at all originally. Then they said it was due to weather conditions. Communication between kayak and Southwest was terrible because both displayed different delays and departure times for HOURS throughout the day. The plane then had technical issues which delayed us from taking off even longer. Didn’t actually take off until 11:45pm when the original departure time was 7:35pm. I didn’t get home until 1:30am the next day. I was exhausted and pissed off. I am not confident if I’ll fly southwest in the future or use kayak to book.

A) Checked my luggage at the gate but never got to pre board B) if we are helping with checking our carryon and waiting 40 minutes for it we should have some privileges c) luggage took 40-45 minutes to come.. d) I asked for another snack and was told the plane is full.. seriously a small snack

Gate agent and flight attendants were efficient, but more stern than warm.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

13 hour delay stuck in Detroit and missed a day of meetings. It was terrible

My flight was so delayed I would’ve missed my connection and had to cancel my trip

Seemingly unnecessary delays were compounded by a lack of communication from the flight crew which turned a four hour delay into an overly stressful experience.

I like Delta. I dislike the volume of announcements from the crew. They are not always easy to hear and typically repetitive.

I think the crew makes way too many announcements that are: 1) hard to hear in some cases and 2) repetitive. This detracts from entertainment and concentration if working or reading.

Everything was great. The only thing that wasn’t was the breakfast calzone which was basically warm bread. It was very tasteless and wasn’t good at all

Great crew. Comfortable seating. Nice overhead bin space. My app didn't allow me to check in for my flight to BOS. When I called Support, they didn't fix it, but just told me to check in at the airport. Seat back entertainment was great. Could be better if the audio could connect to Bluetooth.

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.

The flight was for my mom in wheelchair the staff in Newark wer not friendly took a long time to even get a wheelchair she almost missed her flight because they finally got a chair few minutes before boarding they had to rush her to the gate. They took her carryon and checked it as a bag told her don’t worry free of charge but they charge the credit card anyway. She also told me the seats are not comfortable at all as if they were broken she could feel the bars in the seat SFO staff was much better overall she had the worst experience

Wifi is very frustrating - could not connect and therefore unable to work on the trip

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

Premium economy was worth it. Great seats and good food.

Food was good. Clean aircraft. But why do the airlines make the seats so narrow?! Your executives should have ride in a seat so restrictive for 11 hours and see how miserable it is! When.we got to MUC they changed my boarding gate 3 times for my next 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.

I had to buy another ticket and you haven't reimburse me for it.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Had to find alternative flights because of AA lateness and bad planning

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