$215 Find Cheap Flights from Des Moines to Caribbean Islands - Compare and Save

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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$551
Santo Domingo
Santo Domingo2 stops$605
Montego Bay
Montego Bay2 stops$404
Nassau
Nassau1 stop$544
Kingston
Kingston3 stops$767
Providenciales
Providenciales2 stops$678
George Town
George Town2 stops$544
Aguadilla
Aguadilla2 stops$556
Punta Cana
Punta Cana2 stops$551
Santo Domingo
Santo Domingo2 stops$605
Montego Bay
Montego Bay2 stops$404
Nassau
Nassau1 stop$544
Kingston
Kingston3 stops$767
Providenciales
Providenciales2 stops$678
George Town
George Town2 stops$544
Aguadilla
Aguadilla2 stops$556
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 $389, 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 $589 (return) on average. On the other hand, the most expensive months are March and November, when the average cost of round-trip tickets is $769 and $753 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 26% 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

Cheapest flight

$215
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Des Moines to San Juan

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 4195 reviews
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

Terrible - the flight was delayed taking off after boarding. Then the flight circled lga before landing. Significant delay

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

Everything went smooth from check in, thru TSA, then boarding, and a smooth flight to ATL.

There were weather issues in the area apparently; however, that was not obvious from what we saw outside of LaGuardia. We were delayed leaving (which I understand); however, once we were on the plane we didn't leave for a long time. It may have been two hours?? - all I know is that we sat there for a long time with no information as to why we were not taking off. Finally, after 45 minutes to an hour (maybe?), the pilot gave us an update that no planes were able to go in the our flight path direction (or something like that) due to weather. There was nothing additional added. What does this mean? Why is this? What are the options? When will you give us another update? There were no updates for maybe another 30-45 minutes. There was no explanation as to why we couldn't be rerouted to avoid the weather. We had no information at all. We just sat on the plane (for about 2 hours) with very limited information. All I would have wanted is an explanation as to what was going on. Tell me there is bad weather coming our way. Tell me they are working to reroute us around it (which is what they did). Tell me SOMETHING.

My 4pm flight did not leave until about 10pm. I did not enjoy this experience.

I had an extensive delay on my previous flight and we had another delay due to the crew not being there. We were scheduled to have a late arrival but due to the delay it was even longer.

Had one of the worst travel experiences I've ever had. 1.5-hour delay turned into being held on the tarmac and our pilots timing out. Was supposed to take off at 4pm and didn't take off until 10:30pm.

Delayed 7 hours Crew and employees were nice Extra long flight but at least we got in

The flight was delayed at the very last minute and no information, both of my round trip flights were delayed at least the BNA to Boston was informed earlier but the return one was horrible

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.

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Flight delayed and then cancelled (due to mechanical issues + weather). Poor communication. No one there to help with rebooking and accommodations for the night we had to stay in Newark. Our luggage was taken off the original flight and apparently left on the tarmac in the rain. Items were soaking rain. The following day, the flight was also delayed due to mechanical issues. The second year in a row that I had to sleep in an airport flying from Tokyo to Newark due to mechanical issues compounded by bad weather. Partly bad luck and partly just poor service.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

I did bought anything… I don’t understand how this book appears to me . Ridiculous

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.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

Our flight was delayed to Louisville. What made this worse was they did not have another flight attendant to service the flight. This caused an even longer delay. Then when a flight attendant did show up, she chose to "swap" flights with another flight attendant. Therefore, we had to wait longer for the other flight attendant to come to our flight. This is information that the gate attendant should not have shared. Processes and execution at American are broken. Passengers are feeling it. Fixing this starts at the top of the organization.

Both the gate agent and flight crew did a horrible job of expediting the boarding process. It was simply miss managed. The airplane was late to Tampa. Therefore, they should have expedited the de-boarding process and also boarding process. This did not happen and caused me to miss my connection. I ended up with a 7 hour hour layover just to get home. The overall flying experience on American has simply been degraded. On-time performance is a real problem every single week. This has caused me to consider moving my loyalty to an airline that has better performance metrics.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports