$150 Find Cheap Flights from Des Moines to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Des Moines to Caribbean Islands departing on 8/31. 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
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Des Moines to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$477
Santo Domingo
Santo Domingo2 stops$634
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$614
Nassau
Nassau1 stop$579
Kingston
Kingston2 stops$757
Simpson Bay
Simpson Bay2 stops$656
Providenciales
Providenciales1 stop$685
Port of Spain
Port of Spain2 stops$620
George Town
George Town2 stops$599
Aguadilla
Aguadilla2 stops$586
Punta Cana
Punta Cana2 stops$477
Santo Domingo
Santo Domingo2 stops$634
Montego Bay
Montego Bay1 stop$392
Oranjestad
Oranjestad2 stops$614
Nassau
Nassau1 stop$579
Kingston
Kingston2 stops$757
Simpson Bay
Simpson Bay2 stops$656
Providenciales
Providenciales1 stop$685
Port of Spain
Port of Spain2 stops$620
George Town
George Town2 stops$599
Aguadilla
Aguadilla2 stops$586

Book Cheap Des Moines to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Des Moines to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Des Moines to Caribbean Islands

Sun, Sep 20 - Thu, Sep 24
Multiple Airlines Logo
1:58 pm - 11:50 pm
DSM
-
SJU
8h 52m
1 stop
Multiple Airlines Logo
6:15 am - 7:57 pm
SJU
-
DSM
14h 42m
1 stop
$265Multiple Airlines
Thu, Sep 10 - Wed, Sep 16
Multiple Airlines Logo
1:58 pm - 5:48 pm
DSM
-
SJU
26h 50m
1 stop
Multiple Airlines Logo
12:59 am - 7:57 pm
SJU
-
DSM
19h 58m
1 stop
$266Multiple Airlines
Thu, Sep 10 - Thu, Sep 17
Southwest Logo
5:40 am - 8:05 pm
DSM
-
SJU
13h 25m
2 stops
Southwest Logo
8:55 pm - 11:25 am
SJU
-
DSM
15h 30m
2 stops
$376Southwest
Thu, Oct 15 - Mon, Oct 19
Southwest Logo
7:10 pm - 9:20 am
DSM
-
SJU
13h 10m
2 stops
Southwest Logo
10:50 pm - 11:30 am
SJU
-
DSM
13h 40m
2 stops
$388Southwest
Wed, Dec 2 - Wed, Dec 9
United Airlines Logo
6:15 am - 1:46 pm
DSM
-
MBJ
6h 31m
1 stop
United Airlines Logo
2:48 pm - 9:17 pm
MBJ
-
DSM
7h 29m
1 stop
$392United Airlines
Sat, Sep 5 - Sat, Sep 12
American Airlines Logo
7:56 pm - 1:12 pm
DSM
-
MBJ
17h 16m
1 stop
American Airlines Logo
5:16 pm - 8:39 am
MBJ
-
DSM
15h 23m
2 stops
$396American Airlines
Fri, Oct 30 - Sat, Nov 7
United Airlines Logo
6:05 am - 12:48 pm
DSM
-
MBJ
6h 43m
1 stop
United Airlines Logo
3:45 pm - 10:26 am
MBJ
-
DSM
19h 41m
2 stops
$397United Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
1:09 pm - 2:23 pm
DSM
-
MBJ
25h 14m
1 stop
American Airlines Logo
12:47 pm - 11:25 pm
MBJ
-
DSM
10h 38m
1 stop
$400American Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
5:40 am - 1:49 pm
DSM
-
NAS
7h 09m
1 stop
Delta Logo
1:16 pm - 10:34 pm
NAS
-
DSM
10h 18m
1 stop
$586Delta
Tue, Oct 20 - Tue, Oct 27
Delta Logo
5:40 am - 1:49 pm
DSM
-
NAS
7h 09m
1 stop
Delta Logo
1:16 pm - 8:51 pm
NAS
-
DSM
8h 35m
2 stops
$590Delta
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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $342, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Des Moines to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Des Moines to Caribbean Islands is August, when tickets cost $649 (return) on average. On the other hand, the most expensive months are November and March, when the average cost of round-trip tickets is $781 and $771 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Des Moines to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

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

$150
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 10% increase in price.
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

 
See real verified KAYAK customer reviews for airlines flying from Des Moines to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 4228 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

2.0 MediocreChristopher, Jul 2026
DEN - SJC
Read more Southwest reviews

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

Flight team was great and we even arrived ahead of plan!

It was good delayed again but once on board the flight crew were very good the entertainment and wifi worked on this plane and we were offered snacks and drinks

The boarding agent guy in Lexington on 7/23 that boarded the flights to Atlanta is very rude for working in customer service. I know there were delays but he was dismissive rude and arrogant. Most native Kentucky residents are nice and very cordial he needs to eat a big ole piece of humble pie. I watched him be rude to several people and as much as he could of filled up a delayed flight to save you money and he was so rude to people it was ridiculous. Next no water or snacks on short flights is awful 1st you delay a flight then do not even offer water on the flight.. No thanks I like delta better but I travel ever week and to be treated like this might as well fly American at least they offer water and have better rewards.

Flight was delayed multiple time and for more than 1 hr. My onward flight from BOS to MCI was also delayed. These delays have caused me so much inconvenience and Delta does nothing to ensure flights take off on time. No one knew why the inbound flight was delayed and what was the issue.

The second half of terminal C at Hartsfield was 80 something degrees. I was sweating just sitting at the gate.

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.

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

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.

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

Worst communication. Delayed boarding for two hours without a single announcement until hour 1 had passed - on time status showing until our flight was supposed to takeoff and the crew had already walked away. No one was boarding. Disgusting part of DFW overcrowded with no AC on a 97 degree day. Then the first app update is that we’d take off in 15 mins… but again no one had boarded a full flight. No announcement in the terminal so everyone is just crowded around a disgusting place with no info for over an hour which turned into two. This was an overfill flight and a disgrace to passenger decency all while likely just trying to fix their own issue of overbooking. The worst airline at the worst airport.

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