Find cheap flights from South Dakota to Caribbean Islands

Find cheap flights from South Dakota to Caribbean Islands

Search hundreds of travel sites at once for deals on flights to Caribbean Islands

Round-trip
Economy
Boston (BOS)
Caribbean Islands
Thu 4/15
Thu 4/22
Any month
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Good to know

Low season

AugustBest time to beat the crowds with an average 5% drop in price.

High season

DecemberMost popular time to fly with an average 13% increase in price.

Average price round-trip

$395(avg. price over the last 2 weeks)

Good deal round-trip

$128or less

Good deal one-way

$72or less

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Top 3 airlines serving from South Dakota to Caribbean Islands

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,374 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.9
Entertainment
6.7
Food
Airline reviews

Pros: "The price."
Cons: "Flight was delayed for 2 hours in Airbus 777 full of passengers. The reason was to fix some light and administrative error on a log book. This could have been prevented if they had done all of the checks beforehand. All of those passengers stuck in a plane during a pandemic. Not very smart !!!!"

Pros: "On time take off and the fact that we arrived alive."
Cons: "Hot meals and inflight entertainment. No even drinks were served."

Pros: "Great service and comfortable; well sanitized."
Cons: "TV screens for movies and shows."

Cons: "American airlines oversold and that caused us to start late. The seats are too small for 2 adults to sit next to each other. 1/2 the people wore masks. when we arrived we sat on the taxiway for an hour"

Pros: "Lounge was nice at DFW"
Cons: "American Airlines alone received over $10 billion in COVID relief, yet they are steadfast on a policy that separates customers on the same reservation (basic economy). $$$ over health & safety. Other airlines are leaving the middle row empty while AA wants a second bailout from Congress. Shameful!"

Cons: "Some of the crew had an attitude and the purchased WiFi did not work"

Cons: "Almost 4 hour delay."

Pros: "Crew was snappy in getting people in plane and checking in carry ons since occupancy had been reached."
Cons: "Lack of adjustable headrest on seat."

Pros: "Smooth ride"

Cons: "Feeling of being cramped"

Pros: "Crew was great!"

Cons: "Todo bien"

Pros: "Service from crew was fine"
Cons: "No delay! Got notification that our flight was one half hour earlier. Then boarded aircraft, and it had electrical problems. Delayed. We had to get off. Then board another aircraft."

Pros: "Checking in with my Mum who needs assistance was excellent."
Cons: "Lack of Entertainment."

Cons: "Crampt space, cold cabin"

Pros: "None"
Cons: "Long delay"

Pros: "Movie options were good."
Cons: "The a/c was not working well and t"

Pros: "The service was excellent and the flight on time. Love American."
Cons: "The seats have been refurbished and if you are a plus size the seats are uncomfortable."

Pros: "Service"
Cons: "Seats and space"

Pros: "Turkey sandwich snd boarding went smoothly"
Cons: "There was no entertainment and since there is no WiFi for most of the flight due to being over water the flight seemed longer than what it actually was."

Cons: "Poor service"

Pros: "I loved everything. No complaints. American airlines is one of the best airlines I have flown with."

Pros: "I liked that we got to San Juan safely. The crew on board was very accommodating."
Cons: "Due to the delays, we missed our jumper flight and American refused to compensate. Also, only had two cookies all day from 8:05am until 3:45 pm! No sandwiches as promised. We were delayed approximately 4 hours total. Had to take a taxi ($85) to Fajardo to HOPEFULLY catch last ferry to Culebra. Guess AmericansAirlines doesn’t care if you have to sleep at the dock!"

Cons: "Dallas to San Juan San Juan Dallas American Airlines has the worst seat of any airline flown by us fare almost 2000 dollars for round trip and the seat is small hard uncomfortable even for a short flight this is no business class!!"

Pros: "On time"
Cons: "Cold cabin"

Cons: "The seats are very tight."

Cons: "Last minute cancellation and reschedule if original flight with 20 people hounding the gate for standby status. Craziness. These last minute revisions mist stop"

Pros: "Direct flight"
Cons: "Horrible customer service, excessive baggage fees, rude counter staff, no leg room, narrow seats"

Pros: "Boarding process"
Cons: "Delay, no food,"

Pros: "Can't think of anything good"
Cons: "SEE: Customer Relations request #1-249830721"

Pros: "Nice crew clean airplane"
Cons: "Initial flight was cancelled after 2 hours delay. My next flight was scheduled the earliest possible by AA which was 24 hours later. No transportation,hotel or miles compensation for this. I had work and responsabilities the next day. TThe scheduled trip was supposed to take off at 7:45. Boarding started late and was very slow. My bag fit the meassurements and still was forced to check it (which I did not want to do as I did not want to be waiting an hour for my bag at my arrival as I had work early the next day. In addition there was airplaine traffic as it was "rush hour" instead of flying at 7:45 we departed almost at 9pm!!!! Have to pay for food Quality of tv monitors very poor And in an uncomfortable position No movie options No wifi although stated the aircraft has Non functioning electrical plug"

Pros: "Nothing"
Cons: "Never made it to San Juan to catch my cruise. To top things off I was a ship for two days without my luggage and underwears. Never again!!! Thank you JetBlue!!!"

Cons: "That all the passengers were rechecked at the Gate by TSA without offering any explanation as to why, if it was a domestic flight, why were they requiring ID again. And checking bags."

Pros: "On time smooth"

Pros: "Friendly staff. Landed early. Offered a free bag."
Cons: "They moved the flight earlier, which was not fun. And, there were no entertainment centers."

Pros: "Puntuality"

Cons: "There seets are two small. And they dont sell alcohol. That sucks."

Cons: "The airline had trouble with the plane. After we waited 3 hrs in the plane they cancel the flight. They offer a hotel but it was very dirty"

Pros: "Friendly polite staff. Plane left and arrived on time."

Cons: "No have owned screen TV"

Pros: "Everything"
Cons: "Nothing"

Pros: "Comfortable seat"
Cons: "Lack of entertainment"

Pros: "Overall good flight"
Cons: "I did not like the time needed for boarding/ settling in. But that is a factor of people not following instructions. Not the crew."

Cons: "Terrible airport assistance, many unnecessary customs checks, uncomfortable seats, on flight bad service and late flight times."

Pros: "I was going home"
Cons: "Late flight no pilots andt broke my luggage."

Cons: "Gg"

Pros: "Everything was on time, no delays."

Pros: "Should have individual tv's like jet blue does. There shoul be a family travel area for people travelin with todlers. better service and better food. Faster luggage pick up."
Cons: "Nothing. Expesive flights, an unprofessional flight attendant name Sarah, fighting with the customers. No entertainment. It was a nightmare"

Pros: "I live the service which make me feel good. Also the flight was very quiet and the crew help me in everything I asked."

Pros: "Nothing"
Cons: "Not having so many delay and not seating on a plane for over an hour to take off."

Pros: "Friendly crew"
Cons: "Leaving crying babies at home..."

Pros: "Weather delays and the Boeing 737 problems a little out of their control. Some things could have done better, but some good employee efforts."
Cons: "Small planes are subpar.. Food useless. Baggage fees. When things go bad you're on your own."

Pros: "Nothing"
Cons: "Plane on time and it was very hot on the plane"

Cons: "Again, left stranded in SC."

Cons: "If this flight had been delayed to match our flight from AUS. We arrived in SJC at 1100. So a 8 hour extra time in flight was avoidable if United had waited 30 minutes."

Cons: "Nothing"

Pros: "Nothing, The flight didn't happen"
Cons: "Waited for 6.5 hours for the flight to get cancelled and rescheduled for a week later."

Pros: "Crew was very nice"
Cons: "Sits are very uncomfortable"

Pros: "Just what I needed, right when nothing was working out. I had many things going on in my mind, yet nothing had to do with my flight. Everything worked out perfectly after all."
Cons: "When we arrived in PR there wasn't a gate available because the one that was assigned had a broken jet bridge."

Pros: "Getting home safely!!"

Pros: "All in the prices!!! Accesibility!!!"
Cons: "The prices changes too much!"

Pros: "Nothing"
Cons: "I'm supposed to bring a carry on with me and they don't allowed me this time. They should be strict with other passengers who bring more than a carry on. I was SO MADDD"

Cons: "we took off over 1 hour late"

Pros: "Services , on time"

Pros: "All the way we had a great atencion from all the crew and airport facility thanks"

Cons: "See above."

Pros: "-United employee upgraded me to Business Class at no extra cost. She was extremely nice."
Cons: "They had multiple passengers on a standby list waiting to board the already crowded flight. Plus, had numerous people without a seat assigned while offering them a $250 travel credit to get off the plane."

Pros: "Great service, it had been a while since I flew with United. Impressed with the new plane."

Pros: "clean; good movies"
Cons: "no kosher food option"

Pros: "On time and comfort"

Pros: "Smooth boarding"
Cons: "No entertainment of any sort available unless paying."

Cons: "My seat was the last line and it was uncomfortable."

Pros: "It was a good flight. The attendants were courteous and accomodating. There was nothing to complain about."

Pros: "That i had all four seat available to me and very helpful"

Pros: "Was fast and on time"
Cons: "Pushing back from gate took for ever due to mechanical problems and somebody got sick on the plane so their decision to wait until the person situation got better affected everyone else"

Cons: "Since united took over food court it is impossible to get breakfast. 30 minute wait at the kiosks, missing items at express, no coffee at Stromboli stand, another line to get coffee. 8:30 flight pulls out on time but doesn't leave for another 45 minutes, still posts as leaving on time."

Pros: "very helpful"

Pros: "That we didn't crash."

Cons: "Thr boarding process was a mess, a lot of people didn't even have seats assigned."

Pros: "The personal are very amability"

Cons: "The delays was horrible!!"

Pros: "Fast and easy boarding"
Cons: "No tv, no , no magazines"

Cons: "I missed my second flight by 10 minutes due to a delay from my first flight and was only refunded a small portion luckily I found a good price with Jet Blue wich worked out better"

Pros: "The staff was very helpful. When overhead storage was full, bags were checked at no additional cost."
Cons: "Had trouble with the highly advertised entertainment. On the trip from Rapid to Chicago, the entertainment wouldn't work. I was fairly comfortable in my aisle seat, but think it I had to be in a center of window seat, I would have been very uncomfortable."

Pros: "Boarding"
Cons: "Excellent"

Pros: "The service since I am handicap"

Pros: "Fantastic service"

Cons: "Comfortable and affordable!"

Pros: "I liked when I got home 12 plus hours later than I was supposed to!"
Cons: "The three canceled flights and 7 delays that I was out through were awful!"

Pros: "What I like the most was that it was on time, also the crew was amicable."

Pros: "Very organized . On time"

Pros: "Everything! My grandparents needed special assistance with wheelchair and the crew was very helpful! They spoke Spanish and they were able to get a crew member to translate"

Cons: "Last row seats. Nothing of space, man seating next to me in the isle seat couldn't accomodate his legs inside the available space."

Pros: "Good trip"
Cons: "Nothing"

Pros: "My flight was rescheduled so I hope I did not get charged for another flight."

Cons: "I never took this flight since the San Francisco flight got delayed that when I got to the gate to board the Washington flight. The gates closed on my face literally. Awesome trip.! (Sarcasm included)"

Cons: "They did not have TV and no wifi it was terrible. They only gave me a cup of soda nos even a potato chips which other airline do give."

Pros: "Getting from point a to point b."
Cons: "Lack of good free snacks. Not getting free bag checked."

Cons: "Pilots capabiliy. Excellent smooth landing. Friendly crew."

Pros: "Efficient"
Cons: "Plane was very late"

Pros: "Very quick flight, 45 min early"
Cons: "Cheaper baggage and free drink"

Pros: "Liked the price"
Cons: "Choice of seating if available."

Cons: "It really ridiculous to advertise as a cheap flight but in the end they change for everything."

Pros: "Great seats (row 3 upgrade), smooth uneventful flight"
Cons: "Extra charges for everything: seats, carryons, basic beverages. $38 for carryon or checked bag is over the top. $3 for basic drink that is comp on other airlines. No snack, even basic pretzels."

Pros: "The crew tried to make the delays suck less."
Cons: "Delays. Delays. Delays. And no communication with passengers. Flight boards were incorrect and the only information I could get was from the desk."

Pros: "The price"
Cons: "I showed up 50 minutes before boarding due to traffic and they wouldn't check my bags, said I had to be there 2 hrs before with no solution. Did not give me a refund either :( the flight also ended up being delayed an hour and they still didn't let me through."

Cons: "The plane was very hot"

Pros: "Our flight was delayed and the crew was very nice and took great care of us"

Pros: "I FINALLY arrived at my destination."
Cons: "Huge delay, no explanation. Cabin filthy."

Pros: "The crew were nice."
Cons: "Nickel and dime you for everything. Not even water was offered on the flight. The seats were the worst on any airline I have flown."

Cons: "The scheduled plane had a mechanical problem so we deplaned for alternative plan. It took six long hours to get another plane in. Meantime passengers stood in line for hours to make other arrangements. It would have been appropriate for the airline to call in extra staff to help stranded passengers. We missed the scheduled connecting flight and a tour. We got in at 1:00 am, 12 hours later than planned. We had meetings next day and were very tired because we got in so late"

Pros: "Got me to my destination. Made my connection. What was the entertainment?"
Cons: "Lack of complimentary beverages. High charge for checked luggage & carry on luggage. Too many additional charges. Enjoyed flying with other carriers better with amenities with cost equal to or less than cost to fly Frontier. Late departure."

Cons: "Overall"

Pros: "The seats were designed by a sadist"
Cons: "Seats not suitable for anyone other than a hobbit"

Cons: "Customer service is extremely poor and non existant and NO help whatsoever to accommodate for another flight. NOTHING."

Cons: "Most uncomfortable seats"

Pros: "Flight attendants were great and can't beat the price!"
Cons: "Flight was delayed for over 2 hours and did not once get an update from frontier staff on what was going on...nor did they apologize for the delay when we finally boarded."

Cons: "extra baggage fees for a single carry-on & having to pay $5 to choose my seat after already buying a ticket---price was not what initially seemed to be"

Pros: "Ticket price was ok"
Cons: "Delayed flight, tiny space under seat for bag, extra cost for carry-on not known until check-in was not ok"

Pros: "Shitty cut rate airline. Never again. Kayak or Frontier."

Cons: "Overall it was goo. The flight was delayed"

Pros: "Typical flight service (which is better than I was expecting), staff was friendly and seemed helpful"
Cons: "Taxi'ing for about 15 min one landing, getting hit with carry-on fees while checking-in, probably would not fly with them again unless I was packing very light, otherwise you should just go with a larger airline and not risk flight cancellations/delays/runway taxi."

Pros: "The counter person was nice & did a good job of giving us our options DUE TO FRONTIER CANCELING THE FLIGHT."
Cons: "I was told that Frontier could not help us find another airline and that the soonest they could get me on another flight was 5 DAYS. I was told if I could find another airline on my own that FRONTIER WOULD REFUND THE TICKET PRICE SINCE I DID NOTHING WRONG. I submitted for a refund and was denied the refund. WTF frontier whats going on??"

Pros: "Not much at all"
Cons: "Flight was four hours late despite being listed as"on time" Took over an hour to get off the plane after we landed. No updates given."

Pros: "price"
Cons: "no snacks, fees for carry ons as well as $40 per checked bag"

Pros: "Atleast they fly to Souix Falls"
Cons: "They closed the check in area 45 min. Before flight, thankfully everything was on our phones and it's a small airport so the TSA got us through so we could Chek in at the gate. 3+ hour delay for "maintenance issues" (found out it was a paperwork issue the plain was fine the whole time). We boarded, then after an hour we were let off the plain to go to the bar, which was closed but they reopened for us, but no food. We were starting to figure out if we needed to rent a car before the rental places closed. Finally got back on the plain, and got to Denver. Frontier send an apology letter with a 50 dollar credit, we spent more at the bar while we were waiting. Frontier is only good for last minute cheap flights then they nickel and dime you to death. Their customer service sucks, the last time I was on Southwest with a delayed flight, (only about an hour late and the plain was late coming into Denver) they gave us a 200 dollar voucher right then and there, apologized a ton, and gave anyone over 21 a free drink. I'll be sticking with southwest even if it cost a little more!"

Cons: "Rescheduledo my flight to Phoenix by 12 hours. Then on my way back to Indianapolis from Denver there were 3 gate changes and then an hour delay"

Pros: "Reasonable fare. Retractable armrests. Flight attendant gave fistbumps. Cylindrical ice cubes-easy to chew. Pilots handled turbulence 'like a boss!'. Aircraft made excellent 'VROOM' noise on take off. Staff loading checked baggage into aircraft waved and smiled at me."
Cons: "Paying $30 for one carry-on bag? Ouch. Snacks were a trite pricey. Flight was ~70 minutes, tushy and lower back was uncomfortable in seat. Lack of magma in lavatory (get it? LAVA-tory?)"

Pros: "Boarding was quick and smooth"
Cons: "Entertainment: there was none."

Cons: "Well first our flight got delayed an hour and a half and then delayed another couple hours and then finally the flight was flat out cancelled till the next day which made us obviously miss our flight to portland that night and we had emergency prior engagements that we missed and a whole weekend we paid for that is now missed because we won't be getting to Portland until practically two days later assuming everything goes perfectly today. ( currently sitting in Sioux Falls airport)"

Cons: "The 5 minute frontier credit card flight attendant commercial has got to go."

Pros: "I had a problem when I was printing my ticket. I called Frontier about the problem. They fixed the error, waived the extra fee and as long as she had me on the phone she walked me through the rest of my check in. When I got to the airport the staff at the Frontier counters were very friendly and courteous. The flight attendants were also upbeat and good with the passengers."

Pros: "About the only good thing I have to say about this flight was that the pilot was good about communicating what was going on as a result of bad weather in the area of our destination."
Cons: "Overall the Frontier staff was not helpful. They had no information and didn't really seem to care. The flight attendants were doing the bare minimum. And when asked a question they were not helpful and also didn't seem to care about the comfort of the passengers. Several of the overhead lamps on this plane were out. Even though we had to wait on the plane for over an hour before departing, no drinks were offered (unless you wanted to pay for them). I think there are things that can be done to make an experience more enjoyable even when things are not great. Like offering a free soft drink to passengers as they wait etc. Being cheerful can go a long way, and we weren't getting that from this Frontier crew."

Pros: "No food was served on the plane"

Cons: "I did not realize they charge extra money for a carry-on bag. At that point you have no choice to pay the money. That should be noted up front."

Cons: "We had to wait ONE HOUR AND FIFTEEN MIN FOR OUR BAGS"

Cons: "The staff is rude first and foremost. I flew from Austin to Denver and once we landed in Denver we had to sit in our seats for over an hour until we're finally released from the plane. My flight from Denver to San Diego was 35 minutes late and once I arrived to San Diego my checked bag was lost. I am still waiting for the search team to find my bag with all my clothes. If you like poor service , Rude staff, and unprofessional people then this airline is perfect for you"

Pros: "Non stop"
Cons: "Packed in like sardines....add on costs"

Pros: "rally expenser the food"

Cons: "There was no food or entertainment so I could not make a judgement on these. With a short flight it is not needed."

Pros: "The crew was friendly, and conscientious. They had an excellent attitude."
Cons: "I'm 6'1", do you really need that 4" of knee room?"

Cons: "Have to pay for water,ridiculous!"

Cons: "I had to stay overnight in Denver, in the waiting area."

Pros: "Frontier refunded my entire trip."
Cons: "As others have mentioned, they slapped on very deceptive fees at the last minute for things that no other airline charges for like choosing a seat assignment and a carry-on bag. The fees completely negated any savings from booking with them in the first place. Also, the online check-in system was clunky and took longer than it should have, and then my flight was cancelled because they couldn't get their act together with scheduling two days after a storm hit Denver. I had to re-book my flight with another carrier which ended up costing $1200. Not a bargain!"

Pros: "Nothing"
Cons: "Start with paying for a carry-on, which made this "cheap" flight as expensive as a better airline. And paying for a seat assignment?! Didn't get a chance to experience paying for water onboard, as the entire flight was cancelled. Thanks to their lack of connection to other airlines, they couldn't get us where we were going prior to our RETURN date. So our lodging, car rental, etc all were completely wasted, at our expense - no vacation, but still had to pay for it. "Nothing we can do, sorry, it's the weather..." Really?! Weather explains a delay, not torpedoing the entire vacation. This airline is the absolute pits."

Pros: "The plane didnt crash and for once frontier wqw actually on time"
Cons: "Frontier went from being a great airline to nickle and dime air. There was a fee for EVERYTHING. $40 for carry on luggage?! Tlwhat a joke. A bag that i carey and hanfle myself does not constutue a $40 fee. Hell the bag didnt even cost that much. Not to mention the hard back cattle seating they installed plus charging for water. I will never fly frontier again after 20 years of flying with them."

Cons: "A family of 4 with 2 small children sat behind my colleague and I on a 6:30am flight from ATL to LGA. There were 2 small children who disrupted my entire flight. Constant banging on the back of our chairs, slapping the trays up and down for 2 hours, slapping the plane windows, etc. After repeated efforts to ask the parents to have their children stop, the parents could care less about the disruptive behavior of their children. Complaints were made to the crew to no avail. The children were disrupting the entire 5 rows around them. These passengers should have paid for my and my colleagues flight, in addition to their flight, as they cause one of the worst experiences on a flight I've ever had. After this flight, I believe there should be a policy that if you have children on a plane, you should be required to pay more, allowing the people around you to pay less or opt out of having to be seated next to a passenger with a child."

Cons: "Flight leaving Sioux Falls was delayed, cutting into the time needed to make my connecting flight to Orange County (SNA). No reason given for delay, weather was good, all the west from Sioux Falls to Orange County."

Pros: "Crew was nice. Plane was crummy. Seats do not even recline. No in flight entertainment at all. You have to pay for any snack of any sort."

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from South Dakota to Caribbean Islands

Airlines flying from South Dakota to Caribbean Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from South Dakota to Caribbean Islands

Mandatory masks

Masks required on board, masks provided on flights from South Dakota to Caribbean Islands

Social distancing seating

Middle seats unavailable to book on flights from South Dakota to Caribbean Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from South Dakota to Caribbean Islands

Book cheap flights from South Dakota to Caribbean Islands

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