Find cheap flights from Aspen to Caribbean Islands

Find cheap flights from Aspen to Caribbean Islands

Round-trip
Economy
Aspen (ASE)
Caribbean Islands
Fri 1/15
Fri 1/22
Any month
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Top tips for finding cheap flights to Caribbean Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to Caribbean Islands is August.
  • Morning departure is around 65% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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Top airlines flying Aspen Pitkin County to Caribbean Islands

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,043 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

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!"

Pros: "Not much"
Cons: "Not sitting on the runway for 2 hours"

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: "Reliability that your flight will not be cancelled. Punctuality."
Cons: "They charge you $125 for a dog in cabin (JetBlue and Southwest near $100, Frontier $75). There is NO benefit, even with this extra amount of money. I was assigned to enter the aircraft in Group 8... I suggest AA the benefit to enter (at least) in Group 5 for people with PAID in cabin dogs."

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

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: "When we arrived at the Aspen airport, American Airlines was having a complete breakdown checking-in passengers for our flight. Some waited 2.5 hours to check a bag -- at an airport with very few flights and small planes. Clearly there was no management onsite – or that management was completely inept. AA agents on the ground simply did not prioritize passengers trying to make flights, nor did they ask flyers without urgent issues if they could step aside. Even worse, they spent 1.5 hours helping one customer – when that customer simply could have gone online or called reservations to get the appropriate assistance. Honestly, I personally stepped in to do what your personnel should have been trained to do: show empathy to calm passengers, ask one irate man to have some sympathy for those behind him in line, and finally, prioritize the people trying to check bags for the 2pm flight ahead of others. AA personnel only engaged the irate customer and threatened to call security when he pulled out his camera phone – it simply inflamed an already bad situation."

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: "USB Outlets are nice to have"
Cons: "Nothing was bad on this flight"

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

Pros: "Schedule was punctual. The entertainment was superb. Good crew. The overhead bins were, for some reason, larger which aided the boarding process."
Cons: "I guess the lack of snack options but that is just the way it is nowadays."

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!!!"

Pros: "The new clean plane. The pilot and crew were great."
Cons: "Nothing"

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: "The pilot was a riot, the flight was on time. Again, nothing wrong, nothing special. As it should be (if only we had more leg and seat room, and I am pretty streamline)."

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: "Nothing"
Cons: "Super old planes, no had a tv."

Pros: "Puntuality"

Pros: "The entire plane crew to the ground crew did their best with a situation that was out of their control. The luggage door would not close, so we had an apps 4 hour delay"
Cons: "All good."

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: "Nothing. My fight from San Juan to Miami on Friday Oct. 7 was cancelled because of hurricane Matthews, since I didnot buy a roundtrip with AA they did not reimburse or offer me a credit for my returning flight. I contacted AA in two ocassions and both times their personnel were impersonal and even rude to me with the whole situation. I ended up losing $250 because of choosing American Airlines. I will do my best to avoid traveling with American ever again, and I will spread the word, as well. I felt robbed, so unfair."
Cons: "Everything"

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

Cons: "No have owned screen TV"

Pros: "Even when the plane was full they managed to help passengers to get seated."
Cons: "If you still flying economy class, why would you have to pay extra for exit row where the seats are the same. Only received pretzel and a cup of drink on a 3 hour flight once."

Cons: "American canceled my original itinerary on direct flight to Los Angeles and put me on a flight to Dallas, Dallas to LA, and charged me for the change. After 8 hour delay at airport (boarding plane, on the runway) they turned us around and flight was delayed to the next day. I luckily got a direct on United and will avoid American at all costs."

Pros: "Everything"
Cons: "Nothing"

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

Cons: "One hour delay sitting inside the plane with no pilot!! And to top it off, the air conditioner was off!! Will never fly American ever again."

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

Cons: "I didn't like the American airline people who checked my bag. She threw it because I told her nothing was breakable in it."

Cons: "Gg"

Pros: "Great service. New aircraft. Lots of legroom. Great crew."
Cons: "None."

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: "The great atendance and on time bording"
Cons: "There is no More options of free food included with the ticket fly and it was a longer flight and there wasn't no tv, no entertament"

Pros: "My window seat was all."
Cons: "I didn't get a call about the delay like other passengers, only an email at 7am as I was in line to check in for the 8:25am flight 395. The female crew members, a dark haired woman and a short blond haired woman both would have ignored me if the other two people seated by me did not also try to get their attention. The dark haired woman gave the guy next to me headphones and when I held out my hand she just looked at me and walked away as if she'd been called away. Which she hadn't she came back and started with the row immediately behind us and the guy next to me was nice enough to give me his. Also after nearly waiting 4 hours, 9 minutes before boarding we were given food vouchers and told to "run and hurry" and get food "to go" so most people didn't even bother using the vouchers because of that. I've had better flights with American Airlines, I just didn't know this one would be so poor. Definitely way below average expectations."

Cons: "No outlets or entertainment"

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: "Nothing really. I'm glad Delta, Virgin, and Southwest have direct flies now so I don't have to deal with the worst airline in the history of humanity,"
Cons: "The worst support and irresponsible system canceling my seat and no support"

Pros: "Services , on time"

Pros: "Lady at the main customer service was trying to be very helpful.."
Cons: "Bording time ended at 10:00.. plane was departing at 10:15. Got there at 10:06.. the counter lady was very rude and instead of help me get to another flight or show me other options, she told me the doors was closed and that it was totally my fault I lost my flight since my prior flight got there early.. doors should be hold ten minutes after the end of the bording time. she sent me to the main customer counter.."

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

Cons: "See above."

Pros: "Seat more comfortable and any entertainment."
Cons: "The seat."

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."

Cons: "Delay?????"

Pros: "Food was ok"
Cons: "You don't have any free entertainment not even free music!!!"

Pros: "They gave me something to drink..."
Cons: "Didn't give us peanuts or any snack items and everything else had to be paid for which I think the pricing on those items were expensive that is abusive unacceptable and me as a military personnel I think there should be some kind of consideration in all those matters including paying for luggage $25..."

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

Pros: "Very nice breakfast provided. Staff was great."
Cons: "No media entertainment for 3.5 hour flight"

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

Cons: "The flight was life threatning. The pilot hit a patch of air, and there was screaming and people were hysterical. Honesty, we thought the plane was going down into the water. I still have not recovered from the fright, and i dont know how i am going to get back on ghe plane to go home. Thr captain didnt even address the issue or appologize for the discomfort. Very unsatisfied...and scared. I left 7 small chikdren at bome, who all need a mother."

Pros: "Estaba supuesto ser un viaje barato y puntual"
Cons: "Pero no fue de esa manera yo soy un paciente esquizofrénico y padezco de vipolarida más tengo problema con el azúcar mas padezco de sleeping adnnea.y muchas otras condiciones.y mi vuelo no salió cuando. Tenía que salir.yo vivo en perth ambos y era muy difícil viajar para Mi en tren para luego tener que pasar todo lo que pase.deverian por lo menos recomendarme con algo desierta por todos mis inconvenientes."

Pros: "Free blankets for the long flight."
Cons: "Worst landing I've ever experienced on a plane. Had whiplash that gave me neck pains for several days after."

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: "I very much enjoyed the male flight attendant in coach. He was fun, attentive and very interacting."
Cons: "I liked all but the seating. Even for coach is too small in my opinion. Pilot flew awesome."

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

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: "pleasant staff at terminal"
Cons: "notified at absolute last minute that flight was canceled with no weather related cause. Airline knew ahead of time as aircraft did not arrive. poor communication overall."

Pros: "Nothing"
Cons: "United cancelled my flight. Terrible customer service"

Pros: "The service & how comfortable I was."
Cons: "That you have to pay for everything but I guess now a days every airline is doing the same thing."

Pros: "Great in flight service. On time. Easy upgrades using United mobile app."

Pros: "Flight attendants were nice."
Cons: "On LAX tarmac for 40 min. Food awful"

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

Pros: "Love the crew!"

Cons: "The delays was horrible!!"

Pros: "Rate was very good and the time of the flight was perfect! Non-stop and all."

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: "United personal quickly found our bag location and made the arraingement to send it to us ASAP."
Cons: "The fact that the only bag we checked in with the airline did not arrived in our plane with out any warning what so ever."

Pros: "On time, friendly crew and very reliable"
Cons: "Where's the food?? Gas prices have dropped significantly but all airlines still skimp on food, charge for bags and tickets are still pricey"

Cons: "It took to long to board the flight"

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: "The United App is a must. Having so many movie and tv options made the flight breeze by."
Cons: "The cabin was so uncomfortably hot. After passing by a second time with the drink cart, there was still another two hours left on our 4.5 hour flight. I hit the button to request a flight attendant, and after 15 minutes, one finally answered. I asked for water, and they stood over me while I drank it so they could trash the cup."

Pros: "Good trip"
Cons: "Nothing"

Pros: "The crew kept us feeling comfortable"
Cons: "Hated the security check in on the airport because of their lack of staff also hatted the flight we were delayed 3 hours"

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: "Boarding process on time."
Cons: "The waiting time for my connection flight."

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

Pros: "Very punctual, arrived before time to connecting flight. All great"

Pros: "Everything was great"
Cons: "Nothing"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Aspen to Caribbean Islands

Airlines flying from Aspen 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 Aspen to Caribbean Islands

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Aspen to Caribbean Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Aspen to Caribbean Islands

Book cheap flights from Aspen to Caribbean Islands

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