Find cheap flights from Aspen to Caribbean Islands

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

ASE — Caribbean Islands
Oct 29 — Nov 51
Round-trip
1 adult
Economy
0 bags
From?
To?
Sat 10/29
Sat 11/5

Let KAYAK do the searching

Save 20% or more

We’re completely free to use – no hidden charges or fees.

Filter by cabin class, free Wi-Fi and more

Bundle your flight + hotel and save

Top tips for finding cheap flights to Caribbean Islands

  • High season is considered to be January, February and December. The cheapest month to fly from Aspen is January.

FAQs - booking Caribbean Islands flights

Top airlines flying Aspen Pitkin County to Caribbean Islands

Scores according to KAYAK customer reviews
7.2
American AirlinesOverall score based on 48762 reviews
7.5Boarding
7.1Comfort
7.9Crew
6.9Entertainment
6.7Food
Airline reviews

Great flight overall. We boarded quickly and the flight attendants were happy and efficient. We sat on an exit row so plenty of room.

Read more about American Airlines

Great flight overall. We boarded quickly and the flight attendants were happy and efficient. We sat on an exit row so plenty of room.

I liked nothing about how my ticket was handled. I booked my flight through kayak. I sent my passport in for renewal 7 weeks ago. I waited until the last day Hoping I would receive it. I did not in time to make the flight. In order to rebook it would cost $500 more Than I already paid. I couldn't do that so I asked for a voucher. My refund was $90 out of the $1000 I already spent. I feel like I've been raped. Not only did I not make the trip I lost 90% of the money I paid for the ticket. Took me a year to save the money for the trip.

The flight was on time. The flight was rough/ choppy so there was no beverage service. The could of offered bottled water and the cookie or pretzels. Not customer oriented. Cleveland -Anerican Airlines needs to reorganize/ layout their incoming boarding pass and ticketing/bag tag area with a separate customer service area for flight cancelations. It is a cluster! Someone should video tape and send to the funniest video program.

Boarding process was fairly easy. Seats were slightly cramped but overall was fine. Departed on time and landed a little early too.

Our flight went off without a hitch.

Hassle waiting for bagged in walkway as t the we gate

Delayed over 6 hours for a mechanical issue. They had to fly mechanics in to fix the problem because there are none in Aspen. I feel like we should all get half off when this happens. Ridiculous.

Pros: "Flight on time and covid Prevention was in place."
Cons: "Failed to provide wheelchairs as requested."
Cons: "Sat on the runway for over an hour. Lack of communication and lies.."
Cons: "Plane had to land in a different city due to inclement weather. Very disorganized process, huge traveling setback, never got my travel voucher."
Cons: "Great flight"
Cons: "My charger port wasn't working for my phone, and the movie in wanted to watch wasn't working either."
Pros: "Crew members were okay"
Cons: "Wifi could be better"
Pros: "Very friendly and accommodating."
Cons: "tv screens on the back of seats"
Pros: "It was quick."
Cons: "The plane could have arrived on time, made sure everything worked fine, and got me to my destination like they said they were going to... instead, stand by for a different flight was not what I paid for... but it is what I got."
Pros: "Boarding was seamless, crew and flight attendants were awesome."
Cons: "The aircraft itself seemed dated. Very limited seat adjustment options, considering I was in First Class"
Pros: "Boarding was super easy. Great entertainment."
Cons: "Overall comfort. Space to relax."
Pros: "The crew was fantastic and very nicely got us into an earlier flight and allowed my wife and I to sit together for our 10th anniversary"
Cons: "The entertainment apps were difficult to use"
Pros: "Nice Crew. Very accommodating."
Cons: "The input for the headphones were not working properly at my seat location on the flight. Seat #10c on a A321 Airbus from Miami to L.A."
Pros: "WiFi entertainment system."
Cons: "Hard seats, no arm padding. No power to recharge phone and iPad."
Pros: "Not much"
Cons: "Not sitting on the runway for 2 hours"
Cons: "Crew was cold and rude"
Pros: "We got to our destination aver 12 hours late."
Cons: "In addition to being rebooked approximately 12 hours after our original flight, this flight left about 40 minutes late."
Cons: "I didn’t like to have 4 stops and so many hours of layover between all of my trips I will never ever buy a trip with a travel agency it is so complicated to make a change and they want to charge you about 5,000 dollars for a change! awfull!!! waitress from miami to london was not so nice."
Pros: "We arrived safely and so did our luggage."
Cons: "PHL-Lisbon plane left 3 hours late due to CATERING problem. Seats were uncomfortable and food was awful. Lights and entertainment controls at my seat didn’t work."
Pros: "Arrived slightly early. The crew was efficient and friendly. The interior and seats looked new."
Cons: "Nothing was negative."
Cons: "I am very frustrated that a single part could not be located in the early afternoon to allow the plane to fly. I will be late again for work and it seems to be American Airlines and not Delta that has all the delays or is late."
Cons: "The only problem that I had with my flight is that my luggage did not arrive on the same flight. Possibly due to my connecting flight from DCA to JFK. Both American Airlines and British Airways reassured me that it would be at Gatwick Airport when I arrived. Unfortunately, it did not. It took approximately four days to get my luggage. This was definitely a lessons learned."
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: "Coach seating is too tight"
Pros: "The free movies that are provided with the normal boarding passes is a huge plus that definitely comes in handy for longer flights. The staff did handle the delays very professionally and offered to help in any way possible"
Cons: "The flight received multiple displays before the plane landed then once it had landed it took the crew over an hour to decide that it was broken and that we would need to relocate to another plane."
Pros: "What a great plane with a great crew. Truly an enjoyable flight. And the tailwind got us in quite a bit early!"
Cons: "Boarding chaos at Miami airport."
Cons: "Either Webjet or BritishAir failed to notify our party in advance to allow a reasonable accommodation of our fully paid requirements."
Pros: "The new clean plane. The pilot and crew were great."
Cons: "Nothing"
Pros: "Overall the flight was good, on time"
Cons: "Nothing at this stage"
Cons: "I was very cramped in my seat."
Pros: "The gate agents did a good job of making sure the boarding process was organized, despite confusion with two Chicago-bound flights departing from the same gate in a short window. Delay was communicated far enough in advance that I didn't travel to the airport until it was necessary."
Cons: "The flight was delayed 3 hours due to the incoming aircraft, but nobody at the gate or onboard offered any explanation or even acknowledged the delay. The aircraft did not handle turbulence well at all... one of roughest flights in recent memory despite avoiding weather. Wifi had weak signal (on a 70-person jet!) and the streaming entertainment did not work the entire time... it either did not load or I got an error message."
Cons: "Was very stuffy and hot. Plane never cooled down."
Pros: "It was on time & staff were pleasant & effective"
Pros: "The Boarding Was Fast And Easy, The Flight Was Even Early And On Time! The Crew Was Very Nice."
Cons: "There Was No Entertainment For A Almost 2 Hr Flight."
Pros: "Same as above."
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: "My flight was cancelled and I never got an email notification so they made me fly to New York and the flight was delay. One of the ladies from New York was really rude to me."
Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"
Pros: "Boarding staff helped in rearranging seats on request"
Cons: "No snacks provided only beverages supplied"
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: "Entertainment was free."
Cons: "Had to wait for mechanical issues so we were delayed."
Pros: "Boarding was smooth. Flight was on time. Some weather en route but pilot was able to avoid the turbulence. Overall a good flight."
Cons: "Unrelated to the flight- but immigration and customs in Grand Cayman was slow. 200+ people arrived on this plane and there ware 4 immigration agents although they had more stations. We spent about a half hour in line in each- immigration and then customs. Rental cars is another situation to be aware of regarding insurance."
Pros: "Business class is very good"
Cons: "Economy seats on United are always incredibly uncomfortable, but the timing of the flight, and our on-time departure and Earley landing could not have been better. We will certainly fly United again on this route!"
Cons: "Food and rough flight"
Pros: "Crew was very nice!!"
Cons: "Space on seat not comfortable for tall people"
Cons: "Seats could have been better. Very uncomfortable seats"
Cons: "Again, left stranded in SC."
Pros: "OK"
Cons: "Probably nothing"
Pros: "The crew was helpful and nice."
Cons: "It was delayed a lot."
Pros: "Check in and departure very quick, efficient and professional.... very intuitive and helpful when observing that customer is in need"
Cons: "From a customer service standpoint, I Would lower or not charge business or first class rates on a jet in which the seats for the above mentioned clearly have no physical distinction from those in economy class. Just a thought."
Pros: "Service at business was good. Comfortable chairs and quiet cabin space."
Cons: "The gate experience due to long time between flights getting worst due to a departure delay."
Pros: "Comfortable seats with a touch screen with plenty to choose from to entertain. Updates from the cockpit often. Good music as we boarded and exited the plane to set the mood. Very attentive staff. Would love to fly with United again, soon."
Pros: "I wish travel miles automatically with my trip!"
Cons: "I didn't like to pay for my only registry luggage, i think that I would pay fo the second or more"
Pros: "I liked the perfect landing!!"
Pros: "When the lady in the gate saw me almost dying of running all over the airport with my suitcase, she was very nice and comfort me."
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"
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"
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"
Cons: "See above."
Pros: "Seat more comfortable and any entertainment."
Cons: "The seat."
Cons: "Delay?????"
Pros: "Friendly & informative captain & crew"
Cons: "Smooth flight, no complaints, A+"
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: "Smooth boarding"
Cons: "No entertainment of any sort available unless paying."
Cons: "My seat was the last line and it was uncomfortable."
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: "Lots of delay, not so friendly flight attendants"
Cons: "The baby crying!"
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: "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."
Cons: "Thr boarding process was a mess, a lot of people didn't even have seats assigned."
Pros: "The personal are very amability"
Pros: "Love the crew!"
Cons: "The delays was horrible!!"
Pros: "Fast and easy boarding"
Cons: "No tv, no , no magazines"
Pros: "Everything was perfect, the crew was fantastic"
Cons: "Maybe a bit of food."
Cons: "The airline is horrible.. Poor customer service"
Pros: "Boarding"
Cons: "Excellent"
Pros: "The service since I am handicap"
Pros: "Bien"
Cons: "Bien"
Pros: "Everything"
Cons: "Comfortable and affordable!"
Pros: "What I like the most was that it was on time, also the crew was amicable."
Pros: "Very organized . On time"
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"

Book cheap flights from Aspen to Caribbean Islands

Recent round-trip flight deals

10/29Sat
2 stopsAmerican Airlines
26h 00mASE-GCM
11/11Fri
2 stopsAmerican Airlines
24h 21mGCM-ASE
$485
3/12Sun
2 stopsAmerican Airlines
20h 06mASE-GCM
3/16Thu
2 stopsAmerican Airlines
20h 38mGCM-ASE
$675
10/28Fri
1 stopAmerican Airlines
24h 35mASE-GCM
11/11Fri
2 stopsAmerican Airlines
24h 21mGCM-ASE
$692
2/25Sat
2 stopsAmerican Airlines
18h 06mASE-GCM
3/3Fri
2 stopsAmerican Airlines
21h 55mGCM-ASE
$941
3/12Sun
2 stopsMultiple Airlines
46h 28mASE-GCM
3/16Thu
1 stopMultiple Airlines
28h 14mGCM-ASE
$994
2/25Sat
2 stopsUnited Airlines
20h 00mASE-SJU
3/4Sat
2 stopsUnited Airlines
23h 22mSJU-ASE
$1,215
2/25Sat
2 stopsUnited Airlines
20h 50mASE-SJU
3/3Fri
2 stopsUnited Airlines
22h 59mSJU-ASE
$1,234
2/25Sat
2 stopsUnited Airlines
20h 00mASE-SJU
3/4Sat
1 stopUnited Airlines
21h 02mSJU-ASE
$1,308
2/25Sat
1 stopMultiple Airlines
6h 58mASE-GCM
3/3Fri
2 stopsMultiple Airlines
47h 47mGCM-ASE
$1,405
3/12Sun
1 stopUnited Airlines
29h 06mASE-GCM
3/16Thu
1 stopUnited Airlines
28h 14mGCM-ASE
$1,493
2/25Sat
1 stopUnited Airlines
8h 38mASE-SJU
3/3Fri
2 stopsUnited Airlines
15h 17mSJU-ASE
$1,602
2/25Sat
1 stopAmerican Airlines
29h 28mASE-SJU
3/4Sat
1 stopAmerican Airlines
22h 55mSJU-ASE
$1,606
2/25Sat
1 stopUnited Airlines
6h 58mASE-GCM
3/3Fri
1 stopUnited Airlines
28h 14mGCM-ASE
$1,878

Search by stops

Search by airline

Search by price

Aspen - Caribbean Islands Flights

Departure:

Aspen (ASE)United States

Cabin classes:

$432
$837
$669
$141

Browse origins:

$529