$183 Find Cheap Flights from Aspen to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Aspen to Caribbean departing on 1/29. 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

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Flight Deals

Book Cheap Aspen to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Aspen to Caribbean 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 Aspen to Caribbean

Sat, Jan 31 - Tue, Feb 3
United Airlines Logo
5:02 pm - 6:11 amASE-SJU
10h 09m2 stops
United Airlines Logo
8:10 am - 6:39 pmSJU-ASE
13h 29m2 stops
$455United Airlines
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Mon, Feb 2 - Tue, Feb 3
American Airlines Logo
2:49 pm - 12:32 pmASE-SJU
18h 43m2 stops
American Airlines Logo
4:27 pm - 11:53 amSJU-ASE
22h 26m2 stops
$468American Airlines
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Sun, Feb 1 - Sat, Feb 7
American Airlines Logo
10:52 am - 11:59 pmASE-SJU
10h 07m2 stops
American Airlines Logo
5:51 pm - 11:53 amSJU-ASE
21h 02m2 stops
$473American Airlines
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Thu, Nov 6 - Thu, Nov 13
American Airlines Logo
7:34 am - 5:20 amASE-SJU
18h 46m1 stop
American Airlines Logo
6:00 am - 7:30 pmSJU-ASE
16h 30m2 stops
$506American Airlines
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Tue, Feb 3 - Wed, Feb 4
United Airlines Logo
8:53 am - 10:22 pmASE-SJU
10h 29m2 stops
United Airlines Logo
8:10 am - 4:52 pmSJU-ASE
11h 42m2 stops
$507United Airlines
Find Deal
Fri, Jan 30 - Tue, Feb 3
United Airlines Logo
10:35 am - 12:36 amASE-SJU
11h 01m2 stops
United Airlines Logo
8:10 am - 6:39 pmSJU-ASE
13h 29m2 stops
$512United Airlines
Find Deal
Mon, Feb 2 - Wed, Feb 4
United Airlines Logo
7:00 am - 6:25 pmASE-SJU
8h 25m1 stop
United Airlines Logo
8:10 am - 4:52 pmSJU-ASE
11h 42m2 stops
$534United Airlines
Find Deal
Sat, Jan 31 - Wed, Feb 4
United Airlines Logo
12:36 pm - 6:11 amASE-SJU
14h 35m2 stops
United Airlines Logo
7:45 am - 2:17 pmSJU-ASE
9h 32m1 stop
$565United Airlines
Find Deal
Fri, Jan 30 - Mon, Feb 2
United Airlines Logo
10:35 am - 12:36 amASE-SJU
11h 01m2 stops
United Airlines Logo
7:45 am - 2:17 pmSJU-ASE
9h 32m1 stop
$569United Airlines
Find Deal
Tue, Feb 3 - Tue, Feb 3
United Airlines Logo
8:53 am - 10:22 pmASE-SJU
10h 29m2 stops
United Airlines Logo
2:05 am - 12:47 pmSJU-ASE
13h 42m2 stops
$575United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Aspen to Caribbean flights

Get data-powered insights and trends into flights from Aspen to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Aspen to Caribbean?

The average price of all round-trip flights from Aspen to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Aspen to Caribbean, look for departures on Fridays and avoid leaving on a Tuesday, as it's usually the priciest day. When flying back from Caribbean, Monday is the cheapest day to fly and Friday is the most expensive.

Good to know

Cheapest flight$183
Flight from Aspen to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Aspen to Caribbean?

    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 Aspen to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Aspen to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Aspen to Caribbean 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 Aspen to Caribbean?

    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 Aspen to Caribbean 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 Aspen to Caribbean?

    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 Aspen to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the evening, when round-trip flights cost $540 on average. Morning departures are around 10% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the morning, which is peak travel time and where the average cost of a ticket is $588.

Reviews of the top airlines flying from Aspen to Caribbean

 
Need help choosing which airline to fly with from Aspen to Caribbean? 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.
7.4
United AirlinesOverall score based on 8968 reviews
7.3Comfort
6.6Food
7.7Boarding
7.1Entertainment
8.1Crew
Airline reviews

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

2.0 MediocreAnonymous, Sep 2025DEN - ORD
Read more United Airlines reviews

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Terrible. They wouldn't allow me on my flight on the 14th..

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

Impressed with the service despite turbulence because of the weather. Both flights arrived before their scheduled times.

Great experience…left a bit behind schedule but made up fir that in the air and landed 10 minutes early 😁

The seat and leg room was not good. The food and beverage service was good.

For economy, it was very good. Staff was great, they even let some of us change seats for more leg room... Put an empty seat between us which was fantastic for a 12hr flight. Onboard entertainment was excellent, I think over 200 choices of movies/tv/etc The bad was the barely/nonfunctional wifi that cost either $16.99 or 1700 miles (full flight). It was atrocious... Definitely the worst of the last 3 long haul major airlines I was on the last few months.

Electric plugs didn't work. Entertainment system wasn't working

The design of the light switch on the arm rest is ridiculous.

The gate attendant let me walk right by her with a bag too big for the overhead compartment

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Food should be better quality. Video screens have poor resolution and the library of movies is poor. The other airlines are much better.

the trip to madrid was uncomfortable with my legs touching the seat in front of me

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

We were delayed for a “couple of maintenance issues.” They were resolved rather quickly but a computer glitch caused someone in the airport to have to bring a physical copy of the paperwork so we could leave. I don’t know where they had to drive from to get to our plane but it took forever & we were 1 1/2 hrs late in leaving. The flight itself was fine.

You can plug your phone in & use their wifi to watch movies, etc, but the plane’s wifi was disconnected for most of the flight.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

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