$298 Find Cheap Flights from Aspen to Caribbean Islands

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 Islands departing on 2/23. 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

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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Aspen to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Aspen to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Book Cheap Aspen 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 Aspen 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 Aspen to Caribbean Islands

Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
3:50 pm - 10:00 am
ASE
-
SJU
15h 10m
2 stops
American Airlines Logo
1:30 am - 12:08 pm
SJU
-
ASE
13h 38m
2 stops
$501American Airlines
Sat, Feb 28 - Sat, Mar 7
American Airlines Logo
3:50 pm - 10:00 am
ASE
-
SJU
15h 10m
2 stops
American Airlines Logo
1:30 am - 3:06 pm
SJU
-
ASE
16h 36m
1 stop
$559American Airlines
Fri, Feb 27 - Sat, Mar 7
American Airlines Logo
12:39 pm - 11:31 pm
ASE
-
SJU
7h 52m
1 stop
American Airlines Logo
1:30 am - 12:08 pm
SJU
-
ASE
13h 38m
2 stops
$630American Airlines
Fri, Feb 27 - Sun, Mar 8
American Airlines Logo
12:39 pm - 5:24 am
ASE
-
SJU
13h 45m
1 stop
American Airlines Logo
6:33 am - 4:06 pm
SJU
-
ASE
11h 33m
1 stop
$688American Airlines
Wed, Mar 4 - Sat, Mar 14
American Airlines Logo
7:00 am - 11:31 pm
ASE
-
SJU
13h 31m
1 stop
American Airlines Logo
3:00 pm - 9:29 am
SJU
-
ASE
20h 29m
1 stop
$739American Airlines
Wed, Mar 4 - Sat, Mar 14
United Airlines Logo
10:05 am - 12:36 am
ASE
-
SJU
11h 31m
2 stops
United Airlines Logo
4:50 pm - 11:20 am
SJU
-
ASE
20h 30m
2 stops
$886United Airlines
Booking Insights

KAYAK's insights & trends for Aspen to Caribbean Islands flights

Get data-powered insights and trends into flights from Aspen 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 Aspen 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 $552, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$259
Flight from Aspen to George Town

FAQs - booking Caribbean Islands flights

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

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

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

 
See real verified KAYAK customer reviews for airlines flying from Aspen 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 Aspen 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.
7.2
American AirlinesOverall score based on 11211 reviews
7.2Comfort
6.9Entertainment
7.5Boarding
6.4Food
8.0Crew
Airline reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

2.0 MediocreManikandan, Jan 2026
DFW - ORD
Read more American Airlines reviews

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

Flight was canceled. I asked to be rerouted to OKC and then took an Uber.

AA did not allow to board a flight because my connecting flight from DFW had been canceled. I got on another flight to another city. No service on the plane and I did not use their entertainment system.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports