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$191+ Cheap flights from Aspen (ASE) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — SJU
Mar 15 — Mar 221
Sun 3/15
Sun 3/22
1 adult, Economy
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Cheap flight deals from Aspen to Caribbean

Cheapest flights from Aspen to Caribbean
Explore the most affordable flight options available from Aspen to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 13, 2026.

This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/189:05 am
ASE
-
SJU
1 stop8h 55m
United Airlines
Wed 2/257:40 am
SJU
-
ASE
2 stops12h 07m
United Airlines
Deal found 2/10$518
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/43:46 pm
ASE
-
SJU
1 stop10h 38m
American Airlines
Sat 3/143:00 pm
SJU
-
ASE
1 stop20h 29m
American Airlines
Deal found 2/13$575
This United Airlines deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:00 pm
ASE
-
GCM
2 stops21h 30m
United Airlines
Thu 10/294:45 pm
GCM
-
ASE
2 stops19h 06m
United Airlines
Deal found 2/9$636
This American Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/51:24 pm
ASE
-
SJU
1 stop13h 00m
American Airlines
Sun 3/86:33 am
SJU
-
ASE
1 stop16h 21m
American Airlines
Deal found 2/10$640
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/267:55 am
ASE
-
SJU
2 stops11h 27m
United Airlines
Mon 3/27:40 am
SJU
-
ASE
1 stop10h 02m
United Airlines
Deal found 2/11$672
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/47:55 am
ASE
-
SJU
2 stops11h 27m
United Airlines
Sat 3/141:25 pm
SJU
-
ASE
1 stop30h 15m
United Airlines
Deal found 2/11$685

Find flight deals from Aspen to Caribbean

Keep the following information in mind while searching for Aspen to Caribbean flight deals. Data was last updated February 13, 2026.

Round-trip from

$575
(American Airlines)

One-way from

$191
(American Airlines)
From Aspen Pitkin County to Caribbean
Search Deals
One-way flight from Aspen Pitkin County to Caribbean
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aspen to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
Use the filters below to find and compare flights from Aspen to Caribbean that are best for you.

Fly from

Aspen

Fly to

Caribbean

Route

Depart

Return

Price

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 3/4

3:46 pm-5:24 am

1 stop10h 38m

San Juan Luis Munoz Marin Intl

Sat 3/14

3:00 pm-9:29 am

1 stop20h 29m

$575

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Thu 3/5

1:24 pm-5:24 am

1 stop13h 00m

San Juan Luis Munoz Marin Intl

Sun 3/8

6:33 am-8:54 pm

1 stop16h 21m

$640

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Tue 3/24

2:47 pm-5:28 am

1 stop12h 41m

$191

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Mon 3/23

7:24 pm-9:00 am

2 stops11h 36m

$191

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 2/18

9:05 am-9:00 pm

1 stop8h 55m

$271

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 2/18

2:47 pm-10:00 am

2 stops16h 13m

$271

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Mon 2/23

6:28 pm-1:15 pm

2 stops16h 47m

$332

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Mon 2/23

7:24 pm-2:45 pm

2 stops17h 21m

$376

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Tue 3/24

12:19 pm-5:05 pm

3 stops26h 46m

$895

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Mon 2/23

7:24 pm-10:25 am

3 stops37h 01m

$1,234

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 11 results
1
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Best time to book a flight from Aspen to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Aspen with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Aspen to Caribbean
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 13, 2026.
Peruse reviews from past customers who have flown with American Airlines from Aspen to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,275 reviews

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.
American Airlines
7.2
Good
11,275 reviews
American Airlines
7.2
Good
11,275 reviews

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Boarding

7.5

Reviews

1 / 20
2.0
Mediocre

Susie,Jan 2026

CLT - TPA

This flight was delayed 3 or 4 times. We had boarded the plane, sat on plane for a good 30 minutes, then we had to board the aircraft, walk to a different gate, wait and then board another aircraft. We arrived in Tampa 4 hours later than the original booking. I feel there should have been some sort of compensation especially for the advantage members.

Related info for your journey

Find useful and relevant information for your journey from Aspen to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Aspen to Caribbean?

    Aspen Pitkin County (ASE) is the airport you will fly out of if you book a flight from Aspen to Caribbean. It is only a 3.5 mi journey to Pitkin County (ASE) from Aspen’s city center.

  • How long is the flight from Aspen to Caribbean?

    For as low as $575, American Airlines can have you in Caribbean from Aspen in 10h 38m. The distance between Aspen and Caribbean is about 2824 mi.

  • Can I find deals for flights from Aspen to Caribbean that include hotel bookings?

    Yes. In addition to deals on Aspen to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aspen to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aspen to Caribbean.

  • Can I find deals for business class flights from Aspen to Caribbean?

    Yes. Cheapflights offers flight deals from Aspen to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

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Top airline flying from Aspen to Caribbean

Discover the top airline that operate flights from Aspen to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 13, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$345Average$690FlexibilityNo cancel feeOn-time71%

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