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Caribbean Islands

$288+ Cheap flights from Aspen (ASE) to Caribbean Islands

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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — SJU
Dec 18 — Dec 251
Thu 12/18
Thu 12/25
1 adult, Economy
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Cheap flight deals from Aspen to Caribbean Islands

Keep the following information in mind while searching for Aspen to Caribbean Islands flight deals. Data was last updated November 18, 2025.

Round-trip from

$365
(American Airlines)

One-way from

$288
(American Airlines)
From Aspen Pitkin County to Caribbean Islands
Search Deals
One-way flight from Aspen Pitkin County to Caribbean Islands
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Find flight deals from Aspen to Caribbean Islands

Cheapest flights from Aspen to Caribbean Islands
Explore the most affordable flight options available from Aspen to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 18, 2025.

This United Airlines deal was found by Cheapflights users on 11/17. 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 12/39:00 amASE - SJU
2 stops12h 36mUnited Airlines
Wed 12/102:25 pmSJU - ASE
1 stop8h 53mUnited Airlines
Deal found 11/17$612
This American Airlines deal was found by Cheapflights users on 11/17. 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.
Tue 11/2512:25 pmASE - SJU
1 stop14h 45mAmerican Airlines
Mon 12/16:42 pmSJU - ASE
2 stops20h 00mAmerican Airlines
Deal found 11/17$742
This American Airlines deal was found by Cheapflights users on 11/17. 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 12/37:33 amASE - SJU
1 stop10h 52mAmerican Airlines
Wed 12/107:00 amSJU - ASE
1 stop15h 34mAmerican Airlines
Deal found 11/17$745
This United Airlines deal was found by Cheapflights users on 11/18. 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 11/257:10 amASE - SJU
2 stops12h 12mUnited Airlines
Mon 12/12:25 pmSJU - ASE
1 stop8h 43mUnited Airlines
Deal found 11/18$812
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Sun 11/237:34 amASE - GCM
2 stops10h 54mAmerican Airlines
Fri 11/283:10 pmGCM - ASE
2 stops22h 32mAmerican Airlines
Deal found 11/18$1,071
This United Airlines deal was found by Cheapflights users on 11/17. 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 12/2312:57 pmASE - SJU
1 stop26h 28mUnited Airlines
Sat 1/37:45 amSJU - ASE
1 stop9h 42mUnited Airlines
Deal found 11/17$1,751

Cheapflights Fare Finder

 
Customize your flight search to find flights from Aspen to Caribbean Islands 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 November 18, 2025.
Use the filters below to find and compare flights from Aspen to Caribbean Islands that are best for you.

Fly from

Aspen

Fly to

Caribbean Islands

Route

Depart

Return

Price

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Thu 2/5

4:58 pm-10:48 am

2 stops14h 50m

San Juan Luis Munoz Marin Intl

Mon 2/9

7:12 pm-10:22 am

2 stops18h 10m

$365

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Thu 2/5

7:45 am-9:00 pm

1 stop10h 15m

San Juan Luis Munoz Marin Intl

Mon 2/9

7:45 am-2:17 pm

1 stop9h 32m

$594

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 12/3

9:00 am-12:36 am

2 stops12h 36m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:25 pm-8:18 pm

1 stop8h 53m

$612

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 12/3

7:33 am-9:25 pm

1 stop10h 52m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-7:34 pm

1 stop15h 34m

$745

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Sun 2/8

7:44 pm-11:50 am

2 stops14h 06m

George Town Owen Roberts Intl

Wed 2/11

3:45 pm-11:45 am

2 stops22h 00m

$750

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Sat 3/14

8:12 am-3:55 am

1 stop17h 43m

San Juan Luis Munoz Marin Intl

Sun 3/22

3:15 pm-9:51 am

1 stop20h 36m

$1,127

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Sat 3/14

5:16 pm-12:17 pm

2 stops17h 01m

San Juan Luis Munoz Marin Intl

Sun 3/22

3:52 pm-12:40 pm

2 stops22h 48m

$1,143

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Sun 2/8

1:33 pm-12:40 pm

1 stop21h 07m

George Town Owen Roberts Intl

Wed 2/11

2:05 pm-2:16 pm

1 stop26h 11m

$3,591

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Mon 2/23

6:57 pm-12:04 pm

2 stops15h 07m

$288

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Sun 2/22

7:22 pm-8:15 pm

2 stops22h 53m

$565

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Showing 1-10 of 12 results
1
2

Best time to book a flight from Aspen to Caribbean Islands

Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands 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 Islands
No data available for this route at this time. Please check back soon.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated November 18, 2025.
See what other customers who have flown with American Airlines from Aspen to Caribbean Islands have to say. 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
11,045 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.
American Airlines
7.2
Good
11,045 reviews
American Airlines
7.2
Good
11,045 reviews

Boarding

7.5

Entertainment

6.9

Overall

7.2

Comfort

7.2

Crew

8.0

Food

6.4

Reviews

1 / 20
4.0
Okay

Cameron,Nov 2025

PDX - LHR

The plane was very old...had no WiFi available. The crew were not friendly nor helpful.

Related info for your journey

Find useful and relevant information for your journey from Aspen to Caribbean Islands. 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 Islands?

    Aspen Pitkin County (ASE) is the airport you will fly out of if you book a flight from Aspen to Caribbean Islands. 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 Islands?

    There are many flights that can get you from Aspen to Caribbean Islands in 10h 15m. Fly via American Airlines or United Airlines to get the fastest option. The distance between Aspen and Caribbean Islands is about 2824 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Aspen to Caribbean Islands 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 Islands

Discover the top airline that operate flights from Aspen to Caribbean Islands. 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 November 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$336Average$588FlexibilityNo cancel feeOn-time69%

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