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Caribbean Islands

$183+ 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 1/29. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — SJU
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
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 October 2, 2025.

Round-trip from

$604
(United Airlines)

One-way from

$183
(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 October 2, 2025.

This United Airlines deal was found by Cheapflights users on 9/30. 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.
Mon 12/86:30 pmASE - GCM
2 stops20h 00mUnited Airlines
Mon 12/155:45 pmGCM - ASE
2 stops17h 16mUnited Airlines
Deal found 9/30$604
This American Airlines deal was found by Cheapflights users on 9/29. 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.
Sat 12/67:33 amASE - SJU
2 stops23h 34mAmerican Airlines
Wed 12/106:00 amSJU - ASE
2 stops16h 34mAmerican Airlines
Deal found 9/29$609
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 12/63:35 pmASE - GCM
2 stops19h 40mUnited Airlines
Wed 12/105:45 pmGCM - ASE
2 stops41h 16mUnited Airlines
Deal found 10/1$622
This United Airlines deal was found by Cheapflights users on 10/1. 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.
Sat 12/69:00 amASE - SJU
2 stops12h 36mUnited Airlines
Wed 12/102:25 pmSJU - ASE
1 stop9h 53mUnited Airlines
Deal found 10/1$622
This Delta deal was found by Cheapflights users on 9/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/61:15 pmASE - GCM
1 stop21h 20mDelta
Wed 12/101:50 pmGCM - ASE
1 stop23h 47mDelta
Deal found 9/29$3,013

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 October 2, 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

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Mon 12/8

6:30 pm-4:30 pm

2 stops20h 00m

George Town Owen Roberts Intl

Mon 12/15

5:45 pm-9:01 am

2 stops17h 16m

$604

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Sat 12/6

7:33 am-10:07 am

2 stops23h 34m

San Juan Luis Munoz Marin Intl

Wed 12/10

6:00 am-7:34 pm

2 stops16h 34m

$609

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Sat 12/6

5:12 pm-1:15 pm

2 stops18h 03m

George Town Owen Roberts Intl

Wed 12/10

5:45 pm-9:01 am

2 stops41h 16m

$622

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Sat 12/6

9:00 am-12:36 am

2 stops12h 36m

San Juan Luis Munoz Marin Intl

Wed 12/10

2:25 pm-9:18 pm

1 stop9h 53m

$622

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Mon 2/2

5:02 pm-3:40 pm

2 stops19h 38m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:25 pm-8:59 am

1 stop21h 34m

$780

AspenGeorge Town

ASE - GCM

ASEGCM

Aspen Pitkin County

Sat 12/6

1:15 pm-12:35 pm

1 stop21h 20m

George Town Owen Roberts Intl

Wed 12/10

1:50 pm-11:37 am

1 stop23h 47m

$3,013

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Fri 1/30

2:49 pm-10:48 am

2 stops16h 59m

$183

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Thu 1/29

2:49 pm-10:48 am

2 stops16h 59m

$183

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 1/7

8:53 am-12:36 am

2 stops12h 43m

$290

AspenSan Juan

ASE - SJU

ASESJU

Aspen Pitkin County

Wed 1/7

7:30 am-10:22 pm

1 stop11h 52m

$413

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 17 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 October 2, 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
11,033 reviews

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac
American Airlines
7.2
Good
11,033 reviews
American Airlines
7.2
Good
11,033 reviews

Overall

7.2

Boarding

7.5

Entertainment

6.9

Crew

8.0

Food

6.4

Comfort

7.2

Reviews

1 / 20
2.0
Mediocre

Jeremy,Sep 2025

SAN - PHL

Terrible. Bad customer service and unacceptable delay on the tarmac

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 20h. Fly via United Airlines or American Airlines to get the fastest option. The distance between Aspen and Caribbean Islands is about 2049 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.

  • What is the cheapest month to book a flight from Aspen to Caribbean Islands?

    Currently, September is the cheapest month in which you can book a flight from Aspen to Caribbean Islands (average of $254). Flying from Aspen to Caribbean Islands in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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 October 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$336Average$534FlexibilityNo cancel feeOn-time69%

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