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$289+ Cheap flights from Vail (EGE) 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 1/1. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — SJU
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Vail to Caribbean

Keep the following information in mind while searching for Vail to Caribbean flight deals. Data was last updated September 11, 2025.

Round-trip from

$442
(American Airlines)

One-way from

$289
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$334
From Vail Eagle County to Caribbean
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One-way flight from Vail Eagle County to Caribbean
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Highest demand for flights based on searches. 19% potential increase in price ($108 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($22 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Vail to Caribbean

Cheapest flights from Vail to Caribbean
Explore the most affordable flight options available from Vail to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/248:08 amEGE - SJU
2 stops24h 58mAmerican Airlines
Wed 10/297:05 amSJU - EGE
2 stops13h 52mAmerican Airlines
Deal found 9/9$442
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 10/241:40 pmEGE - SJU
2 stops24h 02mUnited Airlines
Wed 10/291:25 pmSJU - EGE
1 stop9h 06mUnited Airlines
Deal found 9/11$666
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 9/267:05 amEGE - SJU
2 stops14h 52mUnited Airlines
Tue 9/302:00 pmSJU - EGE
1 stop8h 08mUnited Airlines
Deal found 9/11$745
This American Airlines deal was found by Cheapflights users on 9/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/67:44 amEGE - STT
2 stops28h 41mAmerican Airlines
Wed 12/106:17 pmSTT - EGE
2 stops27h 55mAmerican Airlines
Deal found 9/9$809
This United Airlines deal was found by Cheapflights users on 9/8. 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 12/61:30 pmEGE - STT
1 stop22h 00mUnited Airlines
Wed 12/102:15 pmSTT - EGE
2 stops25h 09mUnited Airlines
Deal found 9/8$1,075

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vail 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 September 11, 2025.
Use the filters below to find and compare flights from Vail to Caribbean that are best for you.

Fly from

Vail

Fly to

Caribbean

Route

Depart

Return

Price

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Fri 10/24

8:08 am-11:06 am

2 stops24h 58m

San Juan Luis Munoz Marin Intl

Wed 10/29

7:05 am-6:57 pm

2 stops13h 52m

$442

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Tue 3/3

2:39 pm-4:55 am

1 stop11h 16m

San Juan Luis Munoz Marin Intl

Wed 3/4

4:25 pm-12:47 pm

2 stops23h 22m

$509

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Tue 3/3

7:15 am-6:25 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Wed 3/4

2:25 pm-8:05 pm

1 stop8h 40m

$600

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Fri 10/24

1:40 pm-3:42 pm

2 stops24h 02m

San Juan Luis Munoz Marin Intl

Wed 10/29

1:25 pm-8:31 pm

1 stop9h 06m

$666

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Sat 12/6

7:44 am-3:25 pm

2 stops28h 41m

Saint Thomas Island Cyril E King

Wed 12/10

6:17 pm-7:12 pm

2 stops27h 55m

$809

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Sat 12/6

1:30 pm-2:30 pm

1 stop22h 00m

Saint Thomas Island Cyril E King

Wed 12/10

2:15 pm-12:24 pm

2 stops25h 09m

$1,075

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Thu 1/1

10:34 am-5:04 am

1 stop15h 30m

$289

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 1/10

2:32 pm-1:35 pm

2 stops20h 03m

$334

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 1/10

12:35 pm-9:00 pm

1 stop29h 25m

$397

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 1/10

11:35 am-11:58 pm

1 stop9h 23m

$445

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

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

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Vail 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 Vail to Caribbean

What is the cheapest month to book a flight from Vail to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Vail to Caribbean (average of $254). Flying from Vail to Caribbean 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.

Related info for your journey

Find useful and relevant information for your journey from Vail 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 Vail to Caribbean?

    Vail Eagle County (EGE), located 28.9 mi from the city center, is the airport you fly out of when you book flights from Vail to Caribbean.

  • How long is the flight from Vail to Caribbean?

    There are many flights that can get you from Vail to Caribbean in 22h. Fly via American Airlines or United Airlines to get the fastest option. There are 2893 mi between Vail and Caribbean. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Vail to Caribbean one-way?

    One-way options have recently been found by users for as low as $289 on American Airlines. Other airlines that offer cheap prices include United Airlines from $397 and Delta from $445 one-way.

  • What are the most popular routes from Vail to Caribbean?

    Most travelers choose Vail Eagle County - San Juan Luis Munoz Marin Intl, Vail Eagle County - Saint Thomas Island Cyril E King or Vail Eagle County - Puerto Plata La Union when deciding on the best route from Vail to Caribbean.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vail 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.

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

    Currently, September is the cheapest month in which you can book a flight from Vail to Caribbean (average of $254). Flying from Vail to Caribbean 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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