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Caribbean Islands

$294+ Cheap flights from Vail (EGE) 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — SJU
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Vail to Caribbean Islands

Cheapest flights from Vail to Caribbean Islands
Explore the most affordable flight options available from Vail to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This American Airlines deal was found by Cheapflights users on 1/25. 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 2/1512:05 pm
EGE
-
SJU
1 stop14h 19m
American Airlines
Wed 2/255:42 pm
SJU
-
EGE
1 stop20h 20m
American Airlines
Deal found 1/25$372
This United Airlines deal was found by Cheapflights users on 1/25. 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.
Sun 2/158:00 am
EGE
-
SJU
2 stops11h 22m
United Airlines
Tue 2/242:05 am
SJU
-
EGE
2 stops15h 10m
United Airlines
Deal found 1/25$397
This American Airlines deal was found by Cheapflights users on 1/26. 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 2/284:17 pm
EGE
-
SJU
2 stops14h 43m
American Airlines
Sat 3/77:33 am
SJU
-
EGE
1 stop14h 55m
American Airlines
Deal found 1/26$480
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/283:30 pm
EGE
-
SJU
2 stops11h 41m
United Airlines
Sat 3/73:25 pm
SJU
-
EGE
1 stop9h 22m
United Airlines
Deal found 1/25$495
This American Airlines deal was found by Cheapflights users on 1/25. 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 3/1812:05 pm
EGE
-
SJU
1 stop14h 19m
American Airlines
Sat 3/211:30 am
SJU
-
EGE
1 stop19h 52m
American Airlines
Deal found 1/25$709
This United Airlines deal was found by Cheapflights users on 1/24. 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 1/268:30 am
EGE
-
SJU
1 stop9h 30m
United Airlines
Wed 1/282:25 pm
SJU
-
EGE
1 stop9h 24m
United Airlines
Deal found 1/24$715
This American Airlines deal was found by Cheapflights users on 1/27. 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 5/88:00 am
EGE
-
STT
2 stops27h 05m
American Airlines
Fri 5/224:48 pm
STT
-
EGE
2 stops28h 04m
American Airlines
Deal found 1/27$720
This American Airlines deal was found by Cheapflights users on 1/27. 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 3/411:14 am
EGE
-
SJU
1 stop9h 20m
American Airlines
Fri 3/131:30 am
SJU
-
EGE
1 stop19h 52m
American Airlines
Deal found 1/27$724
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/2412:32 pm
EGE
-
STT
2 stops22h 24m
United Airlines
Thu 2/261:02 pm
STT
-
EGE
2 stops24h 52m
United Airlines
Deal found 1/25$733
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/48:00 am
EGE
-
SJU
2 stops11h 22m
United Airlines
Sat 3/147:05 am
SJU
-
EGE
2 stops15h 19m
United Airlines
Deal found 1/27$747
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/1011:53 am
EGE
-
STT
1 stop26h 12m
American Airlines
Sat 2/146:25 pm
STT
-
EGE
2 stops20h 20m
American Airlines
Deal found 1/25$895
This United Airlines deal was found by Cheapflights users on 1/25. 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 2/108:30 am
EGE
-
STT
3 stops26h 26m
United Airlines
Sat 2/145:25 pm
STT
-
EGE
3 stops21h 53m
United Airlines
Deal found 1/25$978

Find flight deals from Vail to Caribbean Islands

Keep the following information in mind while searching for Vail to Caribbean Islands flight deals. Data was last updated January 27, 2026.

Round-trip from

$372
(American Airlines)

One-way from

$294
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$377
From Vail Eagle County to Caribbean Islands
Search Deals
One-way flight from Vail Eagle County to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($49 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Vail 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 January 27, 2026.
Use the filters below to find and compare flights from Vail to Caribbean Islands that are best for you.

Fly from

Vail

Fly to

Caribbean Islands

Route

Depart

Return

Price

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sun 2/15

12:05 pm-5:24 am

1 stop14h 19m

San Juan Luis Munoz Marin Intl

Wed 2/25

5:42 pm-11:02 am

1 stop20h 20m

$372

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sun 2/15

8:00 am-10:22 pm

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Tue 2/24

2:05 am-2:15 pm

2 stops15h 10m

$397

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 2/28

4:17 pm-10:00 am

2 stops14h 43m

San Juan Luis Munoz Marin Intl

Sat 3/7

7:33 am-7:28 pm

1 stop14h 55m

$480

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 2/28

3:30 pm-6:11 am

2 stops11h 41m

San Juan Luis Munoz Marin Intl

Sat 3/7

3:25 pm-9:47 pm

1 stop9h 22m

$495

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Wed 3/18

12:05 pm-4:24 am

1 stop14h 19m

San Juan Luis Munoz Marin Intl

Sat 3/21

1:30 am-7:22 pm

1 stop19h 52m

$709

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Fri 5/8

8:00 am-1:05 pm

2 stops27h 05m

Saint Thomas Island Cyril E King

Fri 5/22

4:48 pm-6:52 pm

2 stops28h 04m

$720

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Wed 3/4

11:14 am-11:34 pm

1 stop9h 20m

San Juan Luis Munoz Marin Intl

Fri 3/13

1:30 am-7:22 pm

1 stop19h 52m

$724

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Tue 2/24

1:35 pm-1:56 pm

2 stops21h 21m

Saint Thomas Island Cyril E King

Thu 2/26

1:02 pm-10:54 am

2 stops24h 52m

$733

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Wed 3/4

8:00 am-10:22 pm

2 stops11h 22m

San Juan Luis Munoz Marin Intl

Sat 3/14

7:05 am-8:24 pm

2 stops15h 19m

$747

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Tue 2/10

2:52 pm-5:05 pm

2 stops23h 13m

Saint Thomas Island Cyril E King

Sat 2/14

4:37 pm-9:54 am

2 stops20h 17m

$948

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 13 results
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Best time to book a flight from Vail to Caribbean Islands

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

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

Currently, April is the cheapest month in which you can book a flight from Vail to Caribbean Islands (average of $130). Flying from Vail to Caribbean Islands in December is currently the most expensive (average of $293). 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 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 Vail to Caribbean Islands?

    If you book a flight to Caribbean Islands from Vail, you will be flying from Eagle County, which is the city’s only airport. Vail Eagle County (EGE) is located 28.9 mi from the center of Vail.

  • How long is the flight from Vail to Caribbean Islands?

    A quick flight from Vail to Caribbean Islands can take about 11h 22m. American Airlines provides one of the quickest options available for as low as $397. Vail and Caribbean Islands are separated by a distance of 2836 mi. Both multi-stop and nonstop flights can be found to your destination and back.

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

    When deciding which route to take from Vail to Caribbean Islands consider Vail Eagle County - San Juan Luis Munoz Marin Intl, Vail Eagle County - Puerto Plata La Union or Vail Eagle County - Saint Thomas Island Cyril E King as they are the most popular.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Vail 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 Vail to Caribbean Islands?

    Currently, April is the cheapest month in which you can book a flight from Vail to Caribbean Islands (average of $130). Flying from Vail to Caribbean Islands in December is currently the most expensive (average of $293). 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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