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$294+ 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 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
EGE — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap 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 January 29, 2026.

This American Airlines deal was found by Cheapflights users on 1/28. 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 3/74:12 pm
SJU
-
EGE
1 stop19h 54m
American Airlines
Deal found 1/28$514
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/283:11 pm
EGE
-
SJU
1 stop27h 15m
United Airlines
Sat 3/73:25 pm
SJU
-
EGE
1 stop9h 22m
United Airlines
Deal found 1/28$652
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
Fri 3/137:05 am
SJU
-
EGE
2 stops15h 19m
United Airlines
Deal found 1/27$654
This United Airlines deal was found by Cheapflights users on 1/28. 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 1/28$709
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 1/26. 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 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 2/263:05 pm
STT
-
EGE
1 stop9h 42m
United Airlines
Deal found 1/26$754
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.
Thu 3/510:48 am
EGE
-
SJU
1 stop15h 36m
American Airlines
Fri 3/131:30 am
SJU
-
EGE
1 stop19h 52m
American Airlines
Deal found 1/27$789
This United Airlines deal was found by Cheapflights users on 1/28. 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 2/153:11 pm
EGE
-
STT
2 stops19h 45m
United Airlines
Wed 2/181:02 pm
STT
-
EGE
2 stops24h 35m
United Airlines
Deal found 1/28$965
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.
Fri 5/87:05 am
EGE
-
STT
2 stops31h 55m
United Airlines
Fri 5/224:45 pm
STT
-
EGE
3 stops29h 20m
United Airlines
Deal found 1/27$3,717

Find flight deals from Vail to Caribbean

Keep the following information in mind while searching for Vail to Caribbean flight deals. Data was last updated January 29, 2026.

Round-trip from

$514
(American Airlines)

One-way from

$294
(American Airlines)

Popular in

December

Cheapest in

August

Average price

$377
From Vail Eagle County to Caribbean
Search Deals
One-way flight from Vail Eagle County to Caribbean
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
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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 January 29, 2026.
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

Sat 2/28

4:17 pm-10:00 am

2 stops14h 43m

San Juan Luis Munoz Marin Intl

Sat 3/7

4:12 pm-9:06 am

1 stop19h 54m

$514

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sat 2/28

3:11 pm-9:26 pm

1 stop27h 15m

San Juan Luis Munoz Marin Intl

Sat 3/7

3:25 pm-9:47 pm

1 stop9h 22m

$652

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

Fri 3/13

7:05 am-8:24 pm

2 stops15h 19m

$654

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

6:33 am-7:22 pm

1 stop14h 49m

$709

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

$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

12:32 pm-1:56 pm

2 stops22h 24m

Saint Thomas Island Cyril E King

Thu 2/26

3:05 pm-9:47 pm

1 stop9h 42m

$754

VailSaint Thomas Island

EGE - STT

EGESTT

Vail Eagle County

Sun 2/15

3:11 pm-1:56 pm

2 stops19h 45m

Saint Thomas Island Cyril E King

Wed 2/18

1:02 pm-10:37 am

2 stops24h 35m

$965

VailSan Juan

EGE - SJU

EGESJU

Vail Eagle County

Sun 4/5

10:48 am-4:24 am

1 stop15h 36m

$294

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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, April is the cheapest month in which you can book a flight from Vail to Caribbean (average of $130). Flying from Vail to Caribbean 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. 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 14h 43m. Fly via American Airlines or United Airlines to get the fastest option. There are 2836 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 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, April is the cheapest month in which you can book a flight from Vail to Caribbean (average of $130). Flying from Vail to Caribbean 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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