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Caribbean Islands

$281+ Cheap flights from Anchorage (ANC) 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 11/17. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — SJU
Nov 1 — Nov 81
Sat 11/1
Sat 11/8
1 adult, Economy
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Cheap flight deals from Anchorage to Caribbean Islands

Keep the following information in mind while searching for Anchorage to Caribbean Islands flight deals. Data was last updated October 2, 2025.

Round-trip from

$744
(United Airlines)

One-way from

$281
(Kiwi.com)

Popular in

December

Cheapest in

August

Average price

$806
From Anchorage to Caribbean Islands
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One-way flight from Anchorage to Caribbean Islands
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Highest demand for flights based on searches. 6% potential increase in price ($64 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($31 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Anchorage to Caribbean Islands

Cheapest flights from Anchorage to Caribbean Islands
Explore the most affordable flight options available from Anchorage 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 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.
Tue 12/211:59 pmANC - SJU
2 stops17h 23mUnited Airlines
Wed 12/107:45 amSJU - ANC
2 stops20h 11mUnited Airlines
Deal found 10/1$744
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:20 pmANC - SJU
2 stops17h 36mDelta
Wed 12/37:15 amSJU - ANC
2 stops20h 27mDelta
Deal found 10/1$764
This United Airlines deal was found by Cheapflights users on 10/2. 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 10/259:04 pmANC - SJU
1 stop18h 56mUnited Airlines
Sat 11/17:10 amSJU - ANC
1 stop16h 49mUnited Airlines
Deal found 10/2$778
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/202:20 pmANC - SJU
2 stops18h 50mDelta
Thu 11/277:00 amSJU - ANC
2 stops20h 49mDelta
Deal found 10/1$819
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/112:38 amANC - SJU
2 stops15h 10mAmerican Airlines
Wed 12/107:00 amSJU - ANC
2 stops19h 44mAmerican Airlines
Deal found 10/1$824
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/232:20 pmANC - SJU
2 stops18h 50mDelta
Thu 11/277:00 amSJU - ANC
2 stops20h 49mDelta
Deal found 10/1$839
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/235:20 pmANC - SJU
2 stops16h 01mDelta
Fri 10/311:06 pmSJU - ANC
2 stops16h 53mDelta
Deal found 10/1$854
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.
Tue 11/1812:30 amANC - SDQ
2 stops20h 06mDelta
Thu 12/46:35 amSDQ - ANC
2 stops17h 29mDelta
Deal found 9/29$870
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 12/19:07 pmANC - STI
2 stops21h 44mUnited Airlines
Tue 12/96:00 amSTI - ANC
2 stops21h 56mUnited Airlines
Deal found 9/30$870
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:20 pmANC - STI
2 stops17h 46mDelta
Wed 12/106:35 amSTI - ANC
2 stops24h 18mDelta
Deal found 9/30$880
This American Airlines deal was found by Cheapflights users on 10/2. 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 11/18:52 pmANC - SDQ
2 stops16h 32mAmerican Airlines
Sat 11/86:00 amSDQ - ANC
2 stops18h 15mAmerican Airlines
Deal found 10/2$881
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/282:20 pmANC - STI
2 stops17h 46mDelta
Mon 12/86:35 amSTI - ANC
2 stops24h 18mDelta
Deal found 9/30$890

Cheapflights Fare Finder

 
Customize your flight search to find flights from Anchorage 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 Anchorage to Caribbean Islands that are best for you.

Fly from

Anchorage

Fly to

Caribbean Islands

Route

Depart

Return

Price

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Tue 2/3

11:45 pm-6:25 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Wed 2/11

2:25 pm-11:15 pm

1 stop13h 50m

$744

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Tue 1/6

9:55 pm-3:20 pm

1 stop12h 25m

San Juan Luis Munoz Marin Intl

Thu 1/15

4:25 pm-12:59 am

1 stop13h 34m

$744

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Sat 10/25

9:04 pm-8:00 pm

1 stop18h 56m

San Juan Luis Munoz Marin Intl

Sat 11/1

7:10 am-7:59 pm

1 stop16h 49m

$778

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sun 3/8

8:55 pm-2:55 pm

1 stop14h 00m

Nassau Intl

Sun 3/15

3:35 pm-10:34 pm

2 stops34h 59m

$780

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Fri 11/21

2:20 pm-4:59 pm

2 stops21h 39m

San Juan Luis Munoz Marin Intl

Thu 11/27

7:00 am-10:49 pm

2 stops20h 49m

$819

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Mon 12/1

12:38 am-8:48 pm

2 stops15h 10m

San Juan Luis Munoz Marin Intl

Wed 12/10

7:00 am-11:44 pm

2 stops21h 44m

$824

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Tue 11/25

11:59 pm-6:25 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Wed 12/3

4:52 pm-10:56 pm

2 stops35h 04m

$839

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Wed 11/26

11:59 pm-6:25 pm

1 stop13h 26m

San Juan Luis Munoz Marin Intl

Wed 12/3

4:52 pm-10:56 pm

2 stops35h 04m

$839

AnchorageSanto Domingo

ANC - SDQ

ANCSDQ

Anchorage

Tue 11/18

12:30 am-1:36 am

2 stops20h 06m

Santo Domingo Las Americas

Thu 12/4

6:35 am-7:04 pm

2 stops17h 29m

$870

AnchorageSantiago de los Caballeros

ANC - STI

ANCSTI

Anchorage

Tue 12/2

5:55 am-12:59 pm

2 stops26h 04m

Santiago de los Caballeros

Thu 12/11

8:57 pm-7:04 pm

2 stops27h 07m

$870

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/2

Showing 1-10 of 60 results
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Best time to book a flight from Anchorage to Caribbean Islands

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

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

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

What is the cheapest time of day to fly from ANC to EPX?

Find hourly flight availability from Anchorage to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Anchorage to Caribbean Islands as you normally would.

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.
Read through reviews of airlines operating flights from Anchorage to Caribbean Islands, such as Alaska Airlines and Delta. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very good
10,994 reviews

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Alaska Airlines
8.0
Very good
10,994 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.
Delta
8.0
Very good
7,962 reviews
Alaska Airlines
8.0
Very good
10,994 reviews

Overall

8.0

Food

7.1

Crew

8.5

Comfort

7.8

Boarding

8.1

Entertainment

7.0

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

BOS - HNL

The flight was awesome but a little long. I would prefer a flight with a layover. The amount of space available was minimal and a little uncomfortable for that long of a flight.

Related info for your journey

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

    Located just 4.4 mi from the city center, Anchorage (ANC) is the airport most travelers will use when flying to Caribbean Islands from Anchorage.

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

    A quick flight from Anchorage to Caribbean Islands can take about 12h 25m. United Airlines provides one of the quickest options available for as low as $744. The distance from Anchorage to Caribbean Islands is about 4905 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for United Airlines. According to our data, you can fly for as low as $420. Users have also found prices from $431 and $566 on Delta and American Airlines, respectively.

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

    When deciding which route to take from Anchorage to Caribbean Islands consider Anchorage - San Juan Luis Munoz Marin Intl, Anchorage - Santo Domingo Las Americas or Anchorage - Punta Cana as they are the most popular.

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

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

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

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

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

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

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

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Top 4 airlines flying from Anchorage to Caribbean Islands

Discover the top 4 airlines that operate flights from Anchorage 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
DeltaCheapest$292Average$1,019FlexibilityNo cancel feeOn-timeN/A
Alaska AirlinesCheapest$559Average$649FlexibilityNo cancel feeOn-time75%
United AirlinesCheapest$593Average$994FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$782Average$972FlexibilityNo cancel feeOn-time71%

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