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Caribbean Islands

$365+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — SJU
feb. 25 — mar. 41
mié. 2/25
mié. 3/4
1 adult, Economy
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Cheap 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 enero 26, 2026.

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.
vie. 5/1511:59 pm
ANC
-
NAS
1 stop10h 58m
United Airlines
mié. 5/203:59 pm
NAS
-
ANC
2 stops23h 21m
United Airlines
Deal found 1/25$664
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.
dom. 3/299:04 pm
ANC
-
NAS
2 stops34h 59m
United Airlines
mié. 4/12:53 pm
NAS
-
ANC
2 stops35h 52m
United Airlines
Deal found 1/25$750
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 3/19:15 pm
ANC
-
SJU
1 stop13h 03m
Delta
mar. 3/107:00 am
SJU
-
ANC
2 stops21h 28m
Delta
Deal found 1/25$765
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/292:20 pm
ANC
-
SJU
2 stops17h 16m
Delta
vie. 11/67:30 am
SJU
-
ANC
2 stops20h 06m
Delta
Deal found 1/25$785
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/1611:23 pm
ANC
-
PUJ
1 stop30h 52m
Multiple Airlines
mié. 5/201:01 pm
PUJ
-
ANC
2 stops16h 58m
Multiple Airlines
Deal found 1/24$793
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.
lun. 5/49:00 pm
ANC
-
SJU
2 stops20h 24m
United Airlines
mié. 5/64:55 pm
SJU
-
ANC
2 stops28h 06m
United Airlines
Deal found 1/25$794
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/302:20 pm
ANC
-
SJU
2 stops17h 16m
Delta
sáb. 11/77:30 am
SJU
-
ANC
1 stop17h 04m
Delta
Deal found 1/25$805
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/309:08 pm
ANC
-
PUJ
1 stop16h 04m
Multiple Airlines
sáb. 11/79:38 am
PUJ
-
ANC
2 stops21h 33m
Multiple Airlines
Deal found 1/25$825
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.
mar. 5/198:30 pm
ANC
-
SJU
1 stop14h 12m
American Airlines
mié. 5/275:37 am
SJU
-
ANC
1 stop21h 00m
American Airlines
Deal found 1/26$845
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/189:15 pm
ANC
-
SJU
2 stops19h 09m
Delta
dom. 5/36:15 am
SJU
-
ANC
2 stops18h 22m
Delta
Deal found 1/26$850
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.
mié. 10/2811:45 pm
ANC
-
SJU
1 stop13h 40m
United Airlines
vie. 11/62:25 pm
SJU
-
ANC
1 stop13h 14m
United Airlines
Deal found 1/25$855
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.
vie. 10/308:55 pm
ANC
-
SJU
1 stop19h 05m
United Airlines
vie. 11/62:25 pm
SJU
-
ANC
1 stop13h 14m
United Airlines
Deal found 1/25$859

Find 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 enero 26, 2026.

Round-trip from

$664
(United Airlines)

One-way from

$253
(United Airlines)

Popular in

May

Cheapest in

August
From Anchorage to Caribbean Islands
Search Deals
One-way flight from Anchorage to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($54 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($17 potential savings vs. average RT price).
Search Deals

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 enero 26, 2026.
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

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

vie. 5/15

11:59 pm-2:57 pm

1 stop10h 58m

Nassau Intl

mié. 5/20

3:59 pm-11:20 am

2 stops23h 21m

$664

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

dom. 3/29

9:04 pm-12:03 pm

2 stops34h 59m

Nassau Intl

mié. 4/1

2:53 pm-10:45 pm

2 stops35h 52m

$750

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

dom. 3/1

9:15 pm-3:18 pm

1 stop13h 03m

San Juan Luis Munoz Marin Intl

mar. 3/10

7:00 am-12:28 am

2 stops21h 28m

$765

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

mar. 5/19

11:49 pm-5:38 pm

1 stop13h 49m

San Juan Luis Munoz Marin Intl

mié. 5/27

7:40 am-10:55 pm

2 stops19h 15m

$765

AnchoragePunta Cana

ANC - PUJ

ANCPUJ

Anchorage

sáb. 5/16

11:23 pm-10:15 am

1 stop30h 52m

Punta Cana

mié. 5/20

1:01 pm-1:59 am

2 stops16h 58m

$793

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

lun. 5/4

11:49 pm-9:24 pm

2 stops17h 35m

San Juan Luis Munoz Marin Intl

mié. 5/6

4:55 pm-5:01 pm

2 stops28h 06m

$794

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

lun. 5/18

1:25 am-11:01 pm

2 stops17h 36m

San Juan Luis Munoz Marin Intl

mié. 5/27

7:20 am-10:36 pm

2 stops19h 16m

$845

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

sáb. 4/18

9:15 pm-8:24 pm

2 stops19h 09m

San Juan Luis Munoz Marin Intl

dom. 5/3

6:15 am-8:37 pm

2 stops18h 22m

$850

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

lun. 3/2

11:45 pm-6:25 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

mié. 3/4

8:30 am-11:08 pm

2 stops19h 38m

$885

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

dom. 3/1

11:45 pm-6:25 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

jue. 3/5

2:25 pm-10:50 pm

1 stop13h 25m

$885

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 48 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, February is the cheapest month in which you can book a flight from Anchorage to Caribbean Islands (average of $380). Flying from Anchorage to Caribbean Islands in January is currently the most expensive (average of $1,021). 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.

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 enero 26, 2026.
Read through reviews of airlines operating flights from Anchorage to Caribbean Islands, such as 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.
Delta
7.9
Good
8,111 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,111 reviews
Delta
7.9
Good
8,111 reviews

Crew

8.5

Boarding

8.1

Food

7.2

Entertainment

7.8

Overall

7.9

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

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 10h 58m. United Airlines provides one of the quickest options available for as low as $664. The distance from Anchorage to Caribbean Islands is about 4133 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 American Airlines. According to our data, you can fly for as low as $328. Users have also found prices from $426 and $451 on Delta and United 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 - Punta Cana or Anchorage - Santo Domingo Las Americas 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, February is the cheapest month in which you can book a flight from Anchorage to Caribbean Islands (average of $380). Flying from Anchorage to Caribbean Islands in January is currently the most expensive (average of $1,021). 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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Alternative routes for Anchorage to Caribbean Islands

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Top 2 airlines flying from Anchorage to Caribbean Islands

Discover the top 2 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 enero 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$956FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$448Average$994FlexibilityNo cancel feeOn-time69%

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