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Caribbean

$319+ Cheap flights from Alaska 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 2/18. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — SJU
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Alaska to Caribbean

Cheapest flights from Alaska to Caribbean
Explore the most affordable flight options available from Alaska to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

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.
Thu 7/1611:59 pm
ANC
-
NAS
1 stop10h 58m
United Airlines
Sat 7/255:00 pm
NAS
-
ANC
2 stops22h 20m
United Airlines
Deal found 1/26$703
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 3/159:10 pm
ANC
-
NAS
1 stop14h 12m
United Airlines
Sun 3/221:05 pm
NAS
-
ANC
2 stops34h 56m
United Airlines
Deal found 1/28$737
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.
Sun 3/299:04 pm
ANC
-
NAS
2 stops34h 59m
United Airlines
Wed 4/12:53 pm
NAS
-
ANC
2 stops35h 52m
United Airlines
Deal found 1/26$750
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.
Mon 3/1611:52 pm
ANC
-
SJU
2 stops16h 08m
United Airlines
Wed 3/257:05 am
SJU
-
ANC
2 stops16h 56m
United Airlines
Deal found 1/28$765
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.
Mon 5/48:55 pm
FAI
-
SJU
2 stops20h 29m
United Airlines
Wed 5/64:55 pm
SJU
-
FAI
2 stops30h 47m
United Airlines
Deal found 1/28$785
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.
Sat 2/219:00 am
ANC
-
SJU
2 stops23h 17m
United Airlines
Fri 2/278:05 am
SJU
-
ANC
2 stops16h 41m
United Airlines
Deal found 1/27$790
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.
Mon 5/411:49 pm
ANC
-
SJU
2 stops17h 35m
United Airlines
Wed 5/64:55 pm
SJU
-
ANC
2 stops28h 06m
United Airlines
Deal found 1/28$794
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 3/159:10 pm
ANC
-
SJU
1 stop13h 30m
United Airlines
Tue 3/241:25 pm
SJU
-
ANC
1 stop13h 25m
United Airlines
Deal found 1/28$798
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:15 pm
ANC
-
SJU
1 stop13h 03m
Delta
Tue 3/106:15 am
SJU
-
ANC
2 stops16h 36m
Delta
Deal found 1/28$810
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 3/1811:52 pm
ANC
-
SJU
2 stops16h 08m
United Airlines
Tue 3/247:05 am
SJU
-
ANC
2 stops16h 56m
United Airlines
Deal found 1/27$816
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.
Mon 2/2311:45 pm
ANC
-
SJU
2 stops17h 37m
United Airlines
Fri 2/277:40 am
SJU
-
ANC
2 stops17h 06m
United Airlines
Deal found 1/27$839
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.
Tue 3/1712:29 am
ANC
-
SJU
2 stops16h 05m
American Airlines
Mon 3/237:40 am
SJU
-
ANC
2 stops19h 55m
American Airlines
Deal found 1/27$845

Find flight deals from Alaska to Caribbean

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

Round-trip from

$703
(United Airlines)

One-way from

$319
(United Airlines)

Popular in

May

Cheapest in

August
From Alaska to Caribbean
Search Deals
One-way flight from Alaska to Caribbean
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 Alaska 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 Alaska to Caribbean that are best for you.

Fly from

Alaska

Fly to

Caribbean

Route

Depart

Return

Price

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Thu 7/16

11:59 pm-2:57 pm

1 stop10h 58m

Nassau Intl

Sat 7/25

5:00 pm-11:20 am

2 stops22h 20m

$703

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sun 3/15

9:10 pm-3:22 pm

1 stop14h 12m

Nassau Intl

Sun 3/22

1:05 pm-8:01 pm

2 stops34h 56m

$737

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sun 3/29

9:04 pm-12:03 pm

2 stops34h 59m

Nassau Intl

Wed 4/1

2:53 pm-10:45 pm

2 stops35h 52m

$750

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Sun 3/15

11:52 pm-8:00 pm

2 stops16h 08m

San Juan Luis Munoz Marin Intl

Tue 3/24

7:05 am-8:01 pm

2 stops16h 56m

$765

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Mon 3/16

11:52 pm-8:00 pm

2 stops16h 08m

San Juan Luis Munoz Marin Intl

Wed 3/25

7:05 am-8:01 pm

2 stops16h 56m

$765

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Mon 3/30

9:04 pm-2:44 pm

1 stop13h 40m

San Juan Luis Munoz Marin Intl

Fri 4/17

1:40 pm-10:45 pm

1 stop13h 05m

$765

FairbanksSan Juan

FAI - SJU

FAISJU

Fairbanks

Mon 5/4

8:55 pm-9:24 pm

2 stops20h 29m

San Juan Luis Munoz Marin Intl

Wed 5/6

4:55 pm-7:42 pm

2 stops30h 47m

$785

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Sat 2/21

9:00 am-1:17 pm

2 stops23h 17m

San Juan Luis Munoz Marin Intl

Thu 3/5

2:25 pm-10:50 pm

1 stop13h 25m

$790

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Mon 5/4

9:00 pm-9:24 pm

2 stops20h 24m

San Juan Luis Munoz Marin Intl

Wed 5/6

4:55 pm-5:01 pm

2 stops28h 06m

$794

FairbanksSan Juan

FAI - SJU

FAISJU

Fairbanks

Mon 4/20

3:53 pm-3:08 pm

2 stops19h 15m

San Juan Luis Munoz Marin Intl

Fri 5/1

11:38 am-1:42 am

2 stops18h 04m

$846

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

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

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

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

Currently, February is the cheapest month in which you can book a flight from Alaska to Caribbean (average of $380). Flying from Alaska to Caribbean in January is currently the most expensive (average of $1,006). 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 Alaska to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Alaska to Caribbean?

    United Airlines, American Airlines, and Air Canada can get you from Alaska to Caribbean in just under 10h 58m. Your travel time can differ by up to 25h 33m. Airlines will cover a distance of 4133 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Alaska to Caribbean 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.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Alaska 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 Alaska to Caribbean?

    Currently, February is the cheapest month in which you can book a flight from Alaska to Caribbean (average of $380). Flying from Alaska to Caribbean in January is currently the most expensive (average of $1,006). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Alaska to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
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Top 2 airlines flying from Alaska to Caribbean

Discover the top 2 airlines that operate flights from Alaska to Caribbean. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$956FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$448Average$994FlexibilityNo cancel feeOn-time69%

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