Caribbean Islands

$253+ Cheap flights from Alaska 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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
ANC — SJU
Mar 6 — Mar 131
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Cheap flight deals from Alaska to Caribbean Islands

Cheapest flights from Alaska to Caribbean Islands
Explore the most affordable flight options available from Alaska to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.

This United Airlines deal was found by Cheapflights users on 1/31. 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 5/1611:59 pm
ANC
-
NAS
1 stop10h 58m
United Airlines
Sun 5/242:53 pm
NAS
-
ANC
2 stops24h 17m
United Airlines
Deal found 1/31$664
This United Airlines deal was found by Cheapflights users on 2/4. 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 3/239:10 pm
ANC
-
NAS
2 stops13h 22m
United Airlines
Mon 3/301:15 pm
NAS
-
ANC
2 stops34h 40m
United Airlines
Deal found 2/4$753
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 3/211:45 pm
ANC
-
SJU
2 stops17h 37m
United Airlines
Mon 3/97:05 am
SJU
-
ANC
2 stops16h 56m
United Airlines
Deal found 2/2$765
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/269:00 am
ANC
-
NAS
2 stops22h 53m
United Airlines
Tue 3/33:35 pm
NAS
-
ANC
2 stops35h 33m
United Airlines
Deal found 2/3$774
This United Airlines deal was found by Cheapflights users on 2/4. 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 3/2111:52 pm
ANC
-
NAS
2 stops57h 41m
United Airlines
Mon 3/301:15 pm
NAS
-
ANC
2 stops37h 30m
United Airlines
Deal found 2/4$782
This United Airlines deal was found by Cheapflights users on 2/3. 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 2/3$785
This United Airlines deal was found by Cheapflights users on 2/2. 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.
Mon 5/49:00 pm
ANC
-
SJU
2 stops20h 24m
United Airlines
Wed 5/64:55 pm
SJU
-
ANC
2 stops28h 06m
United Airlines
Deal found 2/2$794
This Delta deal was found by Cheapflights users on 2/3. 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 3/223:40 pm
ANC
-
SJU
2 stops18h 35m
Delta
Thu 4/26:15 am
SJU
-
ANC
2 stops16h 36m
Delta
Deal found 2/3$810
This United Airlines deal was found by Cheapflights users on 2/3. 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 3/229:10 pm
ANC
-
SJU
1 stop13h 30m
United Airlines
Thu 4/21:40 pm
SJU
-
ANC
1 stop13h 05m
United Airlines
Deal found 2/3$816
This American Airlines deal was found by Cheapflights users on 2/2. 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.
Wed 3/2512:59 am
ANC
-
SJU
2 stops17h 32m
American Airlines
Fri 4/36:33 am
SJU
-
ANC
2 stops18h 05m
American Airlines
Deal found 2/2$845
This United Airlines deal was found by Cheapflights users on 2/3. 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 3/111:45 pm
ANC
-
SJU
2 stops34h 55m
United Airlines
Tue 3/107:05 am
SJU
-
ANC
2 stops19h 45m
United Airlines
Deal found 2/3$847
This Delta deal was found by Cheapflights users on 2/3. 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 3/107:30 am
SJU
-
ANC
2 stops20h 58m
Delta
Deal found 2/3$855

Find flight deals from Alaska to Caribbean Islands

Keep the following information in mind while searching for Alaska to Caribbean Islands flight deals. Data was last updated February 4, 2026.

Round-trip from

$753
(United Airlines)

One-way from

$253
(United Airlines)

Popular in

July

Cheapest in

August

Average price

$998
From Alaska to Caribbean Islands
One-way flight from Alaska to Caribbean Islands
High demand for flights, 2% potential price rise
Cheapest flight prices on average. 1% potential price decrease ($16 potential savings vs. average RT price).
Average for round-trip flights in February 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Alaska 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 February 4, 2026.
Use the filters below to find and compare flights from Alaska to Caribbean Islands that are best for you.

Fly from

Alaska

Fly to

Caribbean Islands

Route

Depart

Return

Price

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sat 5/16

11:59 pm-2:57 pm

1 stop10h 58m

Nassau Intl

Sun 5/24

2:53 pm-11:10 am

2 stops24h 17m

$664

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sun 3/22

9:10 pm-2:32 pm

2 stops13h 22m

Nassau Intl

Mon 3/30

1:15 pm-7:55 pm

2 stops34h 40m

$753

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Mon 3/23

9:10 pm-3:22 pm

1 stop14h 12m

Nassau Intl

Mon 3/30

1:15 pm-10:45 pm

2 stops37h 30m

$753

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Tue 3/24

9:10 pm-2:32 pm

2 stops13h 22m

Nassau Intl

Mon 3/30

1:15 pm-7:55 pm

2 stops34h 40m

$753

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Wed 3/18

3:40 pm-12:54 pm

2 stops17h 14m

San Juan Luis Munoz Marin Intl

Tue 3/24

6:15 am-6:51 pm

2 stops16h 36m

$765

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Mon 3/2

11:45 pm-10:22 pm

2 stops17h 37m

San Juan Luis Munoz Marin Intl

Mon 3/9

7:05 am-8:01 pm

2 stops16h 56m

$765

AnchorageSan Juan

ANC - SJU

ANCSJU

Anchorage

Sun 3/22

11:52 pm-8:00 pm

2 stops16h 08m

San Juan Luis Munoz Marin Intl

Thu 4/2

1:40 pm-10:45 pm

1 stop13h 05m

$765

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Thu 2/26

9:00 am-11:53 am

2 stops22h 53m

Nassau Intl

Tue 3/3

3:35 pm-11:08 pm

2 stops35h 33m

$774

AnchorageNassau

ANC - NAS

ANCNAS

Anchorage

Sat 3/21

11:52 pm-1:33 pm

2 stops57h 41m

Nassau Intl

Mon 3/30

1:15 pm-10:45 pm

2 stops37h 30m

$782

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

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/31

Showing 1-10 of 53 results
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Best time to book a flight from Alaska to Caribbean Islands

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

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

Currently, February is the cheapest month in which you can book a flight from Alaska to Caribbean Islands (average of $380). Flying from Alaska to Caribbean Islands 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 Islands. 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 Islands?

    For as low as $664, United Airlines can have you in Caribbean Islands from Alaska in 10h 58m. There are 4133 mi between Alaska and Caribbean Islands. 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 Islands one-way?

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as $365. However, be on the lookout for offers from Delta and United Airlines, as they are both options that can get you from Alaska to Caribbean Islands for a low price.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Alaska to Caribbean Islands (average of $380). Flying from Alaska to Caribbean Islands 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 Islands

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Alaska to Caribbean Islands

Discover the top 2 airlines that operate flights from Alaska 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$268Average$971FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$448Average$992FlexibilityNo cancel feeOn-time69%

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