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Alaska

$343+ Cheap flights from Caribbean to Alaska

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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ANC
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Caribbean to Alaska

Cheapest flights from Caribbean to Alaska
Explore the most affordable flight options available from Caribbean to Alaska. 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 1/27. 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 5/27:20 am
SJU
-
ANC
2 stops19h 25m
United Airlines
Wed 5/611:49 pm
ANC
-
SJU
2 stops17h 35m
United Airlines
Deal found 1/27$731
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 5/297:40 am
SJU
-
ANC
2 stops19h 15m
United Airlines
Mon 8/318:35 pm
ANC
-
SJU
1 stop12h 19m
United Airlines
Deal found 1/27$765
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.
Sat 5/27:30 am
SJU
-
ANC
2 stops15h 16m
Delta
Tue 5/51:30 am
ANC
-
SJU
2 stops17h 43m
Delta
Deal found 1/26$786
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 5/286:00 am
SJU
-
ANC
2 stops17h 07m
American Airlines
Thu 6/49:52 pm
ANC
-
SJU
1 stop20h 59m
American Airlines
Deal found 1/27$845
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.
Tue 8/181:05 am
SJU
-
ANC
2 stops22h 40m
United Airlines
Mon 8/2410:30 pm
ANC
-
SJU
1 stop13h 12m
United Airlines
Deal found 1/28$859
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 7/1510:23 am
SJU
-
ANC
2 stops17h 34m
American Airlines
Thu 7/305:00 am
ANC
-
SJU
2 stops15h 17m
American Airlines
Deal found 1/27$867
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.
Sat 5/237:45 am
SJU
-
ANC
2 stops43h 04m
United Airlines
Sun 5/312:15 pm
ANC
-
SJU
3 stops23h 15m
United Airlines
Deal found 1/26$884
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 4/2912:15 am
BQN
-
ANC
2 stops20h 46m
United Airlines
Mon 5/411:59 pm
ANC
-
BQN
2 stops19h 10m
United Airlines
Deal found 1/28$928
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.
Sat 2/148:40 am
SJU
-
FAI
2 stops21h 10m
American Airlines
Tue 2/173:59 pm
FAI
-
SJU
2 stops19h 02m
American Airlines
Deal found 1/26$1,016
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.
Tue 3/245:00 am
SDQ
-
ANC
2 stops19h 01m
United Airlines
Thu 4/99:04 pm
ANC
-
SDQ
2 stops21h 42m
United Airlines
Deal found 1/27$1,017
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/115:55 pm
SDQ
-
ANC
2 stops28h 55m
American Airlines
Mon 8/317:46 pm
ANC
-
SDQ
2 stops18h 34m
American Airlines
Deal found 1/29$1,124
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.
Fri 7/177:00 am
SDQ
-
ANC
2 stops20h 57m
American Airlines
Sun 7/2611:42 pm
ANC
-
SDQ
2 stops19h 17m
American Airlines
Deal found 1/28$1,153

Find flight deals from Caribbean to Alaska

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

Round-trip from

$731
(United Airlines)

One-way from

$343
(Kiwi.com)

Popular in

January

Cheapest in

April

Average price

$1,100
From Caribbean to Alaska
Search Deals
One-way flight from Caribbean to Alaska
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($67 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

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

Fly from

Caribbean

Fly to

Alaska

Route

Depart

Return

Price

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Sat 5/2

7:20 am-10:45 pm

2 stops19h 25m

Anchorage

Wed 5/6

11:49 pm-9:24 pm

2 stops17h 35m

$731

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Fri 5/29

7:40 am-10:55 pm

2 stops19h 15m

Anchorage

Mon 8/31

8:35 pm-12:54 pm

1 stop12h 19m

$765

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Sat 5/2

7:30 am-6:49 pm

1 stop15h 19m

Anchorage

Tue 5/5

1:30 am-11:13 pm

2 stops17h 43m

$786

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Thu 5/28

5:37 am-7:07 pm

1 stop17h 30m

Anchorage

Thu 6/4

9:52 pm-10:51 pm

1 stop20h 59m

$845

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Thu 5/28

12:39 am-7:07 pm

1 stop22h 28m

Anchorage

Mon 8/31

9:55 pm-2:10 pm

1 stop12h 15m

$845

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Wed 7/15

10:23 am-11:57 pm

2 stops17h 34m

Anchorage

Thu 7/30

5:00 am-11:16 pm

2 stops14h 16m

$867

AguadillaAnchorage

BQN - ANC

BQNANC

Aguadilla Borinquen

Wed 4/29

12:15 am-5:01 pm

2 stops20h 46m

Anchorage

Mon 5/4

11:59 pm-11:09 pm

2 stops19h 10m

$928

San JuanFairbanks

SJU - FAI

SJUFAI

San Juan Luis Munoz Marin Intl

Sat 2/14

8:40 am-12:50 am

2 stops21h 10m

Fairbanks

Tue 2/17

3:59 pm-4:01 pm

2 stops19h 02m

$1,016

Santo DomingoAnchorage

SDQ - ANC

SDQANC

Santo Domingo Las Americas

Tue 3/24

5:00 am-8:01 pm

2 stops19h 01m

Anchorage

Thu 4/9

9:04 pm-10:46 pm

2 stops21h 42m

$1,017

Santo DomingoAnchorage

SDQ - ANC

SDQANC

Santo Domingo Las Americas

Mon 5/11

5:55 pm-6:50 pm

2 stops28h 55m

Anchorage

Mon 8/31

7:46 pm-6:20 pm

2 stops18h 34m

$1,124

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 33 results
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Best time to book a flight from Caribbean to Alaska

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean to Alaska (average of $187). Flying from Caribbean to Alaska in March is currently the most expensive (average of $966). 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 Alaska

Get insights into the airlines that provide service to Alaska. 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 Alaska. Reviews last updated January 29, 2026.
Get a feel of what it's like to fly with Delta and United Airlines from Caribbean to Alaska by reading reviews from past customers. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,128 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.8

Food

7.2

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
8,128 reviews
Delta
7.9
Good
8,128 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.8

Food

7.2

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.
United Airlines
7.4
Good
9,215 reviews
Delta
7.9
Good
8,128 reviews

Comfort

7.9

Crew

8.5

Boarding

8.1

Overall

7.9

Entertainment

7.8

Food

7.2

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 Caribbean to Alaska. 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 Caribbean to Alaska?

    Airlines like United Airlines, Delta, and American Airlines fly from Caribbean to Alaska in about 15h 19m. The time it takes to get you to your destination can typically vary by up to 5h 51m. Caribbean and Alaska are separated by a distance of 4905 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    The cheapest airlines for a one-way flight from Caribbean to Alaska are United Airlines ($428), Delta ($572), and Air Canada ($578).

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Alaska (average of $187). Flying from Caribbean to Alaska in March is currently the most expensive (average of $966). 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 Caribbean to Alaska

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

Discover the top 2 airlines that operate flights from Caribbean to Alaska. 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$428Average$765FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$744Average$794FlexibilityNo cancel feeOn-time69%

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