HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Alaska

$318+ Cheap flights from Caribbean Islands 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 7/29. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ANC
Mar 6 — Mar 131
Fri 3/6
Fri 3/13
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Caribbean Islands to Alaska with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Caribbean Islands to Alaska

Cheapest flights from Caribbean Islands to Alaska
Explore the most affordable flight options available from Caribbean Islands to Alaska. 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 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.
Tue 3/107:05 am
SJU
-
ANC
2 stops19h 45m
United Airlines
Tue 3/179:10 pm
ANC
-
SJU
2 stops20h 12m
United Airlines
Deal found 2/4$736
This Delta deal was found by Cheapflights users on 2/1. 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.
Tue 4/76:15 am
SJU
-
ANC
2 stops16h 36m
Delta
Mon 4/133:45 pm
ANC
-
SJU
2 stops16h 27m
Delta
Deal found 2/1$766
This Delta deal was found by Cheapflights users on 2/1. 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.
Wed 4/157:15 am
SJU
-
ANC
2 stops21h 10m
Delta
Sat 4/258:25 pm
ANC
-
SJU
1 stop11h 25m
Delta
Deal found 2/1$785
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:15 am
SJU
-
ANC
1 stop16h 34m
Delta
Wed 5/63:45 pm
ANC
-
SJU
2 stops16h 01m
Delta
Deal found 2/4$786
This Delta deal was found by Cheapflights users on 2/1. 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.
Wed 4/86:15 am
SJU
-
ANC
2 stops16h 36m
Delta
Mon 4/133:45 pm
ANC
-
SJU
2 stops16h 05m
Delta
Deal found 2/1$806
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 4/97:20 am
SJU
-
ANC
2 stops16h 35m
United Airlines
Tue 4/149:04 pm
ANC
-
SJU
2 stops20h 20m
United Airlines
Deal found 2/1$811
This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/154:20 pm
SJU
-
ANC
1 stop31h 28m
Sun Country Air
Fri 7/311:22 pm
ANC
-
SJU
1 stop21h 56m
Sun Country Air
Deal found 2/2$813
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 6/251:40 pm
SJU
-
FAI
1 stop13h 09m
United Airlines
Mon 6/291:15 am
FAI
-
SJU
2 stops15h 19m
United Airlines
Deal found 2/1$825
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 4/101:40 pm
SJU
-
ANC
1 stop13h 05m
United Airlines
Fri 4/249:04 pm
ANC
-
SJU
2 stops20h 20m
United Airlines
Deal found 2/1$826
This Delta deal was found by Cheapflights users on 2/1. 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.
Sat 4/116:15 am
SJU
-
ANC
1 stop16h 46m
Delta
Tue 4/213:45 pm
ANC
-
SJU
2 stops16h 05m
Delta
Deal found 2/1$831
This United Airlines deal was found by Cheapflights users on 2/1. 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.
Fri 4/101:40 pm
SJU
-
ANC
1 stop13h 05m
United Airlines
Sun 4/2611:47 pm
ANC
-
SJU
2 stops32h 47m
United Airlines
Deal found 2/1$838
This United Airlines deal was found by Cheapflights users on 2/1. 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 4/71:40 pm
SJU
-
ANC
1 stop13h 05m
United Airlines
Fri 4/109:04 pm
ANC
-
SJU
2 stops20h 20m
United Airlines
Deal found 2/1$841

Find flight deals from Caribbean Islands to Alaska

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

Round-trip from

$736
(United Airlines)

One-way from

$318
(Sun Country Air)
From Caribbean Islands to Alaska
Search Deals
One-way flight from Caribbean Islands to Alaska
Search Deals

Cheapflights Fare Finder

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

Fly from

Caribbean Islands

Fly to

Alaska

Route

Depart

Return

Price

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Wed 4/15

6:15 am-8:37 pm

2 stops18h 22m

Anchorage

Mon 4/20

1:44 pm-12:52 pm

2 stops19h 08m

$766

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Tue 4/7

6:15 am-6:51 pm

2 stops16h 36m

Anchorage

Wed 4/15

3:45 pm-12:52 pm

2 stops17h 07m

$766

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Wed 4/15

6:15 am-8:37 pm

2 stops18h 22m

Anchorage

Wed 4/22

3:45 pm-12:52 pm

2 stops17h 07m

$766

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Thu 4/16

6:15 am-8:37 pm

2 stops18h 22m

Anchorage

Fri 4/24

9:15 pm-3:12 pm

1 stop13h 57m

$785

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Sat 5/2

7:30 am-6:49 pm

1 stop15h 19m

Anchorage

Wed 5/6

3:45 pm-1:18 pm

2 stops17h 33m

$786

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Thu 4/16

6:15 am-8:37 pm

2 stops18h 22m

Anchorage

Thu 4/23

1:44 pm-12:52 pm

2 stops19h 08m

$786

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Wed 7/15

4:20 pm-7:48 pm

1 stop31h 28m

Anchorage

Fri 7/31

1:22 pm-3:18 pm

1 stop21h 56m

$813

San JuanFairbanks

SJU - FAI

SJUFAI

San Juan Luis Munoz Marin Intl

Thu 6/25

1:40 pm-10:49 pm

1 stop13h 09m

Fairbanks

Mon 6/29

1:15 am-8:34 pm

2 stops15h 19m

$825

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Tue 4/14

7:20 am-7:55 pm

2 stops16h 35m

Anchorage

Fri 4/24

9:04 pm-9:24 pm

2 stops20h 20m

$826

San JuanAnchorage

SJU - ANC

SJUANC

San Juan Luis Munoz Marin Intl

Tue 4/14

7:20 am-7:55 pm

2 stops16h 35m

Anchorage

Mon 4/20

9:04 pm-9:24 pm

2 stops20h 20m

$826

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/4

Showing 1-10 of 40 results
1
2
3
4

Best time to book a flight from Caribbean Islands to Alaska

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

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

Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Alaska (average of $187). Flying from Caribbean Islands 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 February 4, 2026.
Read through reviews of airlines operating flights from Caribbean Islands to Alaska, such as Delta. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

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
8,146 reviews
Delta
7.9
Good
8,146 reviews

Crew

8.5

Food

7.2

Boarding

8.1

Comfort

7.9

Entertainment

7.8

Overall

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 Caribbean Islands 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 Islands to Alaska?

    A quick flight from Caribbean Islands to Alaska can take about 13h 09m. Delta provides one of the quickest options available for as low as $825. There are 4827 mi between Caribbean Islands and Alaska. This flight may include one or multiple stops.

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

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $428. However, be on the lookout for offers from Delta and Air Canada, as they are both options that can get you from Caribbean Islands to Alaska for a low price.

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

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

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

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

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

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

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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Caribbean Islands to Alaska

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Miami flights
San Francisco to John F Kennedy Intl flights
John F Kennedy Intl to Fort Lauderdale flights
San Francisco to Newark flights
Newark to Fort Lauderdale flights
Newark to Miami flights
LaGuardia to Miami flights
LaGuardia to Fort Lauderdale flights
John F Kennedy Intl to Orlando flights
Newark to West Palm Beach flights
San Francisco to LaGuardia flights
John F Kennedy Intl to West Palm Beach flights
John F Kennedy Intl to Los Angeles flights
John F Kennedy Intl to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
Newark to Las Vegas flights
Newark to Orlando flights
O'Hare Intl to Dallas/Fort Worth flights
Los Angeles to John F Kennedy Intl flights
John F Kennedy Intl to Dallas/Fort Worth flights
Minneapolis to Sky Harbor Intl flights
Seattle to Los Angeles flights
O'Hare Intl to Sky Harbor Intl flights
O'Hare Intl to Las Vegas flights
Seattle to Las Vegas flights
John F Kennedy Intl to Tampa flights
Newark to Tampa flights
Seattle to Sky Harbor Intl flights
Boston to Fort Lauderdale flights
LaGuardia to Orlando flights
LaGuardia to Tampa flights
Los Angeles to Seattle flights
Dulles Intl to Miami flights
Boston to Miami flights
John F Kennedy Intl to San Francisco flights
Reagan-National to Miami flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to LaGuardia flights
O'Hare Intl to Los Angeles flights
John F Kennedy Intl to Sky Harbor Intl flights
John F Kennedy Intl to New Orleans flights
Newark to Sky Harbor Intl flights
Los Angeles to Honolulu flights
Newark to Los Angeles flights
Newark to New Orleans flights
Detroit to Orlando flights
Reagan-National to Orlando flights
San Francisco to Las Vegas flights
Boston to Tampa flights

Top 2 airlines flying from Caribbean Islands to Alaska

Discover the top 2 airlines that operate flights from Caribbean Islands 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 February 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$428Average$765FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$744Average$794FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.