$338 Find Cheap Flights from Anchorage to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Anchorage to Caribbean Islands departing on 7/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Anchorage to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$1,022
Santo Domingo
Santo Domingo2 stops$1,002
Nassau
Nassau1 stop$709
Saint Thomas Island
Saint Thomas Island2 stops$1,109
Kingston
Kingston2 stops$1,197
Puerto Plata
Puerto Plata2 stops$1,032
Punta Cana
Punta Cana1 stop$1,022
Santo Domingo
Santo Domingo2 stops$1,002
Nassau
Nassau1 stop$709
Saint Thomas Island
Saint Thomas Island2 stops$1,109
Kingston
Kingston2 stops$1,197
Puerto Plata
Puerto Plata2 stops$1,032

Book Cheap Anchorage to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Anchorage to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Anchorage to Caribbean Islands

Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
8:17 pm - 5:05 pm
ANC
-
NAS
16h 48m
1 stop
American Airlines Logo
11:03 am - 11:52 pm
NAS
-
ANC
16h 49m
2 stops
$709American Airlines
Tue, Sep 1 - Thu, Oct 1
United Airlines Logo
3:10 pm - 11:57 am
ANC
-
SJU
16h 47m
2 stops
United Airlines Logo
2:00 pm - 10:39 pm
SJU
-
ANC
12h 39m
1 stop
$815United Airlines
Sun, Apr 19 - Sun, Apr 26
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
2:53 pm - 7:48 pm
NAS
-
ANC
32h 55m
2 stops
$822United Airlines
Sun, Apr 26 - Wed, Apr 29
United Airlines Logo
8:50 pm - 9:24 pm
ANC
-
SJU
20h 34m
2 stops
United Airlines Logo
1:00 am - 5:01 pm
SJU
-
ANC
20h 01m
2 stops
$834United Airlines
Thu, Sep 17 - Sat, Sep 19
United Airlines Logo
3:30 pm - 3:42 pm
ANC
-
SJU
20h 12m
2 stops
United Airlines Logo
1:00 am - 3:04 pm
SJU
-
ANC
18h 04m
2 stops
$835United Airlines
Sat, Apr 25 - Wed, Apr 29
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:59 pm - 5:01 pm
NAS
-
ANC
29h 02m
1 stop
$837United Airlines
Tue, Apr 21 - Tue, Apr 28
United Airlines Logo
11:47 pm - 8:38 pm
ANC
-
SJU
16h 51m
2 stops
United Airlines Logo
1:40 pm - 10:45 pm
SJU
-
ANC
13h 05m
1 stop
$839United Airlines
Sat, Apr 18 - Sun, May 3
Delta Logo
1:41 pm - 12:12 pm
ANC
-
SJU
18h 31m
2 stops
Delta Logo
7:30 am - 12:25 am
SJU
-
ANC
20h 55m
2 stops
$855Delta
Tue, Apr 21 - Tue, Apr 28
Delta Logo
1:41 pm - 11:45 am
ANC
-
SJU
18h 04m
2 stops
Delta Logo
7:15 am - 12:25 am
SJU
-
ANC
21h 10m
2 stops
$860Delta
Sun, Sep 20 - Thu, Sep 24
Air Canada Logo
2:40 pm - 1:55 pm
ANC
-
KIN
44h 15m
2 stops
Air Canada Logo
11:35 am - 1:35 pm
KIN
-
ANC
29h 00m
2 stops
$1,258Air Canada
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean Islands flights

Get data-powered insights and trends into flights from Anchorage to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Anchorage to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $625, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$338
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Anchorage to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Anchorage to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Anchorage to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Anchorage to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Anchorage to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Anchorage to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Anchorage to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Anchorage to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Anchorage to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Anchorage to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Anchorage to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Anchorage to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8320 reviews
7.8Entertainment
7.2Food
8.5Crew
7.9Comfort
8.1Boarding
Airline reviews

The cabin temperature was nice and cool. The wifi was not working.

8.0 ExcellentMatt, Mar 2026
SEA - SJC
Read more Delta reviews

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

Entertainment is ok! Boarding and seat with zone is terrible. I paid for the seats but you didn’t give me what I paid for which is exit isles.

the crew cancel the morning service due to the weather. Then the flight got deverted to Nashville . we were on the ground for over two hours the only gave us water once... no food or any snacks.... the crew should have handled better and offered something to passengers.

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports