$342 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 4/24. 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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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$866
Santo Domingo
Santo Domingo2 stops$942
Nassau
Nassau1 stop$857
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,162
Saint Thomas Island
Saint Thomas Island2 stops$1,190
Kingston
Kingston2 stops$1,197
Punta Cana
Punta Cana1 stop$866
Santo Domingo
Santo Domingo2 stops$942
Nassau
Nassau1 stop$857
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,162
Saint Thomas Island
Saint Thomas Island2 stops$1,190
Kingston
Kingston2 stops$1,197

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

Thu, Apr 30 - Thu, May 7
United Airlines Logo
11:59 pm - 9:24 pm
ANC
-
SJU
17h 25m
2 stops
United Airlines Logo
7:40 am - 5:01 pm
SJU
-
ANC
13h 21m
1 stop
$815United Airlines
Sun, Apr 26 - Wed, Apr 29
United Airlines Logo
8:50 pm - 8:34 pm
ANC
-
SJU
19h 44m
1 stop
United Airlines Logo
1:00 am - 5:01 pm
SJU
-
ANC
20h 01m
2 stops
$844United 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 - 10:45 pm
NAS
-
ANC
34h 46m
2 stops
$857United Airlines
Fri, May 15 - Fri, May 22
Multiple Airlines Logo
11:08 pm - 5:57 pm
ANC
-
PUJ
14h 49m
1 stop
Multiple Airlines Logo
9:29 pm - 11:53 am
PUJ
-
ANC
42h 24m
2 stops
$866Multiple Airlines
Tue, Jun 2 - Tue, Jul 21
American Airlines Logo
9:53 pm - 11:59 pm
ANC
-
SJU
22h 06m
1 stop
American Airlines Logo
10:33 am - 11:59 pm
SJU
-
ANC
17h 26m
2 stops
$895American Airlines
Sat, May 16 - Sun, May 24
American Airlines Logo
8:30 pm - 4:28 pm
ANC
-
NAS
15h 58m
2 stops
American Airlines Logo
8:00 am - 11:52 pm
NAS
-
ANC
19h 52m
2 stops
$909American Airlines
Sun, Jun 7 - Sun, Jun 21
Southwest Logo
10:25 pm - 7:25 pm
ANC
-
SJU
17h 00m
2 stops
Southwest Logo
6:05 am - 9:15 pm
SJU
-
ANC
19h 10m
2 stops
$965Southwest
Sat, May 30 - Sat, Jun 13
Multiple Airlines Logo
2:25 am - 9:45 pm
ANC
-
SDQ
15h 20m
2 stops
Multiple Airlines Logo
6:10 am - 1:30 pm
SDQ
-
ANC
35h 20m
1 stop
$992Multiple Airlines
Sat, Apr 18 - Sun, May 3
Delta Logo
8:25 pm - 11:45 am
ANC
-
SJU
11h 20m
1 stop
Delta Logo
7:15 am - 12:25 am
SJU
-
ANC
21h 10m
2 stops
$995Delta
Thu, Jun 4 - Tue, Jun 16
Delta Logo
8:05 pm - 1:23 pm
ANC
-
SDQ
13h 18m
1 stop
Delta Logo
6:06 am - 9:16 pm
SDQ
-
ANC
19h 10m
2 stops
$1,162Delta
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 $627, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonAugust
Cheapest flight$342
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 Punta Cana

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 8368 reviews
8.5Crew
7.2Food
7.9Comfort
8.1Boarding
7.8Entertainment
Airline reviews

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

10.0 ExcellentAnonymous, Mar 2026
SAT - LAX
Read more Delta reviews

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

The flight was delayed 90 minutes The Gate was wrong The Restroom on Aircraft was not clean There was a half used water bottle in my seat

Delta is always a wonderful experience. A clean plane and the crew is really friendly.

Too many people are taking up space in the overhead bins with their extra piece of luggage. Since they cannot fit their backpacks or extra luggage piece under the seat in front of them, they store it in the overheads and thus taking up room for other passengers. It wasn’t only one or two persons; more like 12 or 13 passengers.

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Anchorage (ANC)