$359 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 2/16. 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$1,036
Santo Domingo
Santo Domingo2 stops$1,021
Nassau
Nassau2 stops$613
Saint Thomas Island
Saint Thomas Island2 stops$1,136
Kingston
Kingston2 stops$1,932
Puerto Plata
Puerto Plata2 stops$1,085
Punta Cana
Punta Cana1 stop$1,036
Santo Domingo
Santo Domingo2 stops$1,021
Nassau
Nassau2 stops$613
Saint Thomas Island
Saint Thomas Island2 stops$1,136
Kingston
Kingston2 stops$1,932
Puerto Plata
Puerto Plata2 stops$1,085

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

週一, 2月 2 - 週五, 2月 6
United Airlines Logo
9:00 am - 11:53 am
ANC
-
NAS
22h 53m2 stops
United Airlines Logo
3:35 pm - 11:15 pm
NAS
-
ANC
35h 40m2 stops
$613United Airlines
週一, 1月 19 - 週一, 1月 26
United Airlines Logo
9:00 am - 3:22 pm
ANC
-
NAS
26h 22m2 stops
United Airlines Logo
4:25 pm - 11:15 pm
NAS
-
ANC
34h 50m2 stops
$623United Airlines
週三, 1月 21 - 週四, 1月 29
United Airlines Logo
9:00 am - 11:53 am
ANC
-
NAS
22h 53m2 stops
United Airlines Logo
3:35 pm - 11:15 pm
NAS
-
ANC
35h 40m2 stops
$659United Airlines
週二, 4月 14 - 週二, 4月 21
American Airlines Logo
1:50 am - 7:45 pm
ANC
-
SJU
13h 55m2 stops
American Airlines Logo
6:59 am - 6:35 pm
SJU
-
ANC
15h 36m1 stop
$824American Airlines
週四, 12月 25 - 週六, 1月 17
Delta Logo
5:45 am - 2:27 am
ANC
-
SJU
15h 42m2 stops
Delta Logo
6:15 am - 6:56 pm
SJU
-
ANC
17h 41m2 stops
$979Delta
週二, 4月 14 - 週二, 4月 21
Alaska Airlines Logo
1:30 am - 4:00 am
ANC
-
SJU
22h 30m3 stops
Alaska Airlines Logo
6:59 am - 10:29 pm
SJU
-
ANC
19h 30m2 stops
$1,044Alaska Airlines
週五, 3月 27 - 週四, 4月 16
American Airlines Logo
8:13 pm - 8:29 pm
ANC
-
STI
20h 16m2 stops
American Airlines Logo
3:35 pm - 6:35 pm
STI
-
ANC
31h 00m2 stops
$1,051American Airlines
週五, 1月 9 - 週五, 1月 16
Multiple Airlines Logo
10:05 am - 1:23 pm
ANC
-
POP
22h 18m2 stops
Multiple Airlines Logo
4:42 pm - 2:17 pm
POP
-
ANC
26h 35m3 stops
$1,356Multiple Airlines
週一, 12月 29 - 週三, 1月 7
Multiple Airlines Logo
8:30 pm - 5:27 pm
ANC
-
STI
15h 57m2 stops
Multiple Airlines Logo
4:33 pm - 11:56 am
STI
-
ANC
24h 23m2 stops
$1,436Multiple Airlines
週二, 12月 23 - 週二, 12月 30
Delta Logo
3:40 pm - 12:58 pm
ANC
-
STI
16h 18m2 stops
Delta Logo
8:45 pm - 2:45 pm
STI
-
ANC
23h 00m2 stops
$1,661Delta
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 $635, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Anchorage to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Anchorage to Caribbean Islands is August, when tickets cost $441 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $1,246 and $1,079 respectively.

What’s the cheapest day of the week to fly from Anchorage to Caribbean Islands?

The average price of all round-trip flights from Anchorage to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Anchorage to Caribbean Islands, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Anchorage, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

Good to know

Low seasonAugust
Cheapest flight$359
Best time to beat the crowds with an average 56% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $1,008 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,242.

Reviews of the top airlines 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.
8.0
Alaska AirlinesOverall score based on 11408 reviews
7.1Food
8.5Crew
7.0Entertainment
7.8Comfort
8.1Boarding
Airline reviews

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

2.0 MediocreAnonymous, Oct 2025
ANC - LAS
Read more Alaska Airlines reviews

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

My flight was canceled because of an IT outage, and they did not answer the phone for 8 hrs. There was no next flight out, I have missed my wedding because of this.

Liked the crew. Multiple delays. Altered my complete day and plans

The plane was clean. They got us to the destination. It was very difficult to hear the announcements at the gate. The person was speaking way too quickly, and the sound system did not carry to all parts of the seating area at the gate. The flight left more than an hour late, which left many of the passengers missing connections.

The chicken salad was very small, the lettuce was wilted and there was no flavor. The hamburger was excellent.

Mostly good. Delayed which in my experience so far happens often with Alaska Airlines. Thank you.

We received a check-in reminder the day before the flight, and it listed the flight at a later time. Correct flight number, same seats, etc. for 3 hours later. I called the airline to confirm and they had no record of the email. The info was wrong, and we would have missed our flight if we'd assumed it was correct. I want to know where/how we received this incorrect info.

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

5 1/2 hour trip. Nice plane. easy boarding. Could have used a bit more beverage service but it was a red eye flight and they didn't want to wake everyone.

Paid extra $230 to check frozen fish on arrival to LAX. I was told my bags miss my flight and we’re gonna be on the next flight that comes in two hours later regrettably my family was here to pick me up so I had to drive all the way home to drop them off then turn around and come back if I had waited on Alaska to deliver them they told me that they would be delivered in 4 to 6 hours after 8 AM tomorrow which would’ve caused the fish to spoil stink and be a lost cause they would’ve put about $2500 worth of fish down the drain very unhappy with Alaska Airlines for not getting my baggage here, especially since I had to pay for the extra service

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports