$421 Find Cheap Flights from Anchorage to Caribbean - Compare and Save

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 departing on 8/29. 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

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Anchorage to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$853
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$767
Saint Thomas Island
Saint Thomas Island2 stops$1,290
Kingston
Kingston2 stops$1,407
Puerto Plata
Puerto Plata2 stops$1,338
Punta Cana
Punta Cana2 stops$853
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$767
Saint Thomas Island
Saint Thomas Island2 stops$1,290
Kingston
Kingston2 stops$1,407
Puerto Plata
Puerto Plata2 stops$1,338

Book Cheap Anchorage to Caribbean 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 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

Thu, Sep 17 - Thu, Sep 24
American Airlines Logo
9:54 pm - 5:55 pm
ANC
-
NAS
16h 01m
2 stops
American Airlines Logo
10:32 am - 8:49 pm
NAS
-
ANC
14h 17m
2 stops
$767American Airlines
Wed, Aug 26 - Wed, Sep 2
United Airlines Logo
8:00 pm - 1:33 pm
ANC
-
NAS
13h 33m
2 stops
United Airlines Logo
12:35 pm - 11:59 pm
NAS
-
ANC
15h 24m
2 stops
$795United Airlines
Mon, Aug 31 - Mon, Sep 7
United Airlines Logo
8:19 pm - 11:57 am
ANC
-
SJU
11h 38m
1 stop
United Airlines Logo
7:00 am - 7:02 pm
SJU
-
ANC
16h 02m
1 stop
$815United Airlines
Mon, Aug 31 - Sun, Sep 6
United Airlines Logo
11:09 pm - 8:38 pm
ANC
-
SJU
17h 29m
2 stops
United Airlines Logo
1:00 am - 1:04 pm
SJU
-
ANC
16h 04m
2 stops
$815United Airlines
Sun, Aug 30 - Sun, Sep 6
Southwest Logo
10:25 pm - 10:50 pm
ANC
-
SJU
20h 25m
2 stops
Southwest Logo
5:20 am - 9:15 pm
SJU
-
ANC
19h 55m
2 stops
$830Southwest
Wed, Aug 26 - Thu, Sep 3
Multiple Airlines Logo
2:28 am - 7:54 pm
ANC
-
PUJ
37h 26m
2 stops
Multiple Airlines Logo
7:30 pm - 11:12 am
PUJ
-
ANC
19h 42m
1 stop
$853Multiple Airlines
Wed, Jan 6 - Mon, Jan 18
Delta Logo
5:15 pm - 2:05 pm
ANC
-
SJU
15h 50m
2 stops
Delta Logo
6:15 am - 9:03 pm
SJU
-
ANC
19h 48m
2 stops
$885Delta
Fri, Jan 8 - Sat, Jan 16
Delta Logo
9:55 pm - 2:15 pm
ANC
-
SJU
11h 20m
1 stop
Delta Logo
7:00 am - 9:03 pm
SJU
-
ANC
19h 03m
2 stops
$885Delta
Fri, Nov 6 - Sat, Nov 14
American Airlines Logo
8:14 pm - 3:59 pm
ANC
-
SDQ
14h 45m
2 stops
American Airlines Logo
6:00 am - 7:09 pm
SDQ
-
ANC
18h 09m
2 stops
$993American Airlines
Sun, Aug 23 - Thu, Aug 27
American Airlines Logo
8:20 pm - 8:43 pm
ANC
-
STX
20h 23m
2 stops
American Airlines Logo
8:30 am - 10:32 pm
STX
-
ANC
18h 02m
2 stops
$999American Airlines
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean flights

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean, 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 is August, when tickets cost $602 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $1,192 and $1,161 respectively.

Good to know

Low season

April

Cheapest flight

$421
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from Anchorage to Punta Cana

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Anchorage to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Anchorage to Caribbean

 
Need help choosing which airline to fly with from Anchorage to Caribbean? 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.
7.8
DeltaOverall score based on 8483 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

4.0 OkayNoel, Aug 2026
LAS - BOS
Read more Delta reviews

My experience with Delta started with my luggage being found ripped open with items missing. The baggage office told me to bring the bag, and I wanted them to see how I found it. The agent refused, so I carried my bag into the office myself. The agent was nice enough to fix the zipper and gave me a red card with a number to call. I followed the steps; first one department, then the baggage department took over. This took more than two hours on the phone. The return flight was okay. The flight lead was checking her meals and then asked if we wanted anything before departure. However, throughout the flight, I had to ask for things because she was reading her book;which I have no issue with if she had been more attentive. At the end of the flight, the pilot appeared annoyed with the flight lead for not following his instructions regarding a meal he had requested; a chicken sandwichand said, "I asked for that for the flight." On the positive side, my work event in Vegas went well, and now I'm home relaxing.

Internet connectivity still seems to be touchy on these flights, making it difficult to rely on it for getting work done.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Lounge in Lagos is terrible, food on board from Lagos to Atlanta was horrible. Only bright spot the cabin crew were awesome.

No one fussed at me about my pap machine as a 3rd pice on the plane. Boarding was pleasant and smooth. The boarding agent in Anchorage was a fun character- he could be in a movie. :~) The on-board crew were downright pleasant. No militant attitudes on Delta. Like all planes these days the seats are too narrow for standard Americans and at 5’2” there is barely enough leg room. I don’t know how tall people fold themselves into the seats. But that’s nothing specific to Delta

Food from the flight from Atlanta to Santiago was very poor..

Delta was great the entertainment was outdated. Screen was very small and didn’t work.

The boarding was great. With all the delays I was grateful to get on the plane and headed for home. There was no in flight entertainment. Seats were very uncomfortable! Unfortunately we were seated next to an exit row so there was no recline in our seat. Other than that it was a smooth ride.

It was pretty good I was worried with the short Layover that I might not catch my connection but the gate was there

Delta is one of the best airlines I have flown

Flight staff and all was fine. Food always sucks on planes so nothing new.

The flight crew were very helpful. The seats were very close together. There was barely room to sit without touching the person next to you.

I’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

There was no food available for this red eye... one little waffle cookie for a 6+ hour flight... thank God I was able to sleep some

To san Francisco it was ok. From sf to Manila it was horrible

You have got to come up with a better way of getting connecting flight people off the plane first. Flying doesn’t bring out the best in people but exiting off a plane rules needs to come from management, not from the expectation that passengers will be “kind” and let them off first. Perhaps exiting in zones? Like boarding? Zone 1 exits are connecting people. This frustration led to many people missing their flights or scrambling. We were delayed leaving the first leg which amplified this.

The flight was delayed 4 hours, and when we finally boarded, they told us that the fuel was only just then checked. So, we waited even longer to take off.

With a 24 hour delay, the Flight stared off rough. They had a nationwide IT Outage but communications to Passengers was very bad. Ground Staff and Ticket Agents were extremely rude and unhelpful. Perhaps they should take ground training from DL or Qatar. The food was horrible. Seafood was mixed with Bacon. Those two don’t have any space for Jewish or Muslim Faith Customers. The Airline needs new management.

Great. Clean. Seats comfortable. Food was free. Had new release movies.

The airplane I love and I love I came back safe thank you American airlines

Although there were two delays, they were communicated clearly and the boarding process was expedited. The crew was pleasant and efficient.

The flight I booked was conveniently timed, had one brief stop and was going to be quick. The flight I ended up getting was delayed, took longer, had a far longer layover and arrived hours later than planned. Thanks for nothing.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Flight was good. However, they had everyone board the plane then made us sit there on the tarmac for an hour plus due to maintenance issues. Besides that flight attendant and pilot were amazing.

Check in agent was helpful and nice. Flight was OK. Our flight in Chicago was delayed 8 hours without an explination. This was our journey home. After a horrible flight experience on on the way to our vacation where our plane was diverted for an emergency medical issue, was grounded for hours, we missed our connecting flight by 25 minutes, and it took a day yo get re-booked, this was yet another bad experience that American seemed unwilling to help out with, much less compensate us for the

Entertainment was very plentiful, staff were courteous. Seating was HORRIBLE. That is the most cramped I’ve ever been on any flight …Jet Blue and Spirit included. Very uncomfortable for a six hour trip.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports