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Cheap Flights from Anchorage to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$999
Santo Domingo
Santo Domingo2 stops$1,067
Nassau
Nassau2 stops$787
Kingston
Kingston2 stops$1,324
Punta Cana
Punta Cana2 stops$999
Santo Domingo
Santo Domingo2 stops$1,067
Nassau
Nassau2 stops$787
Kingston
Kingston2 stops$1,324
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?

No, with an average price for the route of $711, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Anchorage to Caribbean Islands is September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $1,496 and $1,383 respectively.

Good to know

Low season

August
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 8% increase in price.

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 3 airlines serving from Anchorage to Caribbean Islands

 
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.
7.8
DeltaOverall score based on 8608 reviews
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
7.8Entertainment
Airline reviews

The flight was delayed to board, then delay in landing and extremely bumpy landing.

2.0 MediocreVarun, Sep 2026
Read more Delta reviews

The flight was delayed to board, then delay in landing and extremely bumpy landing.

Late flight, screens not working and still had to pay for a drink

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 attendant incredibly rude. Stuck her finger in my drink and didn’t even have the courtesy to apologize.

I like the first class seat amenities like the phone charger on the armrest even though it didnt really work on mine and the partition between the seats. I also liked that there were additional places to stash things during the flight. The food I got was steak and it was really tough to cut with the knife. Chewy too. A little disappointed in that. I liked that your name is on the screen too. nice touch. great service overall.

Good, our flight was delayed but that was totally out of their control due to weather and a presidential visit.

overall a very good travel experience - left on time, arrived early. Mostly a smooth flight. Polaris seats were excellent, very good service and nice food with options.

The very best airline service I have experienced. Better than domestic airlines first class and I flew Economy Plus!

When we boarded we were treated with care and it never stopped. Got towels before breakfast and after snacks was a lovely touch!

Price was crazy watch it if you Chan he your flight

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.

Legroom was decent, but the seat comfort was horrible; I believe the seat cushions have lost their cushion. I was uncomfortable and had back pain throughout the nearly five-hour flight. WiFi did not work despite my attempts to get it up and running. This was very frustrating as passengers all around me were streaming football games, movies, and accessing email and text messages. One flight attendant suggested it was my seat, but that makes no sense, given WiFi doesn't work that way. On another note, I rarely have a good experience with aainflight.com.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The plane was delayed after we boarded - although they sent an email to my work email (which I did not get until later) there was no announcement from the PA about the delay in flight. Fortunately, they made up the time in the air and we landed around the original time.

I couldn’t get a beverage because my tray table was broken

Comfy and timely flight thanks to Cathay to all crew and the captain for our smooth landing.. above all thank You Lord for our Safe flight ❤️🙌🙏🏽

Flight took additional prep time since plane came from Mexico, which resultrd in boarding and plane prep being delayed for additional cleaning procedures. Once boarded, plane tire was identified as being low on air and needed to be replaced, which creared the need to deboard and further delays for what was already a late night flight. Would have expected a better scheduled turn around and prep buffer that would have not created that degree of delay and deboarding

Very cold on board it was like having 16hours sitting in a fridge

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

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental