$430 Find Cheap Flights from Anchorage to Caribbean Islands - Compare and Save

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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 Cana1 stop$999
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$727
Kingston
Kingston2 stops$1,269
Punta Cana
Punta Cana1 stop$999
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$727
Kingston
Kingston2 stops$1,269
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 $744, 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

April

Cheapest flight

$430
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 5% 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 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 8573 reviews
7.8Entertainment
8.1Boarding
8.5Crew
7.8Comfort
7.2Food
Airline reviews

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

4.0 OkayAlexander, Sep 2026
Read more Delta reviews

Both legs on the way were smaller planes, each had a mechanical issue causing a delay

Delta exceeded my expectations! I am beyond satisfied. Thank you!

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

Crew was great. Seats are cramped and uncomfortable and I’m a small person.

Awful. Delay after delay. And then again on the tarmac.

WiFi was slow as compared to trip down. Maybe because it was a night flight and more people were using it?

Excellent except for the 2 screaming kids who wouldn’t stop crying and screaming for the entire flight but what are you going to do? The flight was early- good experience

Kept changing the takeoff time and the moved it up so arrived when boarding had already started. Then sat waiting to taxi in for a long time

It was partially ok .. not anything like from Orlando to Houston... first the flight attendant was not so nice and insisted on have a small backpack down when really was not to put in danger anyone, also the beverages they were not so good... not big chance to select other tea.. the seat was partially ok could not have those flips to hold your head.. and finally when it land off in Guadalajara, it was raining and the flight was going to the main area then go back and drop us out of nowhere with the rain.

Airplane is not very clean, food quality and taste was not good. Lufthansa used to be good but nowadays went down. Overall experience is just okay, wouldn't fly again, prefer Turkish airlines.

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.

My flights were all delayed , mostly due to technical issues with AA aircrafts. I had to rebook my trip 4 times . I lost my whole day and finally arrived in LAX around midnight. This was a very bad experience with American airlines , I will always try to avoid flying with them

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

Delayed and WIFI was not working for most of flight.

The big challenge here was that the inbound flight was delayed, THEN, the aircraft was deemed in need of service, so we had to deplane after being a few minutes away from departure, THEN we had to switch terminals, where another plane in our gate had maintenance issues so we had to change gates again. I am a regular flyer (not on American) so I understand these things happen. The crew was great. The pilot in particular was gracious and understanding and stayed with the passengers the whole time to answer questions and give updates - that was impressive. But the flight was massively delayed as a result, and today I really wanted to be home in time. Sigh The flight was otherwise great.

I am Plstinum Pro snd was standby on earlier flight. They gave seats to people that asked rather than follow standby order. When realized what was happening was too late to get on as no seats left. My scheduled flight was late. Then filled the seat beside me Ruth rude person that they had to move from her original seat

My flight was delayed close to 10 times over the course of the evening. I was originally scheduled to depart at 7:03 PM but did not leave until 12:33 AM, resulting in over 9 hours spent waiting at the airport. The only explanation provided was that the aircraft kept being swapped, with no clear reasoning as to why. Weather conditions at both DCA and Tampa were clear, so that was not a factor. The only accommodation offered was a $12 food voucher, which was entirely insufficient given the length of the delay. Overall, I was completely unsatisfied with this experience. A delay of this magnitude with no meaningful communication or accommodations is unacceptable, and I would have expected much more from American Airlines in terms of customer care.

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

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