$446 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 Cana2 stops$1,003
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$762
Kingston
Kingston3 stops$1,143
Punta Cana
Punta Cana2 stops$1,003
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$762
Kingston
Kingston3 stops$1,143
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 $683, 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 July and December, when the average cost of round-trip tickets is $1,375 and $1,338 respectively.

Good to know

Low season

April

Cheapest flight

$446
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 22% lower on average.
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 8513 reviews
7.8Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

Delta is a perfect partner, offering the gold standard across the board.

10.0 ExcellentDavid, Aug 2026
Read more Delta reviews

Delta is a perfect partner, offering the gold standard across the board.

Our flight from Detroit to LaGuardia on Thursday 8/20 was delayed from 555 to 910 due to storms and a ground stop at LGA. It’s never fun to be stuck at the airport but I thought the desk crew and captain handled it well and kept us informed. I especially liked how they referred to us as their “LaGuardia family.” I am a loyal delta customer and this is one of the reasons why.

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

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

Polaris seat is plush and conducive to sleep. Cabin crew was experienced, highly attentive and helpful when any need arose, such as finding a lost phone in the seat mechanism. Food was a disappointment, especially the Japanese items coming out of Newark all seemed a bit overcooked, though the empanada snacks served midway were a hit.

The flight was excellent. Their was no service as we boarded, the flight attendants spent about 30 minutes just taking and not really caring that the cabin was about 80 degrees and did not offered any beverage to first class passengers or any passenger. The flight from DEN to ONT is not long but not under an hour, we received one drink and bag of chips if you were lucky. I was in first class…. I did leave my hat on the plane and it only took less than five minutes for a United rep to locate and bring it to me.

Flight did not have wifi service. It was experiencing technical difficulties. Definitely and old plane that needs updating.

Very Poor. Significant delays getting to Chicago and then very poor communication on delays in Chicago to Cleveland. We could have rented a car and driven there faster than the delays ended up being.

A little more friendliness from that crew of the day.

The app logs you out right when you are boarding requiring all passwords and reservation number for the flight. Super annoying

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.

Nothing with the flight. It was good. Crew as very helpful especially fist class flight attendant.

I am generally an American Airlines loyalist but this flight was not good. I was seated in an aisle seat and the gentleman in front of my had his seat fully reclined which made it impossible to work on my laptop, eat or drink.. The gentleman in the middle seat was watching something on his phone without headphones.

Wheelchair folks are great. Food not to my liking. Crew more interested in their lives than the passengers. Got the job done but just the minimum.

Flight was smooth and on time: however, this flight was filled with advertising. We got it over the speaker system both when we took off and when we landed. Flight attendants were handing out sales flyers when we landed. It was not a good look.

More space for economy, and the bathroom size is only for people with size XS

We were delayed in CLT for 4 hours for mechanical issues resulting in us not leaving till 1:30AM and landing at 2:30 AM, so getting home at 4AM. The crew at the desk had no answers and provided very little information. I received a food voucher via email/app however there were no food places open. Even the walk up and scan your own places did not accept the QR code. I know mechanical issues occur but better communication would have made an unfortunate situation less frustrating.

The first leg of my trip from Dallas to CLT was smooth from check-in to landing. The snack, biscott cookie really needs an upgrade. Even if the upgrade is a choice of the cookie or pretzels.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports