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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$1,063
Santo Domingo
Santo Domingo2 stops$1,163
Nassau
Nassau1 stop$956
Kingston
Kingston2 stops$1,234
Punta Cana
Punta Cana2 stops$1,063
Santo Domingo
Santo Domingo2 stops$1,163
Nassau
Nassau1 stop$956
Kingston
Kingston2 stops$1,234
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 $722, 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 December and August, when the average cost of round-trip tickets is $1,531 and $1,496 respectively.

Good to know

Low season

March
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 20% 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 8701 reviews
8.5Crew
7.8Entertainment
7.2Food
7.8Comfort
8.1Boarding
Airline reviews

Great overall experience and use of the Delta One lounge was amazing!

10.0 ExcellentAvery, Nov 2026
Read more Delta reviews

Great overall experience and use of the Delta One lounge was amazing!

I used by Skymiles to upgrade to First so that I could comfortably work using my laptop. But WiFi was intermittent and unavailable for long periods. I feel like I wasted 70,000 miles :(

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

Loved the easy process to board and the experience overall was smooth

Set on the plane for two hours before pushing off the gate due to the power source issue being fixed which was known before letting people board the plane. On top of that it was very hot as AC was not working properly. Terrible experience and limited communication provided by the crew on the status of the issue. They should let people deplane while issue is addressed instead of frying them and glued to the seats.

I am United’s newest fan. The planes are clean, the staff is so friendly and snacks are more than just old pretzel crumbles. The captain came and said hello! Truly amazing experience

1 person checking us as we boarded, left gate on time, 12.30 we are told we were held for 15 mins as other flights were waiting to take off, captain due to rain … they were having a longer gap between take offs , 3pm we took off , they went land route via New Orleans in to Florida landed at 5.45pm offered coffee and a biscuit

Service was slow Flight was very loud at back of plane

There was no internet on the flight. As an executive flying during prime business hours, having internet is critical for a smooth experience. This impacted productivity and time that will need to be spent later to do the work I could have done on flight.

Terrible boarding - 4 flights boarded from the same gate. Chaos there; long ramps to the plane.

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.

Got to gate late and they made me check my bag but when I got on flight there was lots of overheard bin space .

The gate agent in BNA got irritated with a lady for asking her about standby's and refused to hand out assigned standby tickets to ANYONE until Group 6 . She punished all standby passengers because of the one lady she did not like. When we boarded she said thank you to everyone as we scanned our boarding passes except the lady in front of me. Very petty and unprofessional

The old CRJ700's are rough, slightly larger regional jet would have been nice.

It was unfortunate that the plane had mechanical issues and delayed our flight, but I am glad we made it safely! On the first American flight from Charlotte to Phoenix, they changed the gate without getting a notification, and I had to make a mad dash!

The intuit carrier I have flown with that doesnt have WiFi available on board - at least not on the A380. Meal I wanted wasn't available and the meals I did get were all served cold to warm at best.

The flight was delayed several times as they didn't have pilots. Then we were boarded on the plane and again waited on the tarmac for over 30-40 minutes waiting for pilots to board. The in flight entertainment was confusing at best on how to use it. It took multiple attempts to get wifi to connect and by the time it worked the flight was almost over.

The flight was delayed and gate changed so that was not fun and the flight to Dallas from LAX was very delayed on Sunday. It was just not a great experience due to the delays both ways.

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