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$973
Nassau
Nassau1 stop$785
Kingston
Kingston2 stops$1,324
Punta Cana
Punta Cana1 stop$999
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau1 stop$785
Kingston
Kingston2 stops$1,324

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 $718, 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 $1,419 respectively.

Good to know

Low season

March
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 8636 reviews
7.2Food
7.8Entertainment
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

Gate agent and flight attendants were efficient, but more stern than warm.

8.0 ExcellentConor, Oct 2026
Read more Delta reviews

Gate agent and flight attendants were efficient, but more stern than warm.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

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

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

Old plane, no amenities. Very abrupt landing. Unnecessarily long taxi time.

The flight was for my mom in wheelchair the staff in Newark wer not friendly took a long time to even get a wheelchair she almost missed her flight because they finally got a chair few minutes before boarding they had to rush her to the gate. They took her carryon and checked it as a bag told her don’t worry free of charge but they charge the credit card anyway. She also told me the seats are not comfortable at all as if they were broken she could feel the bars in the seat SFO staff was much better overall she had the worst experience

Wifi is very frustrating - could not connect and therefore unable to work on the trip

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

Premium economy was worth it. Great seats and good food.

Food was good. Clean aircraft. But why do the airlines make the seats so narrow?! Your executives should have ride in a seat so restrictive for 11 hours and see how miserable it is! When.we got to MUC they changed my boarding gate 3 times for my next 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.

I always looks forward to the Biscoff cookies and they weren’t offered….

I had to buy another ticket and you haven't reimburse me for it.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Had to find alternative flights because of AA lateness and bad planning

Fliy was late missed my connection ,. I had to find altery transportation.

When we landed, there was only one gate agent to handle three planes, including retrieval of carry on luggage. I was stuck in the jet way waiting on my carry on for almost 20-30 minutes. NOT GOOD

The flight was overbooked. And the gate agent basically said that the flight will not leave unless two people came forward to give up their seats. Offered money. Raised the $$ too. But we were there for a while and flight was delayed. When passengers approached the gate agent asking what would happen if no one volunteered- the answer was flight would be cancelled! Ridiculous! It’s American’s fault for overbooking. The service level is going from Bad to worse it seems.

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