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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$1,039
Santo Domingo
Santo Domingo2 stops$1,058
Nassau
Nassau2 stops$767
Kingston
Kingston2 stops$1,214
Punta Cana
Punta Cana2 stops$1,039
Santo Domingo
Santo Domingo2 stops$1,058
Nassau
Nassau2 stops$767
Kingston
Kingston2 stops$1,214
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 $1,419 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 14% 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 8654 reviews
7.2Food
8.5Crew
7.8Entertainment
8.1Boarding
7.8Comfort
Airline reviews

WiFi only works on about 75% of my Delta flights. I rarely fly SW, but their WiFi works 100% of the time and is easy to connect. On my DL flight from DCA to BNA today, I try to connect to WiFi for about 30 minutes, but I gave up. I have a lot of work to do, and I lost two hours today. Very frustrating.

6.0 GoodBenjamin, Oct 2026
Read more Delta reviews

WiFi only works on about 75% of my Delta flights. I rarely fly SW, but their WiFi works 100% of the time and is easy to connect. On my DL flight from DCA to BNA today, I try to connect to WiFi for about 30 minutes, but I gave up. I have a lot of work to do, and I lost two hours today. Very frustrating.

Only flew a short distance from Buffalo to New York City JFK SO it was okay

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

Everything was OK except the meals, that was overpriced chicken meat.

Seat would not recline, and charger did not work. Person in front of me reclined before we took off and left it reclined when they got off the plane. Nobody ever told them to put their seat in upright position....which meant I was somewhat trapped in my window seat when deplaning. Another passenger had to go to their seat and un-recline so I could get out.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

Not so good. Crew was not as attentive as they should have been especially if flying business class. Only offered dinner 2 hours after takeoff. My flight attendant seemed overwhelmed. Pushed my help button but no one came. I explained everything on my previous review.

My flight from Boston to SFO was fine. Crew was friendly and helpful. Food was mediocre. Fright from SFO to MNL was not as good. My flight attendant was friendly but didn’t seem to have a lot of experience. She seemed overwhelmed. Also, this was the only red eye business class flight I’ve flown which only served dinner 2 hours after takeoff in a 13 hr flight. When I woke up 1 hr before landing, everyone was eating so I assumed bkft was being served. I pushed my button for help and no one came so I approached my flight attendant and she said they don’t serve bkft but she gave me choices for lunch or dinner. I routinely fly business class but I was disappointed with the lack of service and attention I was given on this flight. Also, most airlines will offer a snack or coffee before bkft is served but this was not offered during this flight. Overall, it was disappointing.

The first leg of my trip the Republic Airlines aircraft was late due to a maintenance problem. Then I called United to reroute. Their reroute airline lost my bag but found it and returned it two days later. Hopefully my return trip home is better.

There was not even a single time where united airlines from lga has made to the gate straight , 1 hr if delay today

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.

Good flight, excellent personnel; poor comfort, small seats, big cost.

No flight delays. No need to rebook to make connections. Enjoyed second leg of flight on Iberia.

Very Good in general. Serving attitude are very good. Just a suggestion: There 2 things can be improved: 1. The flight attendants can lower the voices when they talked in the serving station. Sometimes they talked loud and we could hear clearly what they said about the passengers. 2. Please don’t throw the utensils and plates it’s too loud and noisy. They broke the glasses and plates sometimes at the business class. These all could be done in a gentle way. Just some small observations. Thanks.

Flight was delayed a couple of times. Which is annoying, but manageable.

Too little snack and drink for almost 6:00 hr flight. Should have serve some food.

At 5:46 am EST, when I arrived at my departing gate, your gqte agent told me that I could not board the flight because the flight is closed 15 minuets before departure. However, the same gate agent escorted a woman (standing right next to me) at the gate onto the flight which, proves that I could have boarded the flight just like the woman I watched board the flight. The gate agent stated "she was here before you". 1-why was she not already on the flight & 2-how and why was she able to board a "closed" flight that I was not. Additionally, although 6am EST was the time of departure, the plane did not 'pullback' from the gate until 6:15am EST The same gate agent told me that the "boarding closes 15 before departure time" is printed on my boarding pass. This statement is not displayed on my digital boarding pass that I downloaded from AA.com. She also told me that this in stated on AA.com whent I booked my ticket however, since am travelling for work, I booked my flight thru my firm's (Deloitte Consulting) corporate travel app, not AA.com. Marc W Brown

What an amazing plane! We flew a 787 to Miami. Although the Internet was not functioning, it was a wonderful flight.

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