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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$1,069
Santo Domingo
Santo Domingo2 stops$1,013
Nassau
Nassau2 stops$956
Kingston
Kingston2 stops$1,326
Punta Cana
Punta Cana1 stop$1,069
Santo Domingo
Santo Domingo2 stops$1,013
Nassau
Nassau2 stops$956
Kingston
Kingston2 stops$1,326
Booking Insights

Price, demand and travel trends for Anchorage to Caribbean Islands flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

Are flights from Anchorage to Caribbean Islands cheaper or more expensive than last year?

Fares from Anchorage to Caribbean Islands are about 17% lower than they were in November last year, averaging $1,023 round-trip.

What's the cheapest month to fly from Anchorage to Caribbean Islands?

November is typically the cheapest month to fly from Anchorage to Caribbean Islands, with round-trip fares averaging $1,069. August and December are usually the most expensive, averaging $1,496 and $1,275, respectively.

How do fares from Anchorage to Caribbean Islands vary by day of the week?

On average, Tuesday is the cheapest day to fly from Anchorage to Caribbean Islands and Sunday is the most expensive. Looking at the past 12 months of KAYAK data, it's 7% more expensive to fly on a Sunday compared to Tuesday.

What's the best time of day to fly from Anchorage to Caribbean Islands?

It's cheapest to fly to Caribbean Islands in the morning with average prices of $1,025. The night is the most expensive time to fly, with average prices of $1,246.

Key details for Anchorage to Caribbean Islands flights

Low season

August
Beat the crowds with an average 54% drop in travelers.
The most popular month to fly with an average 79% increase in travelers.

Your Anchorage to Caribbean Islands flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • How much should I budget for a flight from Anchorage to Caribbean Islands?

    Over the past 12 months, round-trip fares from Anchorage to Caribbean Islands have typically cost between $1,066 and $1,360.

  • Which airlines fly nonstop from Anchorage to Caribbean Islands?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Anchorage to Caribbean Islands. One-stop options include:

    • United Airlines
    • Delta
    • American Airlines

  • Which cabin classes are available from Anchorage to Caribbean Islands?

    On flights from Anchorage to Caribbean Islands you can book Economy Class or First Class.

  • What are some popular landmarks around Caribbean Islands?

    Caribbean Islands is home to many popular sights. KAYAK travelers' favorites include:

    • Viejo San Juan
    • Palm Beach
    • Eagle Beach
    • Puerto Rico Convention Center

Your guide to booking Anchorage to Caribbean Islands flights

Get tips on when to book, when to fly and what to know before your trip.
  • Flexible with your dates? Fly in November to save some money. It's typically the cheapest month on this route, while flights in August will cost you the most.
  • Fly out on a Tuesday to get the cheapest fares. Avoid Sunday flights, which are about 7% more expensive.
  • Start your trip in Punta Cana, the most popular destination in Caribbean Islands. From there, it's easy to continue on to other popular spots such as San Juan, Oranjestad and Nassau.

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 8719 reviews
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
7.2Food
Airline reviews

The app could have worked in any way to enable re booking, which I did by downloading 2 other apps and ignoring Kayak.

2.0 MediocreChristian, Nov 2026
Read more Delta reviews

The app could have worked in any way to enable re booking, which I did by downloading 2 other apps and ignoring Kayak.

flight was hot, it was delayed and there was no wifi.

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

We had missed our scheduled connecting flight to Casper and was on the late arrival of 10:15. The plane pulled up to the gangway and nobody was getting off after waiting several minutes. The pilot made an announcement that he needed to start the engines and make a circle back to the parking spot 6 inches closer. Overall, it took 45 minutes to get off the plane that usually takes less than 15. Because of the flight delays out of Casper at the beginning of our trip and on the way home, we booked our next trip out of Denver which is a four hour drive each way.

Flight delay for something to do with an accident on a runway. Our connection time was scheduled for 1 hour and 11 minutes which wasn’t enough with the departure time. We eventually got to our home airport 3 hours late.

The plane to Casper is of the two by two variety which has small bag only overhead. So many passengers try to put oversized bags overhead and causes delays for the flight. Hand checked bags for all with anything larger than a purse or briefcase would make boarding easier.

Our trip from MSP to DEN was 15 minutes early arriving and made us feel a little better while walking from B19 to B94. We checked the Departure board midway to make sure the gate was still assigned to our flight. Just before we arrived, we checked the board and now it said B62 which was back up a stairway and around a long corner. We were exhausted!

Deplorable not to have WiFi on 5 hr cross country flight and spend thousands of dollars

We left nearly 3 hours late...so that was not a good experience. We boarded and then ended up about 1 hour stuck at the gate. Not a good experience.

It is completely insane to me that first class does not include WiFi. Also does not include lounge access. Port for phone charging did not work. The crew was absolutely lovely, and the food was excellent.

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.

Flight was comfortable- just had to endure a 1 hr delay because of some maintenance issue. Happy that American Airlines does these final checks but just wish they would conduct this maintenance before the flights.

All good. Flight crew was super friendly at the end of a long day

All good. Easy check in and boarding. Lovely flight crew

Friendly crew and pilot. And thank you to the pilot for his smooth landing technique where the wheels don't hit the ground hard - that should be table stakes but doesn't seem to be the case nowadays.

Four hour delay due to late plane arrival- second year in a row on MCO - DCA route. Pitiful service reliability from American. Will avoid in future

Flight was fine, food could have improved (Chicken Enchiladas) and so could the entertainment options on the seat rest (there was none).

I have generally had positive experiences with American Airlines (outside a handful of delayed flights), which is why I wanted to share this feedback constructively. On my recent flight, my travel experience was extremely uncomfortable because my seat mate significantly encroached into my assigned seat space for the duration of the flight. As a result, I was forced to sit partially sideways, with much of my shoulder and upper body extending into the aisle. Unfortunately, my back still hurts from maintaining that awkward position.I recognize that this is a sensitive and challenging issue for airlines and cabin crews to address. Everyone deserves to travel with dignity and respect, and I understand that individual circumstances can vary. However, fairness also requires that all passengers have reasonable access to the seat space they have paid for. When one passenger's use of space substantially impacts another passenger's ability to sit safely and comfortably, there should be a practical solution available.I appreciate the complexities involved, but I hope American Airlines will continue exploring ways to ensure that all passengers can travel comfortably and equitably. This experience detracted significantly from what should have been a routine 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