$427 Find Cheap Flights from Anchorage to Caribbean Islands - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 21% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

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$999
Santo Domingo
Santo Domingo2 stops$1,061
Nassau
Nassau1 stop$794
Kingston
Kingston2 stops$1,269
Punta Cana
Punta Cana2 stops$999
Santo Domingo
Santo Domingo2 stops$1,061
Nassau
Nassau1 stop$794
Kingston
Kingston2 stops$1,269
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 $744, 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 $1,383 respectively.

Good to know

Low season

April

Cheapest flight

$427
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly with an average 8% increase in price.
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 8567 reviews
7.2Food
7.8Comfort
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

I’m on this flight every other week. Same flight, same day of the week, same time of day… Multiple times there are issues getting flight plan registered and FAA approved r to take off. PAPERWORK This is exhausting and it sucks.

2.0 MediocreJames, Sep 2026
Read more Delta reviews

I’m on this flight every other week. Same flight, same day of the week, same time of day… Multiple times there are issues getting flight plan registered and FAA approved r to take off. PAPERWORK This is exhausting and it sucks.

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

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

Awful!!!. I do not recommend United. The flight staff are unhappy and don't attempt to make the passengers feel comfortable or welcome. The food is not edible, and the seats are miserable. My expensive luggage was destroyed, and the ticket prices are too much for the experience.

Even though the incoming flight was delayed by 20 minutes they managed to get us to SFO 15 minutes early.

The business class had to wait to board last. Unacceptable

The air hostess was excellent. I have taken so many flight domestic and international, this is the first time the air hostess was so caring. She was a delight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

It was fine for the most part. But the volume on the announcements was way too loud, and the cabin temperature was chilly. We had the hardest landing I've ever experienced- I think it hurt my back, and the tires squealed when we touched down.

Great, except the canon was so cold. Even the flight attendants put jackets on

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.

The flight was delayed and was not forthright on the time that it was likely to depart where Flight Radar 24 was reflecting a later time that ended up being accurate for the takeoff. The plane was filthy with food smashed into the carpet and crumbs were piled under the seat where I was to put my backpack. It looked like a full sized Lotus Biscoff cookie was pulverized under the seats in my section. The seats were so uncomfortable especially when the person in front reclined his seat completely to where it was smashed against my knees and I am only 5'2". The fruit and cheese box for $13 was lackluster with no flavor and not satiating at all. The plus side is that I did get one full can of ginger ale. The flight attendants looked miserable and tired, probably due to the last minute need for a new flight attendant to fill in since the original one assigned could not continue on to service this flight. Improve the flight experience for customers and maybe the irritability and stress of flying in today's environment will not negatively impact the joy and stress of the employees/flight crew. This is why I prefer to fly non-US carriers whenever given the chance.

I believe my father had a good flight. What was not good, was the associate who helped us during Step 2 of check-in. After getting his boarding passes and bag tags, we proceeded to Step 2 where we were met with Carol. This was around 3:15-20pm at Phoenix Sky Harbor. She weighed my father’s checked bag which was 2lbs over, she recommended removing a pair of jeans to correct this. My father asked/joked if “she could just let him go” and she fairly rudely responded something along the lines of, “I don’t own the airline so no I can’t do that”. From this point on I just want to assume she was having a bad day. I spent my life raised in a business and front-facing customer service so I understand previous clients can make you feel irritated. How she continued to act leads me to believe she was really careless about her job or racially biased/straight-up racist. After we moved the 2lbs to his other bag, she told us she believed he would need to claim his bag at his connecting flight in Hong Kong, before it could go to his final destination, Malaysia. This thoroughly confused us as we are fairly frequent international travelers and 95% of the time the bag is sent to its final destination without this requirement. Last time we traveled to Malaysia was less than a month ago, so again we’re fairly confused. Multiple times she used a fairly aggressive tone of “I know what YOU THINK, this is what I believe”. The multiple “YOU THINK” as if we didn’t understand what she was saying was rude and insulting, and her tone came along with a insincere smile, hence the feeling of she was racially biased. Despite the fact that she might have been having a bad day previously, it is AA’s airline’s duty to train their employee about international bag protocol, as clearly AA is a major partner of internationally traveling airlines. Carol made the experience overall unenjoyable sending my father off and made us both question AA’s training of their employees.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

Sat on tarmac at arrival at DFw for more than 30 min waiting for a gate.

Old dirty plane but great lie flat seats in business class

Business Class layout was excellent. The seats were not nearly as comfortable as UA, Delta or Air New Zealand (the best). Nor were the controls as flexible. Food was okay but not great. Breakfast pancakes were like cardboard.

Communication not good, too many changes. Three flights were cancelled due to weather and the options were not acceptable. I had to cancel my Canada portion of the trip.

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