$430 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 Cana1 stop$999
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$767
Kingston
Kingston2 stops$1,269
Punta Cana
Punta Cana1 stop$999
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$767
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 $730, 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 $1,386 respectively.

Good to know

Low season

April

Cheapest flight

$430
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 10% 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 8545 reviews
7.2Food
8.1Boarding
7.8Comfort
7.8Entertainment
8.5Crew
Airline reviews

Very aggressive at the boarding area of only allowing one person passed a line/ sign

10.0 ExcellentHugh, Sep 2026
Read more Delta reviews

Very aggressive at the boarding area of only allowing one person passed a line/ sign

Everything was very good or excellent, but the seats were extremely uncomfortable and painful.

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

Airplane is not very clean, food quality and taste was not good. Lufthansa used to be good but nowadays went down. Overall experience is just okay, wouldn't fly again, prefer Turkish airlines.

I missed the flight due to maintenance issues. This is the second flight I’ve missed in four days because United allows such little time between layovers. Very disappointing

My return flight to Honolulu (UA 1170) was on a 777-200. I’d forgotten the weird seating arrangement in first-class (2-2-2); I was in 1B, so I faced the passenger in 1C. Unfortunately, there was a problem with the flight computer, so we left LA an hour late (6:05pm). The meal I chose was Korean BBQ Glazed short rib. It was served with a nice salad and fried rice. This meal was better than breakfast on the outgoing leg. All in all, a decent flying experience. Ratings: 777: 3.75, food: 3.5, service: 5 (out of 5).

Food was not Good Nuts came very wet & not tasting Good Main course I asked for Steak they got me Chicken because they don’t have more !!!!

It cancelled and we were unable to catch our connecting international flights.

Flight delayed and then cancelled (due to mechanical issues + weather). Poor communication. No one there to help with rebooking and accommodations for the night we had to stay in Newark. Our luggage was taken off the original flight and apparently left on the tarmac in the rain. Items were soaking rain. The following day, the flight was also delayed due to mechanical issues. The second year in a row that I had to sleep in an airport flying from Tokyo to Newark due to mechanical issues compounded by bad weather. Partly bad luck and partly just poor service.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

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 have yet to come across an AA agent or flight attendant that is friendly. They really inhibit a good experience.

if it's a mobile only entertainment experience, please provide a place to hold the device in the back of the seat.

The flight up was great no issues. The flight back home was a cluster. I was told the plane I was waiting on was giving to another flight which caused me to miss my connection flight. Granted the airline did great with getting hotel and vouchr for food.

Flight was delayed and so much of inconvenience related to the gate change.

My original flight kept getting postponed multiple times, I would have missed my international flight if I waited. It was postponed through the next day. I ended up having to drive 3 hours away to get my next flight.

Nothing was good about this flight. Although the flight actually departed more than 3 hours late, due to “air traffic control management” we pushed back from gate 2 hours and 20 minutes late and proceeded to sit 100 yards from gate for and then n tarmac for another 1/2 hour additional 20 minutes

Our flight was delayed to Louisville. What made this worse was they did not have another flight attendant to service the flight. This caused an even longer delay. Then when a flight attendant did show up, she chose to "swap" flights with another flight attendant. Therefore, we had to wait longer for the other flight attendant to come to our flight. This is information that the gate attendant should not have shared. Processes and execution at American are broken. Passengers are feeling it. Fixing this starts at the top of the organization.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports