$437 Find Cheap Flights from Anchorage to Caribbean - Compare and Save

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Cheap Flights from Anchorage to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
San Juan, Puerto Rico
13h 26m2 stops
from $815per person
Nassau, The Bahamas
18h 49m5 stops
from $887per person
Santo Domingo, Dominican Republic
13h 19m2 stops
from $973per person
Saint Thomas Island, U.S. Virgin Islands
14h 34m3 stops
from $989per person
Kingston, Jamaica
24h 52m4 stops
from $1,315per person
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean flights

Get data-powered insights and trends into flights from Anchorage to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Anchorage to Caribbean?

The cheapest month for flights from Anchorage to Caribbean is April, when tickets cost $947 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $1,284 and $1,275 respectively.

Good to know

Low season

April

Cheapest flight

$437
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Anchorage to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Anchorage to Caribbean?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Anchorage to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Anchorage to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 4 airlines serving from Anchorage to Caribbean

 
Need help choosing which airline to fly with from Anchorage to Caribbean? 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.
7.9
Alaska AirlinesOverall score based on 12940 reviews
7.0Food
7.8Comfort
8.5Crew
7.0Entertainment
8.1Boarding
Airline reviews

Everything was great. Due to an accident on the Glen Hwy attendants could not make it to the airport. A delay while new crew was located

10.0 ExcellentJodee, Jul 2026
Read more Alaska Airlines reviews

Everything was great. Due to an accident on the Glen Hwy attendants could not make it to the airport. A delay while new crew was located

My experience with Alaska Airlines was great! Crew are always friendly and attentive. Alaska Airlines goes out of their way to make guest feel appreciated.

Completely full flight. Boarding was smooth, but people didn’t listen about use of overhead bins which is typical. We pre-purchased a snack which was tasty. Drinks were good and plentiful. Flight left late because previous flight was delayed.

Ok, but nothing special. Long flight with no blanket/pillow set.

The tray wasn’t cleaned, it had crumbs from the last flight Other than that it was very comfortable by

Kayak wouldn’t refund me for a flight I was trying to cancel through Kayak. Alaska airlines said I had to cancel through Kayak. I called the customer service line and they couldn’t refund the flight that I booked through Kayak either. You stole my money. You will be hearing from my lawyer.

Service was great! 👍 Seats were small and absolutely not enough leg and feet room!!!

Flight was delayed several times then eventually cancelled which caused issues with our hotel, car rental and tickets to planned event. We also spent unplanned expense with Lyft to and from the airport which was frustrating. Customer care was not present during whole time at the airport.

We received a check-in reminder the day before the flight, and it listed the flight at a later time. Correct flight number, same seats, etc. for 3 hours later. I called the airline to confirm and they had no record of the email. The info was wrong, and we would have missed our flight if we'd assumed it was correct. I want to know where/how we received this incorrect info.

My experience would’ve been great because we were on a new plane, but they said as we boarded that the plane would be too new to have WiFi, which to me is unreasonable - newer planes should def have WiFi! It was a 5 hour flight from Anchorage to San Fran and because there was no WiFi, I had to take an unexpected half day off work, which was super annoying because I had a lot to do and we only found out a few minutes before takeoff.

It’s a 3 hour flight with no entertainment and no WiFi due to Delta using old planes on this route and food is cold. Today we were told no potable water on the flight to even make coffee or tea. Ridiculous service in this direct route for business travelers and non business travelers

The crew was excellent but the entertainment did not work. The 3mm jack for the headphones was faulty and no sound was available for entertainment.

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

Plane congestion resulted in a 1 hr wait from landing to arrival at the gate. This was in addition to also experiencing extreme delays on my incoming flight.

Delayed too much. 1.5 hrs in the airport and another 1 hr in the runway. Got too late in the night. There was no proper food available.

awesome team work seen since on board till off plane in my destination. thanks you so much.

Job well done, being treated for good and helping a lot . thanks you so much till will meet against.

Very disappointing that on an international business class flight they would not give me access to the lounge in Boston. They said it was because it was a codeshare flight. International business class should include lounge access regardless of codeshare.

They did not have free WIFI and I was not okay with that!

Food was very bad Crew was not so welcoming. Chairs was so uncomfortable

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.

Confusion at boarding with my seat (there wasn't one) that I had to have corrected using my status; then because of that had to check bags. And then a very long delay on the tarmac with no air conditioning on a very warm day. It was just a miserable experience all around.

Flight was delayed which isn’t the airline’s fault, but the communication around it was terrible. I left the lounge to show up at the gate to board at the time in my app, and the flight in front of mine was still boarding and the inbound plane hadn’t even taken off yet. Delays were slow to show up in my app. Improved communication could have let me have a more pleasant experience in the lounge vs waiting 1.5 hours at the gate.

We had to de-board do to maintenance and there was ZERO help with getting rebooked. The flight was delayed by over 24 hours. Quite ridiculous. When I. called Kayak to get help to rebook, they said they couldn't and that it had to be done at the American counter that didn't exist without going outside TSA security, which I did.

I spent 12 hrs getting home and had a direct flight that should have taken no more than 3 hrs. The first plane has an issue, was on the plane for over an hour before we had to deplane and move from A19 to A39 to board another plane. Boarded that plane to wait for another 45 minutes for it to also have an issue where we had to deboard. After everyone had went to get something to eat the food vouchers came out and half of us could not use. We then had to wait until 8:00 pm to board and finally got to Columbus Ohio at midnight. We were told that our luggage was on baggage 5. I waited 30 minutes to then realize my luggage was on 4. No notification sent. Horrible communication and I have a priority status.

My flight depature was changed. Then it was delayed, and then cancelled after I reached the gate.I paid $231 for a hotel room that I didn't get to use because I arrived 24 hours later than I was suppossed to. My wife had to pick me up from the airport and I had to pay for an another ride back to the airport the next day. They did get me faster/ priority through TSA. The 2nd flight was okay

Had to pay for WiFi, delayed start, and sat on the runway forever.

As with most flights these days it was delayed by about 30 min.

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

Complete your trip to Caribbean with a hotel stay or car rental