$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
Montego Bay, Jamaica
12h 45m2 stops
from $763per person
Nassau, The Bahamas
10h 54m2 stops
from $787per person
San Juan, Puerto Rico
13h 18m2 stops
from $815per person
Simpson Bay, St. Maarten
21h 26m5 stops
from $838per person
Santo Domingo, Dominican Republic
13h 19m2 stops
from $973per person
Saint Thomas Island, U.S. Virgin Islands
13h 01m3 stops
from $1,056per person
Bridgetown, Barbados
21h 37m6 stops
from $1,162per person
Providenciales, Turks and Caicos Islands
14h 06m4 stops
from $1,286per person
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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 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 $1,284 and $1,275 respectively.

Good to know

Low season

March

Cheapest flight

$437
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 8% 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 12956 reviews
7.0Entertainment
8.1Boarding
8.5Crew
7.0Food
7.8Comfort
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.

Gate agents call groups one and two and give about 3-5 minutes for each group to board, then the call groups three and four together and it causes a bottleneck in the line. Give each group 3-5 minutes to board before calling the next group.

We sat at the gate for over 30 minutes, with no indication as to why

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

Smooth flight, easy boarding process. Made up time in the air with initial delay due to weather pass through

Flight was over two hours late, but they notified us early in the morning. They ended up changing planes the food on board that was extremely mediocre and we were in premier class.

Usual wait for over a half hour for a gate at Ohare. They tell you you'll get there early then sit on the plane and wait almost an hour

I enjoyed it, again I believe air Canada has better seating options and better drink options

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.

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 don’t think I’ve ever had a flight with American that has been without problems. Mostly delays - this time for over 3 hours. They should have just brought another plane into the terminal but they just had everyone sitting around misterable all day. They turned a 3 hour flight into a 12 hour trip for me (including the “planned” layover). It was ridiculous.

The flight from American side was good, my main issue this was a part of a partner flight with gol, preventing me to use digital boarding passes and doing checking previous of the arrival to the airport.

Id like for them to not have lost my bag. And maybe be a little nicer to me, given the fact they lost my bag.

The flight was delayed but we were given no updates. The time just kept changing in the board. We were delayed on the runway as well. Then, my bag was lost and still hasn't been returned.

The flight landed in Phoenix and taxied the runway for 15 additional minutes. I had a connecting flight I barely made it to because of the delay of the plane taxing the runway.

The flight was delayed a dozen times and finally took off 3 hours late. American gave us 12 dollar vouchers which barely buys you a water at the airport. Options to rebook were easy to access and complete although I didn't go this route.

I have executive platinum status with American Airlines. It seems impossible to be upgraded anymore and I’m never offered a cheese plate or thanked for my loyalty.

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