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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
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Montego Bay, Jamaica
Montego Bay, Jamaica
13h 04m3 stops
from $763per person
Nassau, The Bahamas
12h 07m2 stops
from $787per person
San Juan, Puerto Rico
12h 34m2 stops
from $815per person
Santiago de los Caballeros, Dominican Republic
11h 58m2 stops
from $981per person
Saint Thomas Island, U.S. Virgin Islands
14h 40m2 stops
from $1,056per person
Simpson Bay, St. Maarten
Simpson Bay, St. Maarten
15h 10m5 stops
from $1,108per person
Willemstad, Curaçao
Willemstad, Curaçao
14h 50m5 stops
from $1,147per person
Providenciales, Turks and Caicos Islands
Providenciales, Turks and Caicos Islands
14h 06m4 stops
from $1,292per 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 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

August
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.

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 13008 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.0Food
7.0Entertainment
Airline reviews

Service is always great with Alaska. Baggage services seems to be delayed in Seattle but Alaska airlines follows up with excellent customer service

10.0 ExcellentChristine, Oct 2026
Read more Alaska Airlines reviews

Service is always great with Alaska. Baggage services seems to be delayed in Seattle but Alaska airlines follows up with excellent customer service

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.

I'm 6' 2" and even in economy plenty of leg room

Flight was very delayed so I was able to get on an earlier flight via stand-by. Crew communicated effectively around delay and worked to make customers comfortable. Wifi was ok, streaming TV was great. App functionality broke down once I was moved to stand-by on earlier flight.

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

Flight delayed over an hour with plane on runway because of weather in an area of the country we were not in or flying to.

Flight was delayed almost an hour because the cleaning crew broke one of the bathroom doors.

Comfortable seats and good crew. There should be some breakfast options in menu for economy class to purchase Wifi was not working in the flight

First class flight crew was barely available. They came through 3 times while we were on the plane for nearly 4 hours.

Please stop those idiotic and unrelenting announcements, commercials and stupid credit card drivel. All together about 15 minutes of stupidness that annoys each passenger.

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

On time. Accommodated carry on and personal bag in the plane. Good entertainment available and access without using own device. Gave a whole can of juice rather than a pour. Seat did not recline 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.

It would be helpful to be able to download an eticket from either American airlines or Cathay Pacific; not just Cathay Pacific.

Flight delayed 6 hours. Would mean I would miss My connections to Glasgow and my reason for going back. AA staff were completely useless in figuring out how to re ok me. My wife 200 miles away was on kayak offering suggestions. Also NO alerts from AA by phone or text about this delay. Just a $12 voucher for compensation. I ended up on BA

It was OK, but it was delayed about an hour, and my luggage didn't arrive till about an hour and a half after the flight

First no airplane at the gate because the previous flight was canceled (and they didn't know?) Then we board and there's a maintenance issue. Then we're told the technician doesnt have the right certification and they need to call another. Then FINALLY we are taxiing. But wait! Flight plans expire after 3 hours and we were not granted permission to take off. So taxi was halted while a new flight plan was filed. Then....no beverage service. Never flying American Airlines again. If they mess up operations this much, how good can their maintenance or training possibly be?

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

Uncomfortable, not managing boarding process and managing people in the way waiting to board at a later time. Terrible delays

Nothing went well. The crew timed out, they sent us to 7 different gates, my original flight got delayed 8.5 hours, and the best American could do was give us a $12 food credit.

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