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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$1,059
Santo Domingo
Santo Domingo2 stops$1,013
Nassau
Nassau2 stops$818
Saint Thomas Island
Saint Thomas Island2 stops$1,116
Kingston
Kingston2 stops$1,234
Punta Cana
Punta Cana1 stop$1,059
Santo Domingo
Santo Domingo2 stops$1,013
Nassau
Nassau2 stops$818
Saint Thomas Island
Saint Thomas Island2 stops$1,116
Kingston
Kingston2 stops$1,234
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 $716, 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 December and August, when the average cost of round-trip tickets is $1,531 and $1,496 respectively.

Good to know

Low season

March
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 20% increase in price.

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 8692 reviews
7.8Entertainment
8.1Boarding
7.2Food
7.8Comfort
8.5Crew
Airline reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

4.0 OkayRonald, Oct 2026
Read more Delta reviews

We experienced delays in small increments that added up to more than an hour. At the gate, staff showed little concern and compared our delay with the inbound flight’s two-hour tarmac wait, which didn’t address our situation. Once onboard, the flight attendants seemed tired and unfriendly. I understand delays are frustrating for everyone, but passengers shouldn’t feel blamed for them. During the flight, a bright light above the emergency exit stayed on. It was concerning, and no one explained it or offered passengers the option to move. After landing, we waited about 30 minutes on the tarmac for a gate, then waited again for an agent to connect the plane to the terminal. From the Reagan gate staff to the cabin crew and RDU personnel, the service felt dismissive throughout. Overall, this was a stressful trip and a very disappointing customer-service experience

My flight from Atlanta to Oklahoma City was delayed multiple times. I ended up arriving in Oklahoma City nearly two hours later at around 1:50 am the following morning. This was a highly disappointing experience.

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

I need to note that this flight experience was generally fine but the boarding situation was absolutely a mess and there wasn’t any actual priority boarding. I rated the experience poorly because I’m am genuinely so frustrated with the crew on United taking the baggage space in first class. This flight it didn’t happen, but the last few flights (when I ironically don’t get an opportunity to provide feedback) have been spoiled because upon entering the first class cabin as one of the first few seated passengers, the overhead bins are full and ‘crew’’ tags are on the bags of those taking space. I don’t intend to infer some sort of a class or caste system but it’s absolutely ridiculous that the crew takes the overhead storage above and beyond their most loyal and lucrative customers. They should not even have economy space IMO. And I’ve gotten grief when I’ve noted to the crew the ridiculousness of the notion that the crew (who are the last off the plane) should have priority over flyers who pay. I hope you find a way to convey this message to United because it’s happening with increasing frequency and I intend to find a way to expose the specific crew members who are doing this on a flight by flight basis. (And I have a day job)

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

Flight and crew were great. Need more legroom and do not allow seats to recline.

Bathrooms broken, Wifi not working, Direct TV stuck in a United credit card loop for whole flight

We arrived to Chicago nearly 30 minutes early, which was great, but then was on the ground for over an hour because the gate was not available. The issue I had was the pilot estimation was frustrating. First he said he was informed it would be 20 minutes but he said "it will probably be more like 10 minutes". After 30 minutes he came back on the comm and said it would be another 10 minutes, maybe 20. I understand he was only giving estimates but he also layered in his own gut feel. We were never told why we didn't have a gate even after our scheduled entry.

Just sat on the run way after we arrived early

New Max 10, first class seats have been shrunk. End of a 20 hour journey, it was United not Lufthansa, just glad to get home

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.

My overall experience with British Airways was good. The cabin crew were friendly and helpful, and the flight was comfortable. The food was average and could be improved, but overall, I had a pleasant experience.

Cabin staff were very disengaged, spoke with no eye contact, dismissive. Disappointing compared to my United experiences.

awful delay, awful communication, zero updates throughout the experience of a giant delay

It was decent, there was no WiFi on the flight but the FA’s gave everyone a warning once we boarded the plane. Unfortunately it didn't give me enough time to download my entertainment content.

On Time. AA is late due to maintenance all the time.

Seats were very tight for a 17 hour flight. Baby cried for 15 out of 17 hours.

Flight attendant super rude demanding I remove my carry on baggage from overhead and place under seat. I stated I am an ADA passenger and need the leg room as the seats are very tight. That’s why I boarded early for the extra time to get situated. She said, we need the space. I replied “How can that be as only a few passengers have boarded so far? I am executive platinum status so I understand the rules and you are discriminating against ADA federal law. Please stop”. Her answer… then you should find another flight! Not ok. Addressed with senior flight attendant. So unprofessional and discriminatory.

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