$383 Find Cheap Flights from Anchorage to Caribbean Islands - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Anchorage to Caribbean Islands departing on 8/10. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
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Cheap Flights from Anchorage to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$862
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau1 stop$747
Saint Thomas Island
Saint Thomas Island2 stops$2,534
Kingston
Kingston2 stops$4,340
Punta Cana
Punta Cana1 stop$862
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau1 stop$747
Saint Thomas Island
Saint Thomas Island2 stops$2,534
Kingston
Kingston2 stops$4,340

Book Cheap Anchorage to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Anchorage to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Anchorage to Caribbean Islands

Fri, Dec 4 - Thu, Dec 10
United Airlines Logo
11:40 pm - 4:14 pm
ANC
-
NAS
12h 34m
1 stop
United Airlines Logo
2:55 pm - 10:39 pm
NAS
-
ANC
35h 44m
2 stops
$747United Airlines
Tue, Sep 1 - Fri, Sep 4
United Airlines Logo
3:15 pm - 1:45 pm
ANC
-
SJU
18h 30m
2 stops
United Airlines Logo
1:25 pm - 1:04 pm
SJU
-
ANC
27h 39m
2 stops
$775United Airlines
Tue, Sep 1 - Fri, Sep 4
United Airlines Logo
9:20 pm - 11:50 pm
ANC
-
SJU
22h 30m
2 stops
United Airlines Logo
4:55 pm - 1:04 pm
SJU
-
ANC
24h 09m
2 stops
$777United Airlines
Fri, Aug 21 - Sun, Aug 30
Southwest Logo
10:25 pm - 6:15 pm
ANC
-
SJU
15h 50m
2 stops
Southwest Logo
6:35 am - 10:45 pm
SJU
-
ANC
20h 10m
2 stops
$825Southwest
Wed, Aug 12 - Tue, Aug 25
Multiple Airlines Logo
11:21 pm - 12:30 pm
ANC
-
PUJ
33h 09m
1 stop
Multiple Airlines Logo
9:38 am - 1:38 am
PUJ
-
ANC
20h 00m
2 stops
$862Multiple Airlines
Tue, Aug 11 - Sun, Aug 23
Multiple Airlines Logo
7:08 pm - 10:36 am
ANC
-
PUJ
35h 28m
2 stops
Multiple Airlines Logo
6:00 pm - 11:12 am
PUJ
-
ANC
21h 12m
1 stop
$917Multiple Airlines
Wed, Sep 23 - Fri, Oct 2
Delta Logo
2:28 pm - 5:59 pm
ANC
-
STI
23h 31m
2 stops
Delta Logo
1:55 pm - 1:38 pm
STI
-
ANC
27h 43m
2 stops
$949Delta
Mon, Oct 26 - Mon, Nov 16
Delta Logo
2:23 pm - 1:41 pm
ANC
-
SDQ
19h 18m
2 stops
Delta Logo
3:55 pm - 1:40 pm
SDQ
-
ANC
26h 45m
2 stops
$971Delta
Mon, Aug 10 - Mon, Aug 24
American Airlines Logo
9:56 pm - 6:44 pm
ANC
-
SDQ
16h 48m
2 stops
American Airlines Logo
7:00 am - 10:32 pm
SDQ
-
ANC
19h 32m
2 stops
$973American Airlines
Mon, Aug 10 - Sun, Aug 23
American Airlines Logo
9:56 pm - 6:44 pm
ANC
-
SDQ
16h 48m
2 stops
American Airlines Logo
7:00 am - 10:32 pm
SDQ
-
ANC
19h 32m
2 stops
$978American Airlines
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?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $665, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Anchorage to Caribbean Islands is April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are February and May, when the average cost of round-trip tickets is $1,161 and $1,161 respectively.

Good to know

Low seasonApril
Cheapest flight$383
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 11% increase in price.
Flight from Anchorage to Santo Domingo

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

 
See real verified KAYAK customer reviews for airlines flying from Anchorage to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
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 8462 reviews
7.8Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

We never made it on this flight because we missed our connection due to o delayed flight from Jackson.

2.0 MediocreAnonymous, Jul 2026
SLC - SJC
Read more Delta reviews

We never made it on this flight because we missed our connection due to o delayed flight from Jackson.

We had a terrible experience. The flight was delayed several hours, so we missed our connection. We were told to wait at the airport. At around 11:00 pm, the flight was cancelled. There were no available seats out of Jackson for the next two days. Fortunately, we had the foresight to rebook on United for the next day. However, we had to spend a long day at the airport and an overnight at a mediocre hotel. It was a miserable way to spend part of our vacation. We also sacrificed our $450 deposit on our California hotel because we could not get there.

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

The seats on this flight weren’t as comfortable as we had expected. Even leaned back these seats left us feeling crappy in our backs. Also we had to use our own tablets for movies, but nothing in the seats in front of us to hold the tablets up.

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

Flight was delayed “due to earlier delays of that plane”, so we were nearly three hours late.

There was a piece of plastic baked into my buttermilk biscuit! I have a pictures. The flight attendants in first class were really apologetic, and tried to rectify the situation. I I am very appreciative that they were able to give me some packets of pretzels and gummy bears. I understand they don't personally handle the food until warming it up so I know it wasn't their fault. I don't know whether it was a newer aircraft, or different food packaging, but I was happy that when the food was being warmed up - it didn't smell like plastic. Jokes on me with finding plastic in my food.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

The seats were very uncomfortable. I paid for the front economy. i swear they added a row of seats in there. It was so tight, that I could measure the distance between my seat and the one in front from my elbow to the tips of my fingers plus six inches. The seat cushion was completely worn out. The dinner was very good. Thank you for having a vegetarian option as a standard. But breakfast was nothing but sugar. that's not food. The crew was crabby and rude, especially in regards to coming to the back gallery. And the entertainment choice: why would you put violent movies on the choice? the Godfather? Some movies with black women being beaten over the head with clubs? What the heck? You know that when there is a movie on a plane, everyone gets to watch it. Why choose the most violent titles possible? The total number of movies were very limited, and the television, even more so. No games were available on the set. The wellness section was nice, thank you. I appreciated a galley in the middle where I could stand. The seats were unbearable.

The seats were uncomfortable, as if the cushions haven't been switched out in many years. I felt like I was on an old bus. The food was delicious. thank you. Onboard entertainment, very limited. Unless you like violent movies. Why in the world would you have such severely violent movies on a plane? if you don't want to see such things, you don't have a choice. Have you considered that when choosing entertainment? Good god. Why would you have the Godfather? Or black women being brutally beaten with a club? Why in the hell would you put that kind of material on a plane? As for Kayak: Why when I ordered Qantas, was the plane on United?

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.

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

It’s love good long way travel!! I always want more give me price down i want ever month travel I miss travel only North Carolina to Thailand in my love her !!

The departure and arrival was on time. The fact that I could load my boarding tickets on the American airlines app.

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

Entertainment was very plentiful, staff were courteous. Seating was HORRIBLE. That is the most cramped I’ve ever been on any flight …Jet Blue and Spirit included. Very uncomfortable for a six hour trip.

Pros: "This was the worst flying experience I have ever encountered."
Cons: "We sat on the tarmac 3 hours, then deplaned to a holding area for another hour and then were told the flight would be delayed until 1 pm the next day. I booked this flight in order to arrive home 7 hours earlier than originally planned on Alaska Air. I finally arrived 20 hours LATER THAN I WOULD HAVE ARRIVED!"

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports