$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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1 adult, Economy, 0 bags

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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$973
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,180
Punta Cana
Punta Cana1 stop$862
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,180

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, Aug 21 - Fri, Aug 28
American Airlines Logo
9:56 pm - 7:11 pm
ANC
-
NAS
17h 15m
2 stops
American Airlines Logo
7:45 am - 8:51 pm
NAS
-
ANC
17h 06m
2 stops
$747American Airlines
Tue, Aug 25 - Fri, Sep 4
United Airlines Logo
3:15 pm - 1:45 pm
ANC
-
SJU
18h 30m
2 stops
United Airlines Logo
1:00 am - 7:59 pm
SJU
-
ANC
22h 59m
2 stops
$780United Airlines
Tue, Sep 22 - Thu, Sep 24
United Airlines Logo
8:00 pm - 11:50 pm
ANC
-
SJU
23h 50m
2 stops
United Airlines Logo
1:00 am - 10:43 pm
SJU
-
ANC
25h 43m
2 stops
$782United Airlines
Tue, Sep 22 - Fri, Sep 25
United Airlines Logo
8:00 pm - 11:50 pm
ANC
-
SJU
23h 50m
2 stops
United Airlines Logo
3:56 pm - 7:57 pm
SJU
-
ANC
32h 01m
1 stop
$798United Airlines
Tue, Sep 22 - Fri, Sep 25
United Airlines Logo
8:00 pm - 11:50 pm
ANC
-
SJU
23h 50m
2 stops
United Airlines Logo
3:56 pm - 7:57 pm
SJU
-
ANC
32h 01m
1 stop
$800United Airlines
Tue, Sep 22 - Fri, Sep 25
United Airlines Logo
8:00 pm - 11:50 pm
ANC
-
SJU
23h 50m
2 stops
United Airlines Logo
3:56 pm - 10:43 pm
SJU
-
ANC
34h 47m
2 stops
$805United 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
Sun, Oct 4 - Sun, Nov 8
Delta Logo
2:28 pm - 12:26 pm
ANC
-
STI
17h 58m
2 stops
Delta Logo
8:16 pm - 10:36 pm
STI
-
ANC
31h 20m
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
Fri, Aug 21 - Fri, Aug 28
Air Canada Logo
2:40 pm - 5:30 pm
ANC
-
NAS
22h 50m
3 stops
Air Canada Logo
6:30 pm - 1:38 pm
NAS
-
ANC
23h 08m
2 stops
$1,314Air Canada
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 and prices are also 4% lower on average.
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 8456 reviews
7.8Comfort
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
Airline reviews

It was okay. We were delayed for weather reasons, but the pilots and the flight control staff figured a way around the storm and were able to get us to Los Angeles safely. Not all the staff members were polite, but the entertainment on the flight was good.

6.0 GoodBridget, Jul 2026
ATL - LAX
Read more Delta reviews

It was okay. We were delayed for weather reasons, but the pilots and the flight control staff figured a way around the storm and were able to get us to Los Angeles safely. Not all the staff members were polite, but the entertainment on the flight was good.

So terrible. My flight was 4 hours delayed and we weren't notified til last second within an hour of boarding. WE had to sit on the plane for 4 hours. ridiculous.

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 head rest is too big and cannot be placed differently/removed. Causes one head to tilt forward and increase back pain

We sat on the hot plane for ours with very conflicting messages. Some (most?) of this may be due to the flight control staff, but we were also repeatedly getting "we are leaving"/"we are not" messages. It was very uncomfortable

It was terribly delayed with zero support from united airlines. I reached at 1 am in the night. They did not provide any option to change the flights.

It was great. All the crew were professional and nice.

Flight was delayed 14 hours due to DC air show and weather. Missed connection to MUC.

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

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.

Over the course of 7 months of travel, I can count on my hand the number of times the flight has departed on time. Majority of the instances have been related to non-weather reasons. Would not recommend flying this Airline

Efficiency of supporting mechanical teams who changed a wheel on airplane in minutes. So no delay, and pilot made up the lost minutes in flight. Comfortable seat.

Comfort in premium economy is worth it for long hauls especially on the 787-9P Dreamliner with the modern updates. The food was okay. All 4 of us selected the same meal, 2 of us had very dry hard to cut chicken, the other 2 were tender and good. The sides/salad/dessert all very good as far as airline food goes. Crew were very attentive. Will be hard to ever go back to regular economy!

Flight attendants and crew were great! This plane was fine. It was clean and everything worked properly. Now, the gate change was not communicated. No text or information. It wasn't far with the gate change but it still changed without any communication. Not sure if this is on American or Kayakl. Also, internet was the worst. I would never have ATT. 3+hr flight and weak internet. I think I watched the commercials to get on at least 6 times. Terrible internet!

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

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