$421 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 7/24. 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.
1 adult
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 Cana2 stops$1,141
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau2 stops$767
Kingston
Kingston2 stops$4,360
Punta Cana
Punta Cana2 stops$1,141
Santo Domingo
Santo Domingo2 stops$973
Nassau
Nassau2 stops$767
Kingston
Kingston2 stops$4,360

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

Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
9:22 pm - 9:09 pm
ANC
-
NAS
19h 47m
2 stops
American Airlines Logo
7:30 am - 7:16 pm
NAS
-
ANC
15h 46m
2 stops
$767American Airlines
Mon, Aug 31 - Mon, Sep 7
American Airlines Logo
9:56 pm - 7:11 pm
ANC
-
NAS
17h 15m
2 stops
American Airlines Logo
7:45 am - 10:32 pm
NAS
-
ANC
18h 47m
2 stops
$822American Airlines
Tue, Aug 25 - Sat, Sep 5
United Airlines Logo
3:15 pm - 1:45 pm
ANC
-
SJU
18h 30m
2 stops
United Airlines Logo
3:56 pm - 3:10 pm
SJU
-
ANC
27h 14m
2 stops
$828United Airlines
Fri, Aug 14 - Fri, Aug 21
United Airlines Logo
11:09 pm - 5:38 pm
ANC
-
SJU
14h 29m
1 stop
United Airlines Logo
7:00 am - 7:02 pm
SJU
-
ANC
16h 02m
1 stop
$835United Airlines
Mon, Aug 24 - Sat, Sep 5
Delta Logo
1:32 am - 10:29 pm
ANC
-
SJU
16h 57m
2 stops
Delta Logo
7:00 am - 7:00 pm
SJU
-
ANC
16h 00m
1 stop
$855Delta
Thu, Aug 13 - Thu, Aug 27
Southwest Logo
10:25 pm - 10:10 pm
ANC
-
SJU
19h 45m
2 stops
Southwest Logo
5:30 am - 9:15 pm
SJU
-
ANC
19h 45m
2 stops
$865Southwest
Fri, Aug 14 - Fri, Aug 21
Southwest Logo
10:25 pm - 6:15 pm
ANC
-
SJU
15h 50m
2 stops
Southwest Logo
5:30 am - 9:15 pm
SJU
-
ANC
19h 45m
2 stops
$890Southwest
Wed, Sep 23 - Fri, Oct 2
Delta Logo
10:10 pm - 5:59 pm
ANC
-
STI
15h 49m
2 stops
Delta Logo
7:30 pm - 6:50 pm
STI
-
ANC
27h 20m
2 stops
$969Delta
Wed, Dec 9 - Mon, Dec 14
Multiple Airlines Logo
1:27 am - 8:45 pm
ANC
-
NAS
15h 18m
2 stops
Multiple Airlines Logo
8:30 am - 12:10 am
NAS
-
ANC
19h 40m
2 stops
$1,057Multiple Airlines
Wed, Sep 23 - Fri, Oct 2
Multiple Airlines Logo
8:20 pm - 2:15 pm
ANC
-
STI
13h 55m
2 stops
Multiple Airlines Logo
3:15 pm - 1:36 pm
STI
-
ANC
26h 21m
3 stops
$1,164Multiple 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 $674, 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 December and May, when the average cost of round-trip tickets is $1,275 and $1,261 respectively.

Good to know

Low season

April

Cheapest flight

$421
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from Anchorage to San Juan

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 8477 reviews
8.1Boarding
7.2Food
8.5Crew
7.8Entertainment
7.8Comfort
Airline reviews

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

2.0 MediocreJacob, Jul 2026
ATL - RIC
Read more Delta reviews

Seat was too small for someone as tall as I am. I was behind an exit row making my leg room even less. There flights were delayed by multiple hours. Some weather related and others staff related. The plane was hot. Horrible experience.

The Atlanta airport had thunderstorms, which caused our flight to be delayed by multiple hours. Once we were able to board.the gate agent was rude and was trying to rush us onto the plane because the team in the plane was about to run out of hours once we were all aboard the plane they ran into an issue where the catering truck was filling up the back of the plane and they left and had to come back because they didn’t fill it up all the way, causing even more of a delay. My seat was very tight. I didn’t have a lot of legroom overall this was a miserable 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

Unbelievably smooth boarding at IAH and the flight attendants were top notch.

We flew business fares. Was amazing. However, the check in didn't offer business fares preboarding which is less hectic. 8/10 due to this. Staff compared to Canadian carriers go above and beyond. Would gladly fly United again.

It was extremely hot in the cabin the entire flight, vent air was worn

The Wi-Fi did not work, so you weren't able to watch entertainment on your own device. They did not have wired headphones so you couldn't watch it on the in-seat entertainment screen either. There was plenty of time to do a drink and snag service but the flight attendants chose not to.

Great experience, boarding was fast and efficient, so much so that we arrived to Chicago very early

Comfortable seating POS to IAH. Food options were satisfactory. Good seat from IAH to ANC. Food options could be better.

The flight did not have its customary snacks during the flight. Apparently they were never loaded on the plane.

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.

Not one thing to like. Three flights all with “mechanical” delays. Never got to where I was going and spent additional $500 for a hotel room. American Airlines is the worst in the industry!

the seat was not padded at all - uncomfortable after a 3 hour flight

This flight was of course delayed because American cannot have flights that are not delayed.

Well, true to American Airlines, both of my flights were delayed. But it’s a good thing that American is so consistently incompetent because if the first flight was delayed in the second flight was on time then I might’ve had a problem..

I sat at the airport all night from 8 pm until midnight. The airline kept delaying the flight. They also kept moving us to different gates - 4 times. Then they told us we didn’t have a pilot so we had to wait. Then they cancelled the flight at midnight! I ended up having to rent a car to drive home. So i ended up not even being able to fly on the flight i paid for. Ridiculous, and no agents could help at all. I will not ever book this flight.

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