$463 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 7/31. 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 Cana2 stops$1,213
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$764
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239
Punta Cana
Punta Cana2 stops$1,213
Santo Domingo
Santo Domingo2 stops$953
Nassau
Nassau2 stops$764
Kingston
Kingston2 stops$1,188
Puerto Plata
Puerto Plata2 stops$1,239

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

Mon, Aug 17 - Mon, Aug 24
Multiple Airlines Logo
1:29 am - 8:40 pm
ANC
-
NAS
15h 11m
2 stops
Multiple Airlines Logo
7:45 am - 9:36 am
NAS
-
ANC
29h 51m
2 stops
$764Multiple Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
9:22 pm - 10:16 pm
ANC
-
NAS
20h 54m
2 stops
American Airlines Logo
7:30 am - 7:09 pm
NAS
-
ANC
15h 39m
2 stops
$767American Airlines
Sat, Oct 31 - Sat, Nov 7
American Airlines Logo
9:22 pm - 2:43 pm
ANC
-
NAS
13h 21m
2 stops
American Airlines Logo
4:10 pm - 7:09 pm
NAS
-
ANC
30h 59m
1 stop
$793American Airlines
Tue, Aug 25 - Sun, Aug 30
United Airlines Logo
9:20 pm - 2:44 pm
ANC
-
SJU
13h 24m
1 stop
United Airlines Logo
1:00 am - 1:04 pm
SJU
-
ANC
16h 04m
2 stops
$815United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
11:09 pm - 2:44 pm
ANC
-
SJU
35h 35m
2 stops
United Airlines Logo
3:56 pm - 7:59 pm
SJU
-
ANC
32h 03m
1 stop
$818United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
11:09 pm - 2:44 pm
ANC
-
SJU
35h 35m
2 stops
United Airlines Logo
3:56 pm - 7:59 pm
SJU
-
ANC
32h 03m
1 stop
$822United 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
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
$835Delta
Wed, Aug 19 - Wed, Aug 26
United Airlines Logo
3:15 pm - 12:54 pm
ANC
-
SJU
17h 39m
2 stops
United Airlines Logo
7:00 am - 7:35 pm
SJU
-
ANC
16h 35m
2 stops
$844United Airlines
Fri, Sep 25 - Mon, Sep 28
Delta Logo
2:28 pm - 1:38 pm
ANC
-
SJU
19h 10m
2 stops
Delta Logo
7:30 am - 12:27 am
SJU
-
ANC
20h 57m
2 stops
$855Delta
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 $671, 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

$463
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 8476 reviews
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

10.0 ExcellentAnonymous, Jul 2026
DTW - ATL
Read more Delta reviews

Weather in Atlanta necessitated an hour's hold on the tarmac before we could leave Detroit. The plane was packed, and I expected some surliness. But no! The crew was fantastic (jovial even!), responsive to people's needs, and kept us informed. Consequently, the passengers took the delay in stride, and what could have been an ugly situation turned out to be no more than a minor inconvenience. The crew were the stars here.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

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

Our flight gor canceled and there was no one to help us but told us to scan the qr code and fill the forms on-line. Very poor service especially we are tourists traveling to Washington DC for the 1st time.

1. Everything was satisfactory concerning the flight. 2. Can't think of what could be better right now.

Onboard staff was courteous, helpful, responsive and friendly. The boarding process was disorganized, poorly communicated, and disheveled. Gate agents were yelling instead of using the PA system, didn’t communicate the timing delay of our flight, and created an atmosphere of chaos rather than order and communication. As far as I know, there was no reason for their. I would hate to see how it operated under extreme conditions. I’ve never seen United Airlines operations in such a state.

Baggage claim signs were not updated with my flight information, so I had to guess. The app wasn't updated either.

I almost missed my connection in Chicago due to having to wait on a gate to be open I am assuming. Having to run from E terminal to C terminal and I barely made it there before they closed the door. This may not be the actual airline's fault it's crazy how there is so little time between flight especially when they are placed so far apart in the airport.

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.

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.

They cancelled our flight two times after rebooking us for a later flight. We never got on the plane. We found another solution by driving.

Quick flight. No time to stress over it. Over before it begins.

Very good, boarded and took off on time and landed early

It was good overall but when I book my flight and seat through Kayak, AA will at times change those seats during check-in time which I don’t understand why. I always book aisle seats and had to sit at window for my flight to Austin this trip.

Mostly great. Only issue was with the WiFi. Halfway through the flight it was spotty and I was unable to work as I planned. This impacted my work products as I am traveling for business and it was an unexpected hindrance which was inconvenient. Flight here was amazing. For a 5 hour flight something more than a Biscoff would be nice but I’m just swinging at windmills I guess…

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports