$355 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 8/31. 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.
1 adult
1 adult, Economy, 0 bags

Save 20% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Flight Deals
Booking Insights
Flight Deals

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$853
Santo Domingo
Santo Domingo2 stops$993
Nassau
Nassau2 stops$795
Kingston
Kingston2 stops$1,157
Punta Cana
Punta Cana2 stops$853
Santo Domingo
Santo Domingo2 stops$993
Nassau
Nassau2 stops$795
Kingston
Kingston2 stops$1,157

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

Tue, Aug 25 - Fri, Sep 4
United Airlines Logo
9:20 pm - 11:50 pm
ANC
-
SJU
22h 30m
2 stops
United Airlines Logo
1:00 am - 7:59 pm
SJU
-
ANC
22h 59m
2 stops
$786United Airlines
Tue, Aug 25 - Fri, Sep 4
United Airlines Logo
9:20 pm - 11:50 pm
ANC
-
SJU
22h 30m
2 stops
United Airlines Logo
1:00 am - 7:59 pm
SJU
-
ANC
22h 59m
2 stops
$790United Airlines
Wed, Aug 26 - Wed, Sep 2
United Airlines Logo
8:00 pm - 1:33 pm
ANC
-
NAS
13h 33m
2 stops
United Airlines Logo
12:35 pm - 11:59 pm
NAS
-
ANC
15h 24m
2 stops
$795United Airlines
Tue, Jan 19 - Thu, Jan 28
Delta Logo
5:15 pm - 2:05 pm
ANC
-
SJU
15h 50m
2 stops
Delta Logo
3:15 pm - 1:45 am
SJU
-
ANC
15h 30m
2 stops
$825Delta
Sun, Jan 17 - Thu, Jan 28
Delta Logo
9:55 pm - 5:20 pm
ANC
-
SJU
14h 25m
2 stops
Delta Logo
3:15 pm - 1:45 am
SJU
-
ANC
15h 30m
2 stops
$825Delta
Sun, Jan 17 - Thu, Jan 28
Delta Logo
9:55 pm - 2:15 pm
ANC
-
SJU
11h 20m
1 stop
Delta Logo
7:30 am - 9:03 pm
SJU
-
ANC
18h 33m
2 stops
$825Delta
Wed, Aug 26 - Thu, Sep 3
Multiple Airlines Logo
2:28 am - 7:54 pm
ANC
-
PUJ
37h 26m
2 stops
Multiple Airlines Logo
7:30 pm - 11:12 am
PUJ
-
ANC
19h 42m
1 stop
$853Multiple Airlines
Fri, Aug 28 - Fri, Sep 4
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
$855Southwest
Wed, Sep 23 - Fri, Oct 2
American Airlines Logo
8:20 pm - 2:15 pm
ANC
-
STI
13h 55m
2 stops
American Airlines Logo
3:15 pm - 8:49 pm
STI
-
ANC
33h 34m
2 stops
$958American Airlines
Fri, Nov 13 - Fri, Nov 20
American Airlines Logo
8:14 pm - 12:16 am
ANC
-
SJU
23h 02m
1 stop
American Airlines Logo
6:28 am - 7:17 pm
SJU
-
ANC
17h 49m
1 stop
$975American 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 $690, 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 July and December, when the average cost of round-trip tickets is $1,375 and $1,275 respectively.

Good to know

Low season

April

Cheapest flight

$355
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 9% 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 8501 reviews
7.8Comfort
8.1Boarding
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

2.0 MediocreAidan, Jul 2026
RDU - BOS
Read more Delta reviews

Awful. There was an unexpected delay of nearly three hours because there were not enough flight attendants. I understand this is likely due to FAA regulations; but in that case, Delta should coordinate with smaller airports such as RDU to have extra flight attendants on the ground and "on call". In addition, this was the second 2-hour+ delay to Boston on this route in one week.

It was strange that the flight attendant was so adamant about having phones turned to airplane mode that he was calling out names from networks shown and waiting until they were all gone. I've never experienced that before, and after already working through an hour+ delay, it felt tone deaf. I take dozens of flights per year and have never experienced anything similar.

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’m an EP on AA every year for more than a decade but this was a very pleasant and surprising experience. Clean and sizable plane for HOU to CHI. 5 row first class. And excellent food in first class the steak option was really good. Your flight attendants even better. Seat 5A

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

My flight was delayed so bad i missed u it so i just said never mind

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

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.

This flight 1810 on 7/30 from EWR to DFW got 4 hours delay. this round trip experience is bad, my AA flight 618 from DFW to EWR on 7/28 was redirected to PIT and totally delayed about 9 hours due to mixed of weather and AA IT outage and then on the way back delayed for 4 hours. Lucky, i changed my flight to UA on the way back. i don't like AA anymore. i will consider other airline options in the future.

Bad experience going to DFW with an IT outage then bad on the way back with a nearly 5 hour delay that’s started as maintenance then caused us to wait further due to weather - which would not have happened if we had left on time.

IT issues created a mess had you change my flight and your system never changed it

Horrible experience flying with American. Flight was delayed due to inbound flight delay. Fine, it happens. Then, we were delayed an additional almost 30 minutes due to the paperwork for departure having a "clerical error." Then, upon landing at the destination airport we were stuck on the plane for an HOUR after we landed and pulled up to the gate because apparently there was another plane. An hour waiting for the gate 12:30 AM when the flight has already been delayed due to operational error feels like a complete failure of the ability to do the one thing they need to do apart from actually have the plane takeoff and land. Very disappointing.

It was a 3 hour flight from Dallas to Missoula. The aircraft did not have power plugs, internet or in-flight entertainment. When boarding, one flight attendant was "somewhere in the airport" so delayed the boarding process (not coming from another flight) although we did take off on time and landed early. In flight there was little to no service - we got the standard beverage but no real connection with the crew which feels unusual for a 3 hour flight. A passenger needed help stowing her bag and got no assistance, and actually some passive aggressive comments from the flight attendants about "she needs to remove the extender" and "she'll have to find a place for it". I have seen others be helpful and put a bag in the closet, or support assistance as the boarding door was already closed. Just not a great experience considering the cost of my round trip ticket {$1000}.

Disorganized boarding. Mandatory to gate check bags. Curt flight staff. No space for cabin bag, even when I was in first class.

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