$304 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 8/17. 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$983
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau2 stops$913
Kingston
Kingston2 stops$1,180
Punta Cana
Punta Cana2 stops$983
Santo Domingo
Santo Domingo2 stops$971
Nassau
Nassau2 stops$913
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

Tue, Aug 18 - Tue, Aug 25
Southwest Logo
11:55 pm - 9:05 pm
ANC
-
SJU
17h 10m
2 stops
Southwest Logo
8:20 am - 9:15 pm
SJU
-
ANC
16h 55m
2 stops
$790Southwest
Tue, Aug 18 - Tue, Aug 25
United Airlines Logo
8:15 pm - 12:54 pm
ANC
-
SJU
12h 39m
1 stop
United Airlines Logo
7:00 am - 7:02 pm
SJU
-
ANC
16h 02m
1 stop
$815United Airlines
Mon, Aug 24 - Fri, Aug 28
United Airlines Logo
9:20 pm - 1:45 pm
ANC
-
SJU
36h 25m
2 stops
United Airlines Logo
3:56 pm - 7:59 pm
SJU
-
ANC
32h 03m
1 stop
$820United Airlines
Sun, Aug 30 - Sat, Sep 5
United Airlines Logo
8:00 pm - 1:45 pm
ANC
-
SJU
37h 45m
2 stops
United Airlines Logo
3:56 pm - 3:10 pm
SJU
-
ANC
27h 14m
2 stops
$821United Airlines
Sun, Aug 16 - Sun, Aug 23
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
$913American 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
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 - 7:13 pm
STI
-
ANC
31h 58m
2 stops
$967American Airlines
Mon, Oct 26 - Mon, Nov 16
Delta Logo
11:30 am - 12:24 pm
ANC
-
SDQ
20h 54m
2 stops
Delta Logo
3:55 pm - 10:16 am
SDQ
-
ANC
23h 21m
2 stops
$971Delta
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
$1,166Multiple Airlines
Tue, Dec 15 - Tue, Jan 12
Multiple Airlines Logo
4:30 pm - 2:32 pm
ANC
-
PUJ
17h 02m
2 stops
Multiple Airlines Logo
2:31 pm - 1:38 pm
PUJ
-
ANC
28h 07m
2 stops
$1,253Multiple 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$304
Best time to beat the crowds with an average 12% 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 8454 reviews
8.5Crew
8.1Boarding
7.8Entertainment
7.2Food
7.8Comfort
Airline reviews

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

2.0 MediocreAnonymous, Jul 2026
MCI - ATL
Read more Delta reviews

Our flight was delayed by over 4 hours due to a maintenance issue. They announced a new plane was on the way. We were given a $12 food voucher ( airport food is quite expensive You can’t even by a water and a small snack for 12:00. 4 hours later we boarded and landed in Atlanta at 10:20 ish pm. Of course we missed our connection and we were given a hotel voucher and another food voucher ! We didn’t make it home until 11:00 the next day ! Unacceptable

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

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 flight was delayed by a hour and I wish they had communicated it sooner. No issues on the plane, it did take a while for food to come.

Know that the movies that you are going to be offered are the oldest be rated movies they could possibly get. They may have one or two new movies that they keep advertising but when you’re flying 15 hours, there is nothing to see past the first new movie.

Staff could’ve been a little more cordial. The men were much more friendlier than the women. My daughter and I also missed the 2nd to last meal as we were sleeping but that is on us.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

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.

I found the seats ergonomically uncomfortable forcing the body to seat slightly hunched. For a short flight I worked on adjustments but for a longer flight, it would be difficult.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Crew was great! Food sub-bar, tepid & flavorless. No snack options on trans-atlantic flight. Premium Economy seats ok, leg rest wouldn’t stay in place.

The planes can use an actual cleaning. The armrest and seats do not appear to be cleaned on this one and most other planes.

The flight attendant was very polite and attentive. The food was good.

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