$402 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 8/11. 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$979
Santo Domingo
Santo Domingo2 stops$1,071
Nassau
Nassau2 stops$747
Punta Cana
Punta Cana1 stop$979
Santo Domingo
Santo Domingo2 stops$1,071
Nassau
Nassau2 stops$747

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, 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
Tue, Jul 28 - Wed, Aug 5
United Airlines Logo
8:00 pm - 1:29 pm
ANC
-
NAS
13h 29m
2 stops
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$811United Airlines
Mon, Aug 24 - Fri, Aug 28
United Airlines Logo
11:09 pm - 2:44 pm
ANC
-
SJU
35h 35m
2 stops
United Airlines Logo
4:55 pm - 7:59 pm
SJU
-
ANC
31h 04m
2 stops
$817United 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, Nov 8 - Fri, Nov 20
Delta Logo
1:30 am - 11:13 pm
ANC
-
SJU
16h 43m
2 stops
Delta Logo
7:15 am - 1:45 am
SJU
-
ANC
23h 30m
2 stops
$845Delta
Sun, Oct 18 - Mon, Nov 2
Delta Logo
4:02 pm - 1:21 pm
ANC
-
SJU
17h 19m
2 stops
Delta Logo
7:00 am - 8:55 pm
SJU
-
ANC
18h 55m
2 stops
$850Delta
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
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$402
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 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 8450 reviews
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
7.8Comfort
Airline reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

8.0 ExcellentAnonymous, Jul 2026
DTW - MBS
Read more Delta reviews

The flight was mostly smooth and direct (although it was 2 hours late). The glow of the flight attendant’s phone was annoying as I tried to sleep on this midnight flight.

The plane was not clean. Vomit was removed from seat-back pocket right in front of me. The flight attendants were rude to one another. 3 children were seated together with their parents across the aisle. The children fought physically with one slamming another’s head into the plane wall at one point. The parents were aware, but took no action to intervene. Delays occurred in Atlanta after boarding before takeoff, in the air, and in Detroit after landing (no ground crew assigned). Flight attendants offered no support for connecting flights. There were weather conditions on each end of the flight, but I didn’t mark down my ratings for these.

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

Boarded from a very small gate at LAX. Staff at gate had us line up, then waited 25 minutes to board without a word of explanation. Plane arrived on time then waited 20 minutes for a plane to vacate our gate. Majority of bags arrived after 15 minutes but it took an hour for a small number of remaining bags to be off-loaded despite my “priority” bag tag.

It's fine but Newark to Nashville was too long

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Horrible experience. They delayed our flight 7 hours!! We had to seat at the airport with kids on 4th July all day!

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

Excellent communication from the staff. We actually arrived early. Very friendly and professional staff.

Excellent flight. On time. Great staff. Clean and crisp cabin.

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 was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

We had multiple delays and a medical incident during the flight. We barely got a glass of water during the over 4 hours we were on the plane. Somehow first class got all of their service. It would be nice if all of your paying customers got the service they paid for.

The plane was spartan, the seats not that comfortable. It was like flying a super low budget airline. They charged for coffee!!! I have never, ever experienced that before.

Short hop but nice crew, efficient processes and all very timely

I had no problems but the changing of planes that I was supposed to be on was confusing. Maybe it would be helpful to let people know your flight changed. Not everyone understands airports or how flying works.

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