$315 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 7/21. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Anchorage to Caribbean Islands, as well as popular online travel agencies
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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$969
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,424
Puerto Plata
Puerto Plata2 stops$1,399
Punta Cana
Punta Cana2 stops$969
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau2 stops$747
Kingston
Kingston2 stops$1,424
Puerto Plata
Puerto Plata2 stops$1,399

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

Thu, Aug 6 - Thu, Aug 13
American Airlines Logo
11:41 pm - 7:11 pm
ANC
-
NAS
15h 30m
2 stops
American Airlines Logo
10:20 am - 11:53 pm
NAS
-
ANC
17h 33m
2 stops
$747American Airlines
Tue, Jul 28 - Wed, Aug 5
United Airlines Logo
11:59 pm - 2:57 pm
ANC
-
NAS
10h 58m
1 stop
United Airlines Logo
2:53 pm - 11:10 am
NAS
-
ANC
24h 17m
2 stops
$759United Airlines
Sat, Sep 5 - Sat, Sep 12
Multiple Airlines Logo
2:28 am - 7:15 pm
ANC
-
NAS
12h 47m
2 stops
Multiple Airlines Logo
7:45 am - 1:38 am
NAS
-
ANC
21h 53m
2 stops
$774Multiple Airlines
Fri, Aug 21 - Sun, Aug 30
Southwest Logo
10:25 pm - 6:15 pm
ANC
-
SJU
15h 50m
2 stops
Southwest Logo
6:35 am - 10:45 pm
SJU
-
ANC
20h 10m
2 stops
$790Southwest
Tue, Dec 1 - Tue, Dec 8
United Airlines Logo
11:40 pm - 11:53 am
ANC
-
NAS
32h 13m
2 stops
United Airlines Logo
2:55 pm - 10:39 pm
NAS
-
ANC
35h 44m
2 stops
$790United Airlines
Mon, Aug 24 - Fri, Aug 28
Southwest Logo
10:25 pm - 6:10 pm
ANC
-
SJU
15h 45m
2 stops
Southwest Logo
5:30 am - 9:15 pm
SJU
-
ANC
19h 45m
2 stops
$825Southwest
Tue, Jul 28 - Wed, Aug 5
American Airlines Logo
11:44 pm - 5:05 pm
ANC
-
NAS
13h 21m
2 stops
American Airlines Logo
10:20 am - 11:53 pm
NAS
-
ANC
17h 33m
2 stops
$928American Airlines
Sat, Oct 10 - Fri, Oct 23
Delta Logo
8:30 pm - 1:41 pm
ANC
-
SDQ
13h 11m
1 stop
Delta Logo
7:49 pm - 10:36 pm
SDQ
-
ANC
30h 47m
2 stops
$961Delta
Sat, Aug 29 - Sat, Sep 5
JetBlue Logo
8:19 pm - 12:57 pm
ANC
-
STI
12h 38m
1 stop
JetBlue Logo
6:00 am - 7:11 pm
STI
-
ANC
17h 11m
1 stop
$994JetBlue
Sat, Dec 12 - Tue, Dec 22
Delta Logo
1:10 pm - 1:30 pm
ANC
-
PUJ
19h 20m
2 stops
Delta Logo
1:55 pm - 12:53 am
PUJ
-
ANC
15h 58m
2 stops
$1,013Delta
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 $661, 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$315
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 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 8440 reviews
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
7.8Comfort
Airline reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

4.0 OkayLinda, Jun 2026
BNA - ATL
Read more Delta reviews

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

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

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

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.

2 hours delay on my flight causing me to miss my connecting flight. Cause was for maintenance. I understand maintenance is important but maintenance should be done before boarding people!

Better perks for corporate employees whom travel often and spend a lot of money with the airlines. Snacks were terrible chips crackers are ideas. Flight and crew were great comfort was fine entertainment not so great so so called status members means nothing

The flight de-boarded after being informed of a 3 hour delay. The gate agent said we could go to lounge. The flight ended up boarding 20 minutes later and I missed it.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

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