$338 Find Cheap Flights from Anchorage to Caribbean

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 departing on 7/7. 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

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$1,034
Santo Domingo
Santo Domingo2 stops$1,060
Nassau
Nassau2 stops$709
Saint Thomas Island
Saint Thomas Island2 stops$1,109
Kingston
Kingston2 stops$1,197
Puerto Plata
Puerto Plata2 stops$1,187
Punta Cana
Punta Cana2 stops$1,034
Santo Domingo
Santo Domingo2 stops$1,060
Nassau
Nassau2 stops$709
Saint Thomas Island
Saint Thomas Island2 stops$1,109
Kingston
Kingston2 stops$1,197
Puerto Plata
Puerto Plata2 stops$1,187

Book Cheap Anchorage to Caribbean 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 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

Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
9:53 pm - 7:30 pm
ANC
-
NAS
17h 37m
2 stops
American Airlines Logo
11:03 am - 11:52 pm
NAS
-
ANC
16h 49m
2 stops
$709American Airlines
Tue, Aug 4 - Tue, Aug 18
Southwest Logo
11:15 pm - 9:05 pm
ANC
-
SJU
17h 50m
2 stops
Southwest Logo
6:00 am - 10:05 pm
SJU
-
ANC
20h 05m
2 stops
$790Southwest
Tue, Sep 1 - Thu, Oct 1
Delta Logo
8:30 pm - 1:30 pm
ANC
-
SJU
13h 00m
1 stop
Delta Logo
7:30 am - 10:22 pm
SJU
-
ANC
18h 52m
2 stops
$815Delta
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
8:17 pm - 5:05 pm
ANC
-
NAS
16h 48m
1 stop
American Airlines Logo
12:47 pm - 8:47 pm
NAS
-
ANC
12h 00m
1 stop
$822American Airlines
Sun, Apr 26 - Wed, Apr 29
United Airlines Logo
8:50 pm - 11:50 pm
ANC
-
SJU
23h 00m
2 stops
United Airlines Logo
1:00 am - 5:01 pm
SJU
-
ANC
20h 01m
2 stops
$834United Airlines
Thu, Sep 17 - Sat, Sep 19
United Airlines Logo
3:30 pm - 3:42 pm
ANC
-
SJU
20h 12m
2 stops
United Airlines Logo
1:00 am - 3:04 pm
SJU
-
ANC
18h 04m
2 stops
$835United Airlines
Sat, Apr 25 - Wed, Apr 29
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:59 pm - 5:01 pm
NAS
-
ANC
29h 02m
1 stop
$837United Airlines
Tue, Apr 21 - Tue, Apr 28
Delta Logo
1:41 pm - 11:45 am
ANC
-
SJU
18h 04m
2 stops
Delta Logo
7:15 am - 12:25 am
SJU
-
ANC
21h 10m
2 stops
$860Delta
Sun, May 10 - Sun, May 17
Multiple Airlines Logo
10:26 am - 10:15 am
ANC
-
PUJ
19h 49m
2 stops
Multiple Airlines Logo
6:00 pm - 11:53 am
PUJ
-
ANC
21h 53m
1 stop
$1,034Multiple Airlines
Sat, Aug 8 - Sat, Aug 15
Air Canada Logo
2:40 pm - 5:30 pm
ANC
-
NAS
46h 50m
2 stops
Air Canada Logo
6:30 pm - 1:38 pm
NAS
-
ANC
23h 08m
2 stops
$1,112Air Canada
Booking Insights

KAYAK's insights & trends for Anchorage to Caribbean flights

Get data-powered insights and trends into flights from Anchorage to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Anchorage to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Anchorage to Caribbean were found on American Airlines ($709) and Southwest ($790).

Good to know

Low seasonAugust
Cheapest flight$338
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from Anchorage to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Anchorage to Caribbean?

    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.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Anchorage to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Anchorage to Caribbean 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?

    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 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?

    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 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

 
Need help choosing which airline to fly with from Anchorage to Caribbean? 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.
7.9
DeltaOverall score based on 8356 reviews
7.2Food
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
Airline reviews

I am still at the Airport! Delayed Delayed and Delyaed

2.0 MediocreSaeed, Mar 2026
JFK - CHS
Read more Delta reviews

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The cabin temperature was nice and cool. The wifi was not working.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

As previously noted, this flight was great: departure was timely, the crew was friendly and attentive, and wifi connectivity was seamless. In particular, I appreciated that the flight attendant just told me to stow the laptop right before takeoff/landing, and trusted me to do so (which I did!).

Kayak botched up the booking, i had to call delta and fix. In the process Delta failed to honor my comfort plus seat assignment that i had previously.

3 hour delay…. Nearly 2 hours sitting on tarmac. Do better, United. Or at least have the sense to not say “we hope you enjoyed your flight with us” upon disembarking.

Flights were on time. Free Wifi on plane. Everything was well organized.

During landing. 2 crew members passed 3 times by my lane and didn't notice that people in front of us had their site to the furthermore reclined... That was uncomfortable and could have been dangerous.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

We had excellent customer service despite the chaos at George Bush airport in Houston!

It isvvery small flight. No leg room . No space to put my personal item at feet.

I will never fly ANA again. They lost one of my large pieces of checked luggage, the heaviest one with the most valuable items in it, and they said they will not send me an email unless they can't find it, even though the paper they gave me to track the status of my lost luggage requires a code from an email they are supposed to send me so I can do baggage tracing. They claim to be an international airline, but they also insist on calling a Japanese telephone number to confirm where to send the lost baggage if they find it. It is impossible to find an actual contact email address for customer support on their website, and their AI chatbot is unhelpful, directing you to a webpage that says it is for contact information but does not have any actual email addresses or phone numbers listed on it. My seat in economy did not recline at all, even though I was not sitting in an exit row nor the very back row. I had to sit in the fully upright position for over ten hours of international travel. Awful experience overall.

No seat back entertainment. And app had a hard time getting entertainment loaded.

ticket agent lady wás very helpful , she arranged wheel chair for my elderly mother

Didn't make the flight because the first leg of my flight was canceled and the next leg was already booked.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Delays with no explanation. It could have been handled better.

Ceiling fell down and had to have maintenance come and duct tape it up. No WiFi on the flight.

A first class seat should fit a fat person, and this doesn't. The trays in the armrest are less functional than an ordinary tray in the back of the seat.

The flight attendant was friendly and efficient. The temperature was kept nice and cool. The plane was nice, but filthy. There were visible spills on my tray table. The gate agent was somewhat rude with her announcements and in speaking with other customers.

I appreciate that I finally got the seat I paid extra for this time. Thank you

I would have liked a pillow. The vegetarian wrap and oaten cake was good.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports