$387 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 5/17. 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

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

Travelers love KAYAK
41.299.237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$885
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau2 stops$885
Kingston
Kingston2 stops$1,055
Puerto Plata
Puerto Plata2 stops$1,343
Punta Cana
Punta Cana2 stops$885
Santo Domingo
Santo Domingo2 stops$941
Nassau
Nassau2 stops$885
Kingston
Kingston2 stops$1,055
Puerto Plata
Puerto Plata2 stops$1,343

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

Wed, May 27 - Fri, May 29
Southwest Logo
11:55 pm - 11:25 pm
ANC
-
SJU
19h 30m
2 stops
Southwest Logo
5:35 am - 10:45 pm
SJU
-
ANC
21h 10m
2 stops
$796Southwest
Wed, Jul 8 - Tue, Jul 14
Delta Logo
10:10 pm - 8:45 pm
ANC
-
SJU
18h 35m
2 stops
Delta Logo
2:05 pm - 1:55 am
SJU
-
ANC
15h 50m
2 stops
$815Delta
Sun, Aug 30 - Wed, Sep 2
United Airlines Logo
11:09 pm - 11:28 am
ANC
-
NAS
32h 19m
2 stops
United Airlines Logo
12:35 pm - 7:14 pm
NAS
-
ANC
34h 39m
2 stops
$885United Airlines
Sat, Jun 6 - Sat, Jun 13
Air Canada Logo
2:40 pm - 4:30 pm
ANC
-
PUJ
21h 50m
2 stops
Air Canada Logo
5:25 pm - 1:36 pm
PUJ
-
ANC
24h 11m
2 stops
$885Air Canada
Mon, Jun 8 - Mon, Jun 15
Air Canada Logo
2:40 pm - 4:30 pm
ANC
-
PUJ
21h 50m
2 stops
Air Canada Logo
5:25 pm - 1:36 pm
PUJ
-
ANC
48h 11m
2 stops
$887Air Canada
Sun, Sep 20 - Sun, Sep 27
American Airlines Logo
8:20 pm - 3:02 pm
ANC
-
SJU
14h 42m
1 stop
American Airlines Logo
6:30 am - 7:08 pm
SJU
-
ANC
16h 38m
2 stops
$895American Airlines
Sat, Jun 13 - Sat, Jun 20
Multiple Airlines Logo
8:52 pm - 7:15 pm
ANC
-
NAS
18h 23m
3 stops
Multiple Airlines Logo
6:30 pm - 1:38 pm
NAS
-
ANC
23h 08m
2 stops
$900Multiple Airlines
Fri, Jun 5 - Fri, Jun 26
Multiple Airlines Logo
1:22 pm - 10:42 pm
ANC
-
SJU
29h 20m
2 stops
Multiple Airlines Logo
2:11 am - 7:48 pm
SJU
-
ANC
21h 37m
2 stops
$901Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
American Airlines Logo
11:42 pm - 5:04 pm
ANC
-
NAS
13h 22m
2 stops
American Airlines Logo
11:02 am - 11:52 pm
NAS
-
ANC
16h 50m
2 stops
$914American Airlines
Sun, Aug 30 - Wed, Sep 2
United Airlines Logo
11:09 pm - 11:28 am
ANC
-
NAS
32h 19m
2 stops
United Airlines Logo
12:35 pm - 11:59 pm
NAS
-
ANC
15h 24m
2 stops
$957United Airlines
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.

What is the cheapest month to fly from Anchorage to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean, 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 is February, when tickets cost $226 (return) on average. On the other hand, the most expensive months are January and April, when the average cost of round-trip tickets is $1,020 and $884 respectively.

Good to know

Low seasonApril
Cheapest flight$378
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Anchorage to Santo Domingo

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 airlines flying 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 8465 reviews
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Was great in general, try to respect time and excuses when slight changes have been made, appreciated!

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports