$412 Find Cheap Flights from Anchorage to Caribbean Islands

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 6/29. 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
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.

Bundle and saveSave money when you bundle your flight + hotel.

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

Flight Deals
Booking Insights
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$753
Santo Domingo
Santo Domingo2 stops$961
Nassau
Nassau1 stop$1,114
Kingston
Kingston2 stops$1,352
Punta Cana
Punta Cana2 stops$753
Santo Domingo
Santo Domingo2 stops$961
Nassau
Nassau1 stop$1,114
Kingston
Kingston2 stops$1,352

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

Mon, Jun 8 - Sun, Jun 14
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
$753Air Canada
Wed, Jun 10 - Wed, Jun 17
Air Canada Logo
2:40 pm - 4:30 pm
ANC
-
PUJ
21h 50m
2 stops
Air Canada Logo
5:25 pm - 1:38 pm
PUJ
-
ANC
48h 13m
2 stops
$771Air Canada
Mon, Oct 5 - Sat, Oct 17
Delta Logo
11:30 am - 11:56 am
ANC
-
SJU
20h 26m
2 stops
Delta Logo
7:30 am - 10:36 pm
SJU
-
ANC
19h 06m
2 stops
$835Delta
Thu, Jul 9 - Mon, Jul 13
Delta Logo
10:10 pm - 4:45 pm
ANC
-
SJU
14h 35m
2 stops
Delta Logo
2:21 pm - 1:54 am
SJU
-
ANC
15h 33m
2 stops
$855Delta
Sun, Sep 20 - Sun, Sep 27
American Airlines Logo
8:20 pm - 3:02 pm
ANC
-
SJU
14h 42m
1 stop
American Airlines Logo
7:05 pm - 7:08 pm
SJU
-
ANC
28h 03m
2 stops
$895American Airlines
Wed, Jun 3 - Wed, Jun 10
Southwest Logo
11:55 pm - 11:35 pm
ANC
-
SJU
19h 40m
2 stops
Southwest Logo
10:00 am - 10:45 pm
SJU
-
ANC
16h 45m
2 stops
$940Southwest
Mon, Oct 5 - Sat, Oct 24
American Airlines Logo
8:20 pm - 2:20 pm
ANC
-
SDQ
14h 00m
2 stops
American Airlines Logo
8:00 am - 7:08 pm
SDQ
-
ANC
15h 08m
2 stops
$961American Airlines
Fri, Jun 5 - Sat, Jun 27
Multiple Airlines Logo
1:22 pm - 12:41 am
ANC
-
SJU
31h 19m
2 stops
Multiple Airlines Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$964Multiple Airlines
Fri, Jun 5 - Sat, Jun 27
Southwest Logo
10:25 pm - 8:35 pm
ANC
-
SJU
18h 10m
2 stops
Southwest Logo
7:00 am - 9:15 pm
SJU
-
ANC
18h 15m
2 stops
$990Southwest
Sat, Jun 6 - Sat, Jun 27
Multiple Airlines Logo
1:22 pm - 1:15 pm
ANC
-
SJU
43h 53m
2 stops
Multiple Airlines Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$1,024Multiple 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 $644, 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 $1,086 respectively.

Good to know

Low seasonApril
Cheapest flight$412
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 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 airlines flying 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.
7.9
DeltaOverall score based on 8456 reviews
7.9Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

10.0 ExcellentIrmara, May 2026
MCO - BOS
Read more Delta reviews

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

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.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

The flight attendant on my side of business class seemed like a novice and did not provide good service. Otherwise the flight was good and the entertainment system was very good. No free WiFi.

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports