$370 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 4/15. 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$1,022
Santo Domingo
Santo Domingo2 stops$962
Nassau
Nassau2 stops$709
Saint Thomas Island
Saint Thomas Island2 stops$1,039
Kingston
Kingston2 stops$1,197
Punta Cana
Punta Cana2 stops$1,022
Santo Domingo
Santo Domingo2 stops$962
Nassau
Nassau2 stops$709
Saint Thomas Island
Saint Thomas Island2 stops$1,039
Kingston
Kingston2 stops$1,197

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

Tue, Jun 2 - Tue, Jul 21
American Airlines Logo
7:00 am - 11:39 pm
ANC
-
SJU
12h 39m
1 stop
American Airlines Logo
5:45 am - 6:30 pm
SJU
-
ANC
16h 45m
1 stop
$675American Airlines
Tue, Jun 2 - Tue, Jun 9
American Airlines Logo
9:53 pm - 5:50 pm
ANC
-
NAS
15h 57m
2 stops
American Airlines Logo
12:38 pm - 11:52 pm
NAS
-
ANC
15h 14m
2 stops
$709American Airlines
Sun, Apr 5 - Mon, Apr 13
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:59 pm - 7:48 pm
NAS
-
ANC
31h 49m
1 stop
$740United Airlines
Sun, Apr 5 - Mon, Apr 13
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:59 pm - 10:45 pm
NAS
-
ANC
34h 46m
2 stops
$750United Airlines
Sun, Aug 23 - Sun, Sep 6
Southwest Logo
11:15 pm - 8:05 pm
ANC
-
SJU
16h 50m
2 stops
Southwest Logo
6:00 am - 10:05 pm
SJU
-
ANC
20h 05m
2 stops
$775Southwest
Tue, Aug 4 - Tue, Aug 18
Southwest Logo
11:15 pm - 10:00 pm
ANC
-
SJU
18h 45m
2 stops
Southwest Logo
10:30 am - 10:05 pm
SJU
-
ANC
15h 35m
2 stops
$790Southwest
Thu, Apr 23 - Thu, May 14
Delta Logo
3:45 pm - 7:33 pm
ANC
-
STI
23h 48m
2 stops
Delta Logo
6:00 am - 12:55 am
STI
-
ANC
22h 55m
2 stops
$1,162Delta
Thu, Apr 23 - Thu, May 14
Delta Logo
9:15 pm - 7:33 pm
ANC
-
STI
18h 18m
2 stops
Delta Logo
8:59 pm - 1:14 pm
STI
-
ANC
20h 15m
2 stops
$1,202Delta
Fri, May 15 - Sat, May 30
Multiple Airlines Logo
2:40 pm - 2:30 pm
ANC
-
KIN
20h 50m
3 stops
Multiple Airlines Logo
3:30 pm - 1:36 pm
KIN
-
ANC
25h 06m
2 stops
$1,545Multiple Airlines
Fri, May 15 - Sat, May 30
Multiple Airlines Logo
2:40 pm - 2:30 pm
ANC
-
KIN
20h 50m
3 stops
Multiple Airlines Logo
3:30 pm - 1:36 pm
KIN
-
ANC
25h 06m
3 stops
$1,581Multiple 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 $620, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$370
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 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 airline 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 8303 reviews
7.9Comfort
8.5Crew
7.8Entertainment
7.2Food
8.1Boarding
Airline reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

6.0 GoodCarl, Mar 2026
ATL - ATW
Read more Delta reviews

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports