$387 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 8/17. 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 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$1,003
Santo Domingo
Santo Domingo2 stops$983
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,189
Kingston
Kingston2 stops$1,305
Puerto Plata
Puerto Plata2 stops$1,186
Punta Cana
Punta Cana2 stops$1,003
Santo Domingo
Santo Domingo2 stops$983
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,189
Kingston
Kingston2 stops$1,305
Puerto Plata
Puerto Plata2 stops$1,186

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

vie., may. 29 - vie., jun. 5
American Airlines Logo
9:53 pm - 4:58 pm
ANC
-
NAS
15h 05m
2 stops
American Airlines Logo
12:38 pm - 11:52 pm
NAS
-
ANC
15h 14m
2 stops
$729American Airlines
lun., may. 25 - vie., jun. 5
Delta Logo
1:55 am - 8:30 pm
ANC
-
SJU
14h 35m
2 stops
Delta Logo
7:05 am - 12:55 am
SJU
-
ANC
21h 50m
2 stops
$815Delta
vie., may. 29 - vie., jun. 5
United Airlines Logo
8:20 pm - 11:28 am
ANC
-
NAS
11h 08m
1 stop
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$829United Airlines
dom., may. 24 - mié., jun. 3
Delta Logo
8:05 pm - 12:01 pm
ANC
-
SJU
11h 56m
1 stop
Delta Logo
7:05 am - 12:55 am
SJU
-
ANC
21h 50m
2 stops
$848Delta
sáb., jun. 6 - sáb., jun. 27
Delta Logo
2:20 pm - 12:00 pm
ANC
-
SJU
17h 40m
2 stops
Delta Logo
4:21 pm - 1:23 am
SJU
-
ANC
13h 02m
1 stop
$855Delta
vie., may. 22 - vie., jun. 5
Delta Logo
9:59 pm - 2:57 pm
ANC
-
SJU
12h 58m
1 stop
Delta Logo
7:05 am - 12:55 am
SJU
-
ANC
21h 50m
2 stops
$873Delta
vie., may. 22 - sáb., may. 30
Delta Logo
9:59 pm - 2:57 pm
ANC
-
SJU
12h 58m
1 stop
Delta Logo
7:05 am - 12:25 am
SJU
-
ANC
21h 20m
2 stops
$893Delta
jue., may. 21 - mié., may. 27
Southwest Logo
10:25 pm - 11:40 pm
ANC
-
SJU
21h 15m
2 stops
Southwest Logo
5:35 am - 9:15 pm
SJU
-
ANC
19h 40m
2 stops
$900Southwest
vie., may. 29 - vie., jun. 5
American Airlines Logo
8:17 pm - 2:46 pm
ANC
-
NAS
14h 29m
1 stop
American Airlines Logo
12:42 pm - 8:41 pm
NAS
-
ANC
11h 59m
1 stop
$940American Airlines
mié., sep. 2 - dom., sep. 6
United Airlines Logo
11:59 pm - 10:46 pm
ANC
-
SDQ
18h 47m
2 stops
United Airlines Logo
6:00 am - 7:14 pm
SDQ
-
ANC
17h 14m
2 stops
$1,027United 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 $635, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$387
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 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 8404 reviews
7.9Comfort
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
Airline reviews

The gentleman at the gate I think his name is RIE was exceptional

10.0 ExcellentGireesh, Apr 2026
DCA - DTW
Read more Delta reviews

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports