$328 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 3/30. 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 Cana1 stop$984
Santo Domingo
Santo Domingo2 stops$813
Nassau
Nassau1 stop$664
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,000
Saint Thomas Island
Saint Thomas Island1 stop$993
Kingston
Kingston2 stops$1,174
Puerto Plata
Puerto Plata2 stops$982
Punta Cana
Punta Cana1 stop$984
Santo Domingo
Santo Domingo2 stops$813
Nassau
Nassau1 stop$664
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,000
Saint Thomas Island
Saint Thomas Island1 stop$993
Kingston
Kingston2 stops$1,174
Puerto Plata
Puerto Plata2 stops$982

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

Fri, Apr 17 - Fri, Apr 24
United Airlines Logo
11:47 pm - 4:10 pm
ANC
-
NAS
12h 23m
1 stop
United Airlines Logo
2:53 pm - 7:48 pm
NAS
-
ANC
32h 55m
2 stops
$664United Airlines
Fri, Apr 17 - Fri, Apr 24
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
$680United Airlines
Sat, Apr 25 - Sat, May 2
American Airlines Logo
8:30 pm - 2:44 pm
ANC
-
NAS
14h 14m
1 stop
American Airlines Logo
3:44 pm - 6:50 pm
NAS
-
ANC
31h 06m
1 stop
$684American Airlines
Mon, Apr 20 - Mon, Apr 27
American Airlines Logo
8:30 pm - 4:34 pm
ANC
-
NAS
16h 04m
2 stops
American Airlines Logo
3:44 pm - 6:50 pm
NAS
-
ANC
31h 06m
1 stop
$688American Airlines
Tue, Jul 21 - Wed, Aug 19
Southwest Logo
11:20 pm - 7:45 pm
ANC
-
SJU
16h 25m
2 stops
Southwest Logo
10:30 am - 10:05 pm
SJU
-
ANC
15h 35m
2 stops
$770Southwest
Sat, May 9 - Sat, Jun 13
Multiple Airlines Logo
2:26 am - 9:45 pm
ANC
-
SDQ
15h 19m
2 stops
Multiple Airlines Logo
6:10 am - 1:30 pm
SDQ
-
ANC
35h 20m
1 stop
$813Multiple Airlines
Wed, May 20 - Fri, May 29
Southwest Logo
11:55 pm - 11:55 pm
ANC
-
SJU
20h 00m
2 stops
Southwest Logo
5:35 am - 10:45 pm
SJU
-
ANC
21h 10m
2 stops
$855Southwest
Tue, Jul 7 - Sun, Jul 19
Multiple Airlines Logo
12:15 pm - 10:20 am
ANC
-
PUJ
18h 05m
2 stops
Multiple Airlines Logo
6:00 pm - 4:44 am
PUJ
-
ANC
14h 44m
1 stop
$1,008Multiple Airlines
Wed, Jul 15 - Tue, Aug 18
Delta Logo
12:55 am - 11:55 pm
ANC
-
SDQ
19h 00m
2 stops
Delta Logo
2:37 pm - 10:03 am
SDQ
-
ANC
23h 26m
2 stops
$1,162Delta
Fri, Jun 5 - Sun, Jun 21
Delta Logo
5:22 pm - 6:01 pm
ANC
-
SDQ
20h 39m
2 stops
Delta Logo
6:00 am - 11:56 pm
SDQ
-
ANC
21h 56m
2 stops
$1,182Delta
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 $632, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonAugust
Cheapest flight$328
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from Anchorage to Santo Domingo

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 8271 reviews
8.1Boarding
8.5Crew
7.2Food
7.9Comfort
7.8Entertainment
Airline reviews

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

10.0 ExcellentGary, Mar 2026
LGA - DTW
Read more Delta reviews

The flight went very well, but the flight attendants didn't serve and food or drinks other than 1st class due to rough air but to be honest it wasn't that bumpy and I felt that they could've at least offered water and coffee perhaps. Also serving 1st class only is a bad look. I've been in 1st class many times and I would've felt that if the turbulence was too rough for the main cabin, it would be too rough for 1st class too.

There was an unruly family behind us that made the short flight miserable!!! The cabin crew did nothing to contain it.

My seatback screen didn’t work so that sucked because that’s what I was going to do on the plane.

Left a few minutes early. Got in 15 minutes early. Very attentive service on board. Very organized boarding.

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Anchorage (ANC)