$297 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 4/5. 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$1,005
Santo Domingo
Santo Domingo2 stops$813
Nassau
Nassau1 stop$664
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,144
Saint Thomas Island
Saint Thomas Island1 stop$993
Kingston
Kingston2 stops$1,177
Puerto Plata
Puerto Plata2 stops$985
Punta Cana
Punta Cana1 stop$1,005
Santo Domingo
Santo Domingo2 stops$813
Nassau
Nassau1 stop$664
Santiago de los Caballeros
Santiago de los Caballeros2 stops$1,144
Saint Thomas Island
Saint Thomas Island1 stop$993
Kingston
Kingston2 stops$1,177
Puerto Plata
Puerto Plata2 stops$985

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, Apr 27 - Sat, May 2
United Airlines Logo
8:50 pm - 2:57 pm
ANC
-
NAS
14h 07m
1 stop
United Airlines Logo
3:10 pm - 10:45 pm
NAS
-
ANC
11h 35m
1 stop
$664United Airlines
Mon, Apr 20 - Mon, Apr 27
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
$681United 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
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, Jul 22 - Tue, Aug 4
Multiple Airlines Logo
11:21 pm - 12:30 pm
ANC
-
PUJ
33h 09m
1 stop
Multiple Airlines Logo
7:10 pm - 5:19 pm
PUJ
-
ANC
26h 09m
2 stops
$1,017Multiple Airlines
Wed, Jul 8 - Mon, Jul 13
Air Canada Logo
2:40 pm - 3:20 pm
ANC
-
PUJ
44h 40m
2 stops
Air Canada Logo
5:05 pm - 1:38 pm
PUJ
-
ANC
48h 33m
2 stops
$1,110Air Canada
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
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
Sun, Mar 29 - Thu, Apr 2
Air Canada Logo
9:04 pm - 12:35 pm
ANC
-
KIN
36h 31m
2 stops
Air Canada Logo
1:55 pm - 7:48 pm
KIN
-
ANC
32h 53m
2 stops
$1,958Air Canada
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 $630, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonAugust
Cheapest flight$354
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 Punta Cana

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 8276 reviews
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
7.9Comfort
Airline reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

8.0 ExcellentMary, Mar 2026
LGA - MKE
Read more Delta reviews

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Stop changing gates. Stop cancelling flights Stop moving my seat.

Extremely disappointed with Delta. They canceled flight last minute and then I rebooked the other flights and with which were delayed as well

Could not get my connecting flight boarding pass until four hrs before departure! Ver annoying especially since the staff could not explain why!

The flight was flying with 30% capacity. The flight my seat from preferred seating to back of the seat. Even though i can understand that this was to balance the flight weight. The flight attendance decided to do the serving near my seat and in the middle , their noices woke me up from sleep , when i realized that the service has ended and when they were going back asked for a coffee, for which they answered they have completed teh service in my location. That really upset me as they woke me up and also rejected the coffee i asked. I ended up landing with a headache, thanks to the crew that screwed up my travel

Delayed. Hot. Passenger next to me was so large I couldn’t move.

Same experience as the flight from Norfolk to Atlanta where people are boarded in zones that don't make sense. People behind you on the plane will get on before you and they take the luggage space on your row.

The boarding process doesn't make sense since some people that will sit behind your rows are boarded before you and then they take up the luggage space above your head. I then have to wait for people to get off the plane before I can go back to get my luggage.

Good flight. Connector flight was delayed so made a short turnaround in Atlanta which was stressful. Otherwise, great crew, Staff in ATL was very informative about the delay and ensured people their connections were fine. Notified the ones that were not. Great communication.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Anchorage (ANC)