$253 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 5/26. 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$974
Santo Domingo
Santo Domingo2 stops$892
Nassau
Nassau1 stop$664
Kingston
Kingston2 stops$1,489
Punta Cana
Punta Cana1 stop$974
Santo Domingo
Santo Domingo2 stops$892
Nassau
Nassau1 stop$664
Kingston
Kingston2 stops$1,489

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

Sat, May 16 - Sun, May 24
United Airlines Logo
11:59 pm - 2:57 pm
ANC
-
NAS
10h 58m
1 stop
United Airlines Logo
2:53 pm - 11:10 am
NAS
-
ANC
24h 17m
2 stops
$664United Airlines
Sat, May 16 - Sun, May 24
United Airlines Logo
11:59 pm - 2:57 pm
ANC
-
NAS
10h 58m
1 stop
United Airlines Logo
2:53 pm - 7:00 pm
NAS
-
ANC
32h 07m
1 stop
$734United Airlines
Sun, Mar 1 - Tue, Mar 10
Delta Logo
1:15 pm - 1:05 pm
ANC
-
SJU
18h 50m
2 stops
Delta Logo
7:30 am - 6:51 pm
SJU
-
ANC
15h 21m
2 stops
$765Delta
Thu, Mar 26 - Fri, Apr 3
American Airlines Logo
8:13 pm - 5:11 pm
ANC
-
SJU
16h 58m
2 stops
American Airlines Logo
6:33 am - 7:06 pm
SJU
-
ANC
16h 33m
1 stop
$845American Airlines
Sat, Apr 18 - Sun, May 3
Delta Logo
8:25 pm - 4:23 pm
ANC
-
SJU
15h 58m
1 stop
Delta Logo
6:15 am - 8:37 pm
SJU
-
ANC
18h 22m
2 stops
$850Delta
Wed, Mar 18 - Tue, Mar 24
American Airlines Logo
8:13 pm - 10:31 pm
ANC
-
SJU
22h 18m
1 stop
American Airlines Logo
6:33 am - 7:06 pm
SJU
-
ANC
16h 33m
1 stop
$865American Airlines
Thu, Jul 9 - Sun, Jul 12
Multiple Airlines Logo
4:09 pm - 12:30 pm
ANC
-
PUJ
16h 21m
2 stops
Multiple Airlines Logo
6:00 pm - 4:44 am
PUJ
-
ANC
14h 44m
1 stop
$1,023Multiple Airlines
Mon, Mar 2 - Mon, Mar 9
Multiple Airlines Logo
5:00 pm - 2:04 pm
ANC
-
SDQ
16h 04m
2 stops
Multiple Airlines Logo
5:50 pm - 7:06 pm
SDQ
-
ANC
29h 16m
2 stops
$1,087Multiple Airlines
Mon, Mar 30 - Wed, Apr 1
Air Canada Logo
9:04 pm - 12:25 pm
ANC
-
NAS
35h 21m
2 stops
Air Canada Logo
9:10 pm - 7:55 pm
NAS
-
ANC
26h 45m
2 stops
$1,098Air Canada
Mon, Mar 30 - Wed, Apr 1
Air Canada Logo
9:04 pm - 12:25 pm
ANC
-
NAS
35h 21m
2 stops
Air Canada Logo
9:10 pm - 7:55 pm
NAS
-
ANC
26h 45m
2 stops
$1,101Air 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 $644, prices are generally cheapest when you fly direct.

Good to know

Low seasonAugust
Cheapest flight$253
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 Nassau

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 8138 reviews
7.9Comfort
7.8Entertainment
8.1Boarding
7.2Food
8.5Crew
Airline reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

2.0 MediocreAlparda, Feb 2026
BOS - ICN
Read more Delta reviews

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports