$368 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 5/14. 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$1,028
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$708
Kingston
Kingston2 stops$1,225
Puerto Plata
Puerto Plata2 stops$1,123
Punta Cana
Punta Cana1 stop$1,028
Santo Domingo
Santo Domingo1 stop$943
Nassau
Nassau2 stops$708
Kingston
Kingston2 stops$1,225
Puerto Plata
Puerto Plata2 stops$1,123

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

ds., juny 6 - ds., juny 13
Air Canada Logo
2:40 pm - 5:30 pm
ANC
-
NAS
22h 50m
2 stops
Air Canada Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
2 stops
$708Air Canada
dg., maig 17 - dg., maig 24
United Airlines Logo
8:45 pm - 2:57 pm
ANC
-
NAS
14h 12m
1 stop
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$780United Airlines
ds., juny 6 - ds., juny 13
Multiple Airlines Logo
1:22 pm - 7:15 pm
ANC
-
NAS
25h 53m
3 stops
Multiple Airlines Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
2 stops
$830Multiple Airlines
dg., maig 17 - dg., maig 24
Southwest Logo
11:55 pm - 11:40 pm
ANC
-
SJU
19h 45m
2 stops
Southwest Logo
5:45 am - 10:45 pm
SJU
-
ANC
21h 00m
2 stops
$835Southwest
dv., maig 15 - ds., maig 23
United Airlines Logo
11:49 pm - 4:10 pm
ANC
-
NAS
12h 21m
1 stop
United Airlines Logo
4:58 pm - 11:10 am
NAS
-
ANC
22h 12m
2 stops
$849United Airlines
ds., juny 6 - dv., juny 26
Delta Logo
9:59 pm - 4:29 pm
ANC
-
SJU
14h 30m
2 stops
Delta Logo
2:41 pm - 1:55 am
SJU
-
ANC
15h 14m
2 stops
$875Delta
dj., jul.. 9 - dg., jul.. 12
American Airlines Logo
9:55 pm - 11:51 pm
ANC
-
SJU
21h 56m
1 stop
American Airlines Logo
6:00 am - 8:48 pm
SJU
-
ANC
18h 48m
2 stops
$935American Airlines
ds., juny 6 - dj., juny 25
American Airlines Logo
9:53 pm - 11:56 pm
ANC
-
SJU
22h 03m
1 stop
American Airlines Logo
12:59 am - 8:41 pm
SJU
-
ANC
23h 42m
1 stop
$950American Airlines
dv., jul.. 24 - dc., ag. 5
Delta Logo
5:20 pm - 12:11 pm
ANC
-
STT
14h 51m
2 stops
Delta Logo
1:21 pm - 1:29 am
STT
-
ANC
16h 08m
2 stops
$954Delta
ds., juny 6 - ds., juny 13
Multiple Airlines Logo
1:22 pm - 7:15 pm
ANC
-
NAS
25h 53m
3 stops
Multiple Airlines Logo
6:30 pm - 1:36 pm
NAS
-
ANC
23h 06m
3 stops
$1,157Multiple 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$368
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 8430 reviews
8.5Crew
7.8Entertainment
7.9Comfort
8.1Boarding
7.2Food
Airline reviews

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

4.0 OkayDerek, Apr 2026
SEA - HNL
Read more Delta reviews

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports