$282 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 2/9. 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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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$931
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau1 stop$588
Puerto Plata
Puerto Plata2 stops$1,291
Punta Cana
Punta Cana2 stops$931
Santo Domingo
Santo Domingo2 stops$881
Nassau
Nassau1 stop$588
Puerto Plata
Puerto Plata2 stops$1,291

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

Sun, Mar 8 - Fri, Mar 13
American Airlines Logo
8:13 pm - 2:37 pm
ANC
-
NAS
14h 24m1 stop
American Airlines Logo
8:06 am - 7:06 pm
NAS
-
ANC
15h 00m2 stops
$588American Airlines
Sun, Mar 8 - Sat, Mar 14
American Airlines Logo
8:13 pm - 2:37 pm
ANC
-
NAS
14h 24m1 stop
American Airlines Logo
8:06 am - 7:06 pm
NAS
-
ANC
15h 00m2 stops
$593American Airlines
Tue, Jan 13 - Wed, Jan 21
United Airlines Logo
9:00 am - 3:22 pm
ANC
-
NAS
26h 22m2 stops
United Airlines Logo
3:35 pm - 11:15 pm
NAS
-
ANC
35h 40m2 stops
$613United Airlines
Sun, Mar 8 - Sun, Mar 15
United Airlines Logo
9:10 pm - 3:22 pm
ANC
-
NAS
14h 12m1 stop
United Airlines Logo
3:35 pm - 8:01 pm
NAS
-
ANC
32h 26m1 stop
$720United Airlines
Mon, Jan 12 - Thu, Jan 15
United Airlines Logo
9:00 am - 11:53 am
ANC
-
NAS
22h 53m2 stops
United Airlines Logo
3:35 pm - 11:15 pm
NAS
-
ANC
35h 40m2 stops
$724United Airlines
Sun, Mar 8 - Sun, Mar 15
United Airlines Logo
9:10 pm - 1:33 pm
ANC
-
NAS
36h 23m2 stops
United Airlines Logo
3:35 pm - 8:01 pm
NAS
-
ANC
32h 26m1 stop
$755United Airlines
Tue, Feb 24 - Sat, Mar 7
Delta Logo
9:15 pm - 3:18 pm
ANC
-
SJU
13h 03m1 stop
Delta Logo
6:15 am - 7:01 pm
SJU
-
ANC
17h 46m1 stop
$764Delta
Tue, Feb 10 - Tue, Feb 24
Alaska Airlines Logo
12:15 pm - 2:56 pm
ANC
-
SJU
21h 41m2 stops
Alaska Airlines Logo
6:00 am - 1:09 am
SJU
-
ANC
24h 09m2 stops
$776Alaska Airlines
Tue, Feb 10 - Tue, Feb 24
Multiple Airlines Logo
6:03 pm - 11:53 pm
ANC
-
SJU
48h 50m3 stops
Multiple Airlines Logo
6:00 am - 1:09 am
SJU
-
ANC
24h 09m2 stops
$803Multiple Airlines
Mon, Jan 5 - Mon, Jan 12
Multiple Airlines Logo
8:30 pm - 3:42 pm
ANC
-
POP
14h 12m2 stops
Multiple Airlines Logo
4:42 pm - 1:04 pm
POP
-
ANC
25h 22m2 stops
$1,291Multiple 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 $670, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Anchorage to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Anchorage to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Anchorage to Caribbean Islands is August, when tickets cost $441 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $1,246 and $1,079 respectively.

What’s the cheapest day of the week to fly from Anchorage to Caribbean Islands?

The average price of all round-trip flights from Anchorage to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Anchorage to Caribbean Islands, you should consider leaving on a Tuesday and avoid Thursdays if you are looking for the best rates. For your return to Anchorage, you’ll find the best rates on Mondays and the most expensive ones on Fridays.

Good to know

Low seasonAugust
Cheapest flight$282
Best time to beat the crowds with an average 56% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Anchorage to Santiago de los Caballeros

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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $1,008 on average. Morning departures are around 22% more expensive than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $1,242.

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 8021 reviews
7.9Comfort
7.3Food
8.1Boarding
8.5Crew
7.9Entertainment
Airline reviews

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

2.0 MediocreGina, Dec 2025
DTW - ELM
Read more Delta reviews

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports