$298 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 6/25. 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 Cana2 stops$1,026
Santo Domingo
Santo Domingo2 stops$1,163
Nassau
Nassau1 stop$709
Kingston
Kingston2 stops$1,225
Punta Cana
Punta Cana2 stops$1,026
Santo Domingo
Santo Domingo2 stops$1,163
Nassau
Nassau1 stop$709
Kingston
Kingston2 stops$1,225

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

qui, mai 21 - qui, mai 28
United Airlines Logo
10:29 pm - 1:47 pm
ANC
-
NAS
11h 18m
1 stop
United Airlines Logo
3:59 pm - 11:10 am
NAS
-
ANC
23h 11m
2 stops
$709United Airlines
qui, mai 21 - qui, mai 28
American Airlines Logo
8:17 pm - 5:05 pm
ANC
-
NAS
16h 48m
1 stop
American Airlines Logo
12:47 pm - 8:47 pm
NAS
-
ANC
12h 00m
1 stop
$804American Airlines
qui, mai 21 - qui, mai 28
American Airlines Logo
9:53 pm - 5:50 pm
ANC
-
NAS
15h 57m
2 stops
American Airlines Logo
10:17 am - 10:35 pm
NAS
-
ANC
16h 18m
2 stops
$809American Airlines
qua, set 9 - qua, out 21
Delta Logo
2:20 pm - 12:13 pm
ANC
-
SJU
17h 53m
2 stops
Delta Logo
7:30 am - 10:36 pm
SJU
-
ANC
19h 06m
2 stops
$815Delta
qua, jul 15 - seg, jul 20
American Airlines Logo
9:55 pm - 3:04 pm
ANC
-
NAS
13h 09m
2 stops
American Airlines Logo
12:29 pm - 8:48 pm
NAS
-
ANC
12h 19m
1 stop
$830American Airlines
qua, jul 15 - seg, jul 20
American Airlines Logo
9:55 pm - 6:10 pm
ANC
-
NAS
16h 15m
2 stops
American Airlines Logo
12:29 pm - 8:48 pm
NAS
-
ANC
12h 19m
1 stop
$832American Airlines
sex, mai 22 - qua, jun 10
Delta Logo
1:55 am - 10:17 pm
ANC
-
SJU
16h 22m
2 stops
Delta Logo
2:04 pm - 1:23 am
SJU
-
ANC
15h 19m
2 stops
$835Delta
qua, jul 22 - qui, jul 30
Multiple Airlines Logo
11:21 pm - 12:30 pm
ANC
-
PUJ
33h 09m
1 stop
Multiple Airlines Logo
11:42 am - 1:37 am
PUJ
-
ANC
17h 55m
2 stops
$1,040Multiple Airlines
qua, jul 22 - qui, jul 30
Multiple Airlines Logo
11:21 pm - 12:30 pm
ANC
-
PUJ
33h 09m
1 stop
Multiple Airlines Logo
11:42 am - 1:37 am
PUJ
-
ANC
17h 55m
2 stops
$1,060Multiple Airlines
seg, jun 8 - sex, jun 19
Air Canada Logo
2:40 pm - 3:25 pm
ANC
-
PUJ
44h 45m
2 stops
Air Canada Logo
5:05 pm - 1:38 pm
PUJ
-
ANC
48h 33m
2 stops
$1,160Air 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 $629, prices are generally cheapest when you fly direct.

Good to know

Low seasonApril
Cheapest flight$298
Best time to beat the crowds with an average 11% 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 8388 reviews
7.2Food
8.5Crew
7.8Entertainment
7.9Comfort
8.1Boarding
Airline reviews

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

10.0 ExcellentSarah, Apr 2026
LAX - SFO
Read more Delta reviews

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports