$354 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 6/9. 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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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$703
Santo Domingo
Santo Domingo2 stops$1,038
Nassau
Nassau2 stops$826
Saint Thomas Island
Saint Thomas Island2 stops$1,044
Kingston
Kingston1 stop$1,155
Punta Cana
Punta Cana2 stops$703
Santo Domingo
Santo Domingo2 stops$1,038
Nassau
Nassau2 stops$826
Saint Thomas Island
Saint Thomas Island2 stops$1,044
Kingston
Kingston1 stop$1,155

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, Jun 8 - Sun, Jun 14
Air Canada Logo
2:40 pm - 4:30 pm
ANC
-
PUJ
21h 50m
2 stops
Air Canada Logo
5:25 pm - 1:36 pm
PUJ
-
ANC
24h 11m
2 stops
$703Air Canada
Thu, Oct 29 - Thu, Nov 12
United Airlines Logo
11:40 pm - 8:00 pm
ANC
-
SJU
16h 20m
2 stops
United Airlines Logo
8:10 am - 10:39 pm
SJU
-
ANC
19h 29m
2 stops
$815United Airlines
Tue, Jun 9 - Wed, Jun 17
Air Canada Logo
2:40 pm - 5:30 pm
ANC
-
NAS
22h 50m
2 stops
Air Canada Logo
6:30 pm - 1:38 pm
NAS
-
ANC
47h 08m
2 stops
$826Air Canada
Thu, Oct 1 - Thu, Oct 15
Delta Logo
2:20 pm - 11:48 am
ANC
-
SJU
17h 28m
2 stops
Delta Logo
7:30 am - 10:36 pm
SJU
-
ANC
19h 06m
2 stops
$835Delta
Thu, Oct 1 - Thu, Oct 15
American Airlines Logo
8:20 pm - 3:02 pm
ANC
-
SJU
14h 42m
1 stop
American Airlines Logo
8:35 am - 10:48 pm
SJU
-
ANC
18h 13m
2 stops
$905American Airlines
Tue, Jun 9 - Wed, Jun 17
American Airlines Logo
8:17 pm - 5:04 pm
ANC
-
NAS
16h 47m
1 stop
American Airlines Logo
11:02 am - 11:52 pm
NAS
-
ANC
16h 50m
2 stops
$914American Airlines
Fri, Jul 31 - Sat, Aug 8
Sun Country Air Logo
8:52 pm - 3:18 pm
ANC
-
SJU
14h 26m
1 stop
Sun Country Air Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$944Sun Country Air
Thu, Jul 30 - Sat, Aug 8
Southwest Logo
11:55 pm - 12:05 am
ANC
-
SJU
20h 10m
2 stops
Southwest Logo
8:20 am - 11:45 pm
SJU
-
ANC
19h 25m
2 stops
$970Southwest
Thu, May 28 - Mon, Jun 1
Southwest Logo
10:25 pm - 11:55 pm
ANC
-
SJU
21h 30m
2 stops
Southwest Logo
5:05 am - 10:45 pm
SJU
-
ANC
21h 40m
2 stops
$1,055Southwest
Wed, Jul 1 - Fri, Jul 10
Delta Logo
10:30 pm - 8:00 pm
ANC
-
KIN
18h 30m
2 stops
Delta Logo
9:00 am - 10:21 am
KIN
-
ANC
28h 21m
2 stops
$1,217Delta
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 $649, 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 April, when tickets cost $0 (return) on average. On the other hand, the most expensive months are February and May, when the average cost of round-trip tickets is $1,161 and $1,086 respectively.

Good to know

Low seasonApril
Cheapest flight$354
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Anchorage to Santo Domingo

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 airlines 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 8450 reviews
7.2Food
7.8Entertainment
8.1Boarding
7.8Comfort
8.5Crew
Airline reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

6.0 Goodrghinftl, May 2026
FWA - ATL
Read more Delta reviews

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

It was a pleasant surprise to have complimentary Wi-Fi on the flight

Much better than Latam, the worse airline company ever. I hope I don't have the need to fly Latam ever in my life again.

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Seat comfort was poor (no lumbar or lower back support).

The airplane seats were spacious and comfortable, and the flight attendants were friendly and attentive. The food was delicious like never before. The blankets and toiletries were thoughtfully provided. The captain's navigation was steady and reliable. In short, having flown with Starlux, I won't consider any other airline next time.

STOP MAKING THE SEATING SO CRAMPED. WE NEED A PASSENGER BILL OF RIGHTS!

The passenger in front of of me reclined their seat back all the way the entire flight. Their headrest was in my face the entire flight! I barely had room for the little plastic cup of water to fit on my tray table; can you make the seats and space between the rows any smaller??? You can’t even get up to use the restroom! Worst flight I’ve had in a very long time!

We had several flights and they were all on-time and flawless

My Frequent Flyer nber wasn't put on as I was told it was..... This resulted in a last group boarding and no priority tags on My bags.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Terrible steward... Plane was quite empty... I asked to move "back" in the plane and the steward said no... Unnecessary power trip of mediocre people.

Flight was delayed an no one cares, or try to help passengers to get the conexión.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports