$347 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 6/15. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$762
Santo Domingo
Santo Domingo2 stops$961
Nassau
Nassau2 stops$837
Saint Thomas Island
Saint Thomas Island2 stops$1,009
Kingston
Kingston2 stops$1,061
Puerto Plata
Puerto Plata2 stops$1,451
Punta Cana
Punta Cana2 stops$762
Santo Domingo
Santo Domingo2 stops$961
Nassau
Nassau2 stops$837
Saint Thomas Island
Saint Thomas Island2 stops$1,009
Kingston
Kingston2 stops$1,061
Puerto Plata
Puerto Plata2 stops$1,451

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 1 - Sun, Jun 14
Air Canada Logo
2:40 pm - 3:25 pm
ANC
-
PUJ
20h 45m
2 stops
Air Canada Logo
4:25 pm - 1:36 pm
PUJ
-
ANC
25h 11m
2 stops
$762Air Canada
Wed, Sep 2 - Tue, Sep 15
United Airlines Logo
8:19 pm - 11:57 am
ANC
-
SJU
11h 38m
1 stop
United Airlines Logo
1:00 am - 2:13 pm
SJU
-
ANC
17h 13m
2 stops
$815United Airlines
Sun, Oct 18 - Mon, Nov 2
Delta Logo
2:20 pm - 11:36 am
ANC
-
SJU
17h 16m
2 stops
Delta Logo
7:00 am - 1:45 am
SJU
-
ANC
23h 45m
2 stops
$835Delta
Sun, Aug 9 - Mon, Aug 17
American Airlines Logo
11:41 pm - 7:49 pm
ANC
-
NAS
16h 08m
2 stops
American Airlines Logo
10:36 am - 11:48 pm
NAS
-
ANC
17h 12m
2 stops
$837American Airlines
Mon, Jul 27 - Sat, Aug 8
Southwest Logo
10:25 pm - 6:25 pm
ANC
-
SJU
16h 00m
2 stops
Southwest Logo
8:20 am - 11:45 pm
SJU
-
ANC
19h 25m
2 stops
$845Southwest
Sun, Oct 18 - Mon, Nov 2
United Airlines Logo
11:40 pm - 8:38 pm
ANC
-
SJU
16h 58m
2 stops
United Airlines Logo
8:30 am - 7:45 pm
SJU
-
ANC
16h 15m
2 stops
$847United Airlines
Tue, Jul 28 - Sun, Aug 9
Southwest Logo
11:55 pm - 7:45 pm
ANC
-
SJU
15h 50m
2 stops
Southwest Logo
6:00 am - 10:05 pm
SJU
-
ANC
20h 05m
2 stops
$875Southwest
Mon, Jul 27 - Sat, Aug 8
JetBlue Logo
8:10 pm - 1:32 pm
ANC
-
SJU
13h 22m
1 stop
JetBlue Logo
6:48 am - 7:02 pm
SJU
-
ANC
16h 14m
1 stop
$887JetBlue
Fri, Oct 16 - Fri, Oct 30
American Airlines Logo
8:20 pm - 7:55 pm
ANC
-
SDQ
19h 35m
2 stops
American Airlines Logo
8:00 am - 7:08 pm
SDQ
-
ANC
15h 08m
2 stops
$961American Airlines
Mon, Aug 10 - Mon, Aug 17
Delta Logo
8:24 pm - 11:51 am
ANC
-
NAS
11h 27m
1 stop
Delta Logo
1:16 pm - 11:59 pm
NAS
-
ANC
14h 43m
2 stops
$1,111Delta
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 $641, 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 June and February, when the average cost of round-trip tickets is $1,171 and $1,161 respectively.

Good to know

Low seasonApril
Cheapest flight$347
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from Anchorage to Nagua

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 3 airlines serving 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 8455 reviews
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
7.8Comfort
Airline reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

10.0 Excellentangela, May 2026
LGA - PBI
Read more Delta reviews

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

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.

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

No complaints other than luggage carousel was incorrectly guiding passengers to the wrong carousel on the screen.

Did not like that we couldn't complete check in on-line without providing pictures of our passports. Worry about identity theft. We had no delays and boarding was handled In an efficient manner.

We were a little disappointed to not be able to complete check in online without uploading pics of passports. Also we have KTN's and they weren't on our boarding passes when we got to security. Had to trek back to counter to have them fix.

Excellent service in Polaris class IAD to ZRH. Arrived rested and well fed after the overnight flight.

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

Excellent! I got to Munich and was transferred to my Lufthansa flight quickly, in 15 to 20 minutes, so I did not miss my flight. However, I had checked my overhead bag at the boarding gate in Tampa. That got to Tunis the next day. That is to be expected.

It's a short hop. My carryon was checked at the gate, I didn't have to drag it all over the airport. Excellent wheelchair assist.

WiFi didn’t exist , seats were super cramped, lights stayed on near my seat for a long time while others were dimmed, the food/trash/drink cart hit my shoulder at least a couple of times while moving, food options were down to just one option by the time it got to my row, the utensils were garbage (knife bent at a couple of places by the time I was done eating) the spoon was very flimsy plastic

Friendliest Flight Attendant I’ve seen since I flew on Southwest Airlines. The whole trip was outstanding…and arrived Early!

The wifi experience is awful. I had to try again and again, taking over 30 minutes, to connect to the wifi. I had to watch the same two ads over and over until I was finally successful. Once connected, it was anything but "high speed" and disconnected at least three times during the flight.

Fine. Nothing to write home about. The plane left on time, and arrived on time.

I was downgraded from first class to coach due to an airplane change. They pulled me out of line and I was the very last person to board the plane stuck in the middle seat with no overhead place to put my carry-.on. Very poor customer service.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports