$382 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 9/15. 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
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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$1,069
Santo Domingo
Santo Domingo2 stops$1,000
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,044
Kingston
Kingston2 stops$1,247
Punta Cana
Punta Cana1 stop$1,069
Santo Domingo
Santo Domingo2 stops$1,000
Nassau
Nassau2 stops$729
Saint Thomas Island
Saint Thomas Island2 stops$1,044
Kingston
Kingston2 stops$1,247

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

Tue, Aug 11 - Mon, Aug 17
American Airlines Logo
11:41 pm - 7:49 pm
ANC
-
NAS
16h 08m
2 stops
American Airlines Logo
10:36 am - 10:32 pm
NAS
-
ANC
15h 56m
2 stops
$729American Airlines
Sun, Aug 16 - Sat, Aug 22
Southwest Logo
11:55 pm - 10:50 pm
ANC
-
SJU
18h 55m
2 stops
Southwest Logo
5:55 am - 9:15 pm
SJU
-
ANC
19h 20m
2 stops
$825Southwest
Sun, Oct 18 - Mon, Nov 2
Delta Logo
11:30 am - 1:21 pm
ANC
-
SJU
21h 51m
2 stops
Delta Logo
1:46 pm - 1:45 am
SJU
-
ANC
16h 59m
2 stops
$835Delta
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
10:19 pm - 11:28 am
ANC
-
NAS
33h 09m
2 stops
United Airlines Logo
12:35 pm - 11:59 pm
NAS
-
ANC
15h 24m
2 stops
$849United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
10:19 pm - 11:28 am
ANC
-
NAS
33h 09m
2 stops
United Airlines Logo
12:35 pm - 7:59 pm
NAS
-
ANC
35h 24m
2 stops
$880United Airlines
Mon, Aug 24 - Thu, Aug 27
United Airlines Logo
10:19 pm - 11:28 am
ANC
-
NAS
33h 09m
2 stops
United Airlines Logo
2:35 pm - 7:11 pm
NAS
-
ANC
32h 36m
1 stop
$885United Airlines
Sun, Jul 26 - Sat, Aug 8
JetBlue Logo
8:10 pm - 11:40 am
ANC
-
SJU
11h 30m
1 stop
JetBlue Logo
7:00 am - 7:00 pm
SJU
-
ANC
16h 00m
1 stop
$887JetBlue
Thu, Jul 2 - Sat, Jul 11
Multiple Airlines Logo
8:52 pm - 12:37 am
ANC
-
SJU
23h 45m
2 stops
Multiple Airlines Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$931Multiple Airlines
Mon, Jul 27 - Sat, Aug 8
Multiple Airlines Logo
8:52 pm - 11:16 am
ANC
-
SJU
34h 24m
2 stops
Multiple Airlines Logo
4:20 pm - 12:18 pm
SJU
-
ANC
23h 58m
1 stop
$1,001Multiple Airlines
Wed, Jun 10 - Fri, Jul 3
Delta Logo
10:02 pm - 6:04 pm
ANC
-
SDQ
16h 02m
2 stops
Delta Logo
7:35 pm - 4:15 pm
SDQ
-
ANC
24h 40m
2 stops
$1,082Delta
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 $647, 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$467
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 San Juan

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 8434 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.2Food
7.8Entertainment
Airline reviews

Planes were clean, no water or snacks on either flight.

6.0 GoodAnonymous, May 2026
ECP - ATL
Read more Delta reviews

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

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.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

This flight is a quick way to get to Chicago, but a bit expensive.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports